Home Vacation Home Rentals By Owner In Wintergreen Resort, VA

Showing 60 Of 126 Vacation Rentals
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Exceptional(20)

$434.15

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Private Vacation Home

Private Mountain Lodge with Panorama Views

Wintergreen Resort, Virginia, United States

This 4 bedroom / 3 bathroom beautiful mountain chalet with gorgeous panorama views offers ample space inside and out! Located on a private culdesac with nearly 4 acres and a long and flat driveway, you will be able to relax, unwind and explore with family and friends. We are less than a mile from the Wintergreen Lodge with access to restaurants, a deli/convenience store, and coffee shop.brbrThis home’s full renovation was just completed! Through the front door, you will enter into a stunning great room with a large stone fireplace. The updated kitchen comes with full size refrigerator, range, and dishwasher; stone countertops, coffee maker, toaster, microwave, Keurig, and wine fridge. The kitchen bar seats at least 4. The dining room table can seat 8, and the sunroom game table seats 4. brbrbrThere is a separate wing on the main floor with two bedrooms (Queen and 2-twin beds) and full bath. Upstairs, you will find the owner's bedroom (King) and bathroom. Downstairs is a large mudroom and laundry room, perfect for storing ski or hiking equipment as well as another full bath and large bedroom (King and 2-twin beds). The bedrooms boast beautiful mountain views and plenty of privacy.brbrThe sunroom includes a 14-foot Shuffleboard table and another large smart TV. brbrA very unique position on the mountain provides amazing sunrise and sunset views from the Great Room and two side porches. brbrThere is a large 55-inch TV in the great room as well as 2 smart tvs in the home.brbrAlso includes two convertible kid chairs that can serve as sleeping cots or just a cozy place to watch a movie. brbrFully stocked kitchen, games, puzzles and books. Nice bedding and linens. It has everything you need to relax, unwind and enjoy the gorgeous Blue Ridge mountains!
Bed 4

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Bath 3

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Sleep 10

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Exceptional(32)

$289.73

/ Nightly
Private Vacation Home

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Wintergreen Resort, Virginia, United States

Welcome to Blackrock Escape! Our home is the perfect getaway for couples and small families. brbr*Sleeps 4: Two King beds w/ Helix mattresses br*Wood burning fireplace *Hot tub br*Two decks *Gas grill br*Fast wifi *Smart TVsbr*Dogs Ok brbrWalk to hiking trails – the Plunge Trail at Blackrock Park is only a two-minute walk from the house. Three minute drive to the Mountain Inn and skiing. Endless activities await – hiking, cideries/breweries/wineries/distilleries, skiing, tubing...brbrHappy dog fee for first dog is $75/stay. Second dog considered on a case by case basis. If second dog is approved, an additional $75 fee will be collected separately after reservation is confirmed.brbrThe SpacebrbrOutside:brThere are two back decks for you to enjoy. The upper deck has a gas grill and table and chairs. The hot tub is on the lower deck – directly accessible from both bedrooms. brbrLiving Room:brSo many ways to relax – watch your favorite show or movie on the 65” smart TV, play a game, do a puzzle, enjoy the wood burning fireplace. (Note: Guests must provide their own firewood. We recommend purchasing firewood at The Market at Wintergreen Resort – two-minute drive from the house.)brbrBedroom One:brComfortable King bed w/ Helix mattress. En suite bathroom – with a tub/shower combo (early 80s vibe in bathroom is complimentary). 50” smart TV.brbrBedroom Two: brComfortable King bed w/ Helix mattress. En suite bathroom – with a tub/shower combo (early 80s vibe in bathroom is complimentary). 43” smart TV.brbrKitchen:brThe kitchen includes a Keurig K-Duo (single-serve and traditional coffee maker), Chemex pour-over coffee maker, dishwasher, microwave, crock pot, blender, hand mixer, pots, pans, baking sheets, baking dishes, and bowls. brbrLaundry: Full-sized washing machine and dryerbrbrAdditional Highlights/Amenities:br*Keyless accessbr*Hair dryersbr*Charging stations on nightstandsbr*Iron/ironing boardbr*Swim towels for hot tubbrbrGuest Access: Guests will be provided with a unique access code for keyless entry to the front door prior to arrival.brbrOther Things To Note:brbrThe house has one Ring floodlight camera in the front (covers the driveway and approach to front door area). brbrThe owner's storage area in the loft (accessed via the spiral staircase in the dining room) is not accessible to guests. brbrCertain Resort amenities are not available to anyone renting through VRBO. There is no guest access to The Aquatics + Fitness Center (indoor pool/fitness center), Devil's Knob golf course (on the mountain), Devil's Grill, or the Racquet Sports Facilities. The Resort does not currently offer day passes for purchase. (Note: Please contact Wintergreen Resort directly with any questions regarding access to specific Resort amenities.)brbrSeasonal resort activities (available for an additional fee) include: skiing, The Plunge Tubing Park, The Spa at Wintergreen, Discovery Ridge Adventure Center, The Treehouse, Stoney Creek golf course (in the valley), and on-site dining.brbrAccess to Lake Monocan (Sun, Mon, Wed, Thu, and Fri) is available for a fee. There are also a number of great hiking trails in/around Wintergreen.brbrGuests have free access to Chestnut Springs outdoor pool from 2pm - close daily (between Memorial Day and Labor Day) .
Bed 2

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Bath 2

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Sleep 4

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Exceptional(8)

$363.89

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Private Vacation Home

Beautiful 3 Bedroom Mountain House Private Sauna and Hottub

Wintergreen Resort, Virginia, United States

Nestled among the trees, The Bear’s Perch is a cozy treetop retreat with a stone fireplace, spacious decks, and forest views. Sleeps 8+ with 3 bedrooms, 2.5 baths, and an extra bonus room. Only a 4-minute walk to the wintergreen slopes. hiking trails, and mountain overlooks. A warm, quiet escape to relax, gather with the New addition of a Sauna and Hottub Both with incredible Views tons to do in the summertime.
Bed 3

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Bath 3

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Sleep 8

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Exceptional(3)

$596.57

/ Nightly
Private Vacation Home

Rock Climb Wall, “Treehouse” Suite, Hot Tub, Blue Ridge Views, Sleeps 14

Wintergreen Resort, Virginia, United States

Escape to the mountains at this 5BR/4.5BA home in Wintergreen Resort! Enjoy breathtaking Blue Ridge Mountain views, cozy evenings by the firepit, hot tub, and direct trail access to the Old Appalachian Trail right from your backyard. Perfect for families, groups, and outdoor lovers.brbrSpacious & Fun: Two living areas offer plenty of room to relax and play. The main level features a bright open-concept living space with plenty of couches for the family, while the lower level includes a rock climbing wall a hit with kids and kids-at-heart! There are 4 bedrooms in the main house and one bedroom in the treehouse above the garage. brbrGather Together: The large kitchen is fully equipped for group cooking and flows into a dining area with seating for 14 - perfect for family meals and game nights. After exploring, unwind on the deck with a glass of wine and take in the mountain sunset.brbrSleeping Arrangements: 4 bedrooms in the main house and 1 bedroom in the treehouse. br• 2 upstairs in main house: King bed w/ ensuite bathroom + twin bunk bed roombr• 2 downstairs in main house: King bed w/ ensuite bathroom + 2 twin bunk beds room w/ bathroom outside roombr• 1 treehouse: King bed and twin bed with trundle with full bathbr(4.5 bathrooms total)brbr Extras You’ll Love:br• Garbage removal service (no trash hauling!)br• Washer & dryer br• Plenty of parking brbrAdventure Awaits: Step right onto the yellow-blazed trail that connects to the Old Appalachian Trail. Stunning overlook 1/5 mile from the house. brbrBook your stay and enjoy mountain views, outdoor adventure, and indoor fun for everyone.
Bed 5

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Bath 4

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Sleep 14

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Exceptional(17)

$391.08

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Private Vacation Home

Hickory Hideaway- 5 BR 4 BA with game room and indoor fire place

Wintergreen Resort, Virginia, United States

Welcome to the Hickory Hideaway! This 5 BR, 4 BA home is located in the heart of Wintergreen Resort. The home features a wood burning indoor fire place, 2 main level master suites, and a fully stocked kitchen. Downstairs you will find an additional gathering area and game room featuring a pool table, dart board, bar, card table and an assortment of games. All TVs (Living Room, Game Room & 2 Master BRs) are equipped with Youtube TV and Roku for all streaming services. Washer/Dryer and Wi-Fi are included. With 5 bedrooms and a loft, this home sleeps up to 12.brbrDue to the steepness of the staircase to the loft area, we request that the loft is only used by individuals 12+ years of age.brbrTo ensure the security of our guests, there is one security camera located on the exterior of the home. brbrAs a first responder family, we are honored to extend a 5% discount on the nightly rental rate to all Fire/EMS, Police, Healthcare workers, and Teachers. To obtain discount, please send us a message with proof of employment prior and requested dates prior to booking.
Bed 5

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Bath 4

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Sleep 12

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$342.4

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Private Vacation Home

Spacious + Serene Mtn Top Escape, 4 En Suites

Wintergreen Resort, Virginia, United States

Welcome to our mountain top home, just minutes from the heart of the resort, connected to walking trails, and with spectacular views. Our home is ideal for families, getaways, exploring the brew and wine scene, and hiking and skiing.brbrEnter this recently renovated home and discover an open floor plan on the main level with endless views of Shenandoah Valley. brbrHighlights include:brbr⊹ Spectacular Mountain Top viewsbr⊹ Every bedroom has an en suite bath!br⊹ Helix Hospitality Mattressesbr⊹ Cozy wood-burning fireplacebr⊹ Three Roku TVsbr⊹ Recently Renovatedbr⊹ Private parkingbr⊹ Large lockable ski lockerbrbrBring the family or a large group and enjoy the common space for gathering and another 3 floors of bedrooms to spread out and enjoy privacy.brbrWhen you come in the front door you will immediately experience the updated coziness and attention to detail in this home.brbrMAIN LEVELbrbrThe Main Level features an open floor plan kitchen, dining, living space, and a half bath. The dining has seating for 8+ with additional bar seating for 5. The kitchen is well-equipped with updated finishes and all of the cookware/appliances you could need for a home-cooked meal. All of the basic necessities are provided- coffee, creamer, sugar, olive oil, salt & pepper. The living room boasts vaulted ceilings, wall-to-wall mountain views, a wood-burning fireplace (please bring your own firewood), and access to the scenic deck. The Roku TV has all of the standard apps- just bring your own login. There is a custom-made, detailed GuideBook that provides information about both the house and activities, food, wine, beer, hiking, etc in the local area. brbrBEDROOMSbrbrThere are 4 bedrooms, each with its own updated private full bath. brbr⊹Bedroom 1 (top floor) features a queen bed and a 3/4 bathroom.br⊹Master Bedroom (middle floor) features a king bed, a full bathroom with a double vanity, a walk-in closet, and a private deck with mountain views.br⊹Bedroom 3 (middle floor) features a queen bed and a private bathroombr⊹Bedroom 4 (bottom floor) features a queen bed, twin bunk beds, and a private br bathroom.br⊹All 4 en suite bathrooms have a hair dryer. br⊹A pack-n-play with sheets is available for use. brbrOUTDOOR SPACEbrbrA short 100 yard walk right up the hill from the home is a private community picnic area with gorgeous views of the mountains and valley. Enjoy an unforgettable mountain sunset as you relax and play bocci ball and corn hole.brYou will also have access to the outdoor Chestnut Springs and Rhodes Farms pools located nearby (Memorial Day through Labor Day)brbrTRIP GUIDEBOOKbrbrWe created a custom 34 page Trip Guidebook for our home that we will email to you a couple of days prior to check-in. A hard copy is also available in the home. Features include:brbr✔ Information about the house for check-in/out and during your staybr✔ Details about Wintergreenbr✔ Information about area food, breweries, wineries, cideries, and distilleriesbr✔ Ideas for things to do with kidsbr✔ Ideas for activities and day tripsbr✔ Our favorite hiking trails both in and around WintergreenbrbrATTENTION TO DETAILbrbr✔ We provide high-end and health-conscious Public Goods brand shampoo, conditioner, body wash, hand soap, and lotion.brbr✔ Our home has a washer and dryer, along with an ironing board and iron for your use.brbr✔ We keep a first aid kit in the kitchen for minor cuts and scrapes.brbr✔ The living room, master bedroom, and downstairs kid bedroom feature Roku TVs, just bring your own login and enjoy any standard app.brbr✔ We provide premium linens for each guest.brbr✔ We provide basic paper goods and consumables - paper towels, tissues, toilet paper, dishwasher tablets, dish soap, sponges.brbr✔ Coffee, creamer, sugar are included.
Bed 4

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Bath 3

Bath

Sleep 10

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Exceptional(4)

$499.15

/ Nightly
Private Vacation Home

The Honey Den - Your Family's Spring Retreat

Wintergreen Resort, Virginia, United States

Welcome to The Honey Den - a warm 5BR, 4.5BA mountain home designed for slow mornings, golden-hour decks, and easy together time. Set among the trees, you get a dramatic double-height great room with a wood-burning fireplace, two levels of outdoor living including a hot tub and fire-table lounge, and flexible sleeping for families with two kid-friendly rooms downstairs. Slide open the doors to dine outside with a view, then wind down by the hearth after a day on the slopes or trails.brbrAt-a-Glancebrbr✓ ALL-YEAR FUNbr✓ HOT TUB + FIRE-TABLE LOUNGE (lower deck)br✓ DOUBLE HEIGHT LIVING/DININGbr✓ WOOD BURNING FIREPLACEbr✓ OPEN PLAN with sliders to decksbr✓ OUTDOOR DINING, HAMMOCK, BBQ GRILLbr✓ ENTERTAINMENT ROOMbr✓ HIGH-SPEED FIBER WIFIbr✓ NESPRESSO + DRIP COFFEE STARTER SETbr✓ DOG FRIENDLY (see Policies)brbr✓ 5 BEDROOMS • 8 BEDS • SLEEPS 11br✓ 4 FULL BATHS • 1 HALF BATH brbrbr★ FIRST FLOOR OVERVIEW ★brbr[ENTRY + POWDER]br✓ Step-in entry from boardwalk stairwaybr✓ Half bath and coat closet near the front door for easy access brbr[LIVING ROOM]br✓ Double-height vaulted wood ceiling, treetop viewsbr✓ Floor-to-ceiling stone wood-burning fireplacebr✓ Smart TVbr✓ Sliders to main deck for seamless indoor-outdoor flowbr✓ Après-ski ready: cocoa, a fire, and a movie night within steps brbr[OPEN KITCHEN + DINING]br✓ Fully equipped kitchenbr✓ Dining table with overflow table availablebr✓ Nespresso + drip coffee starter setbr✓ Easy pass-through to outdoor dining brbr[MAIN DECK: EXTERIOR LIVING]br✓ Outdoor dining with a viewbr✓ Hammock for afternoon readsbr✓ BBQ grillbr✓ Sunset-friendly seating areas brbr[PRIMARY FIRST-FLOOR BEDROOM w/ ENSUITE]br✓ Queen bedbr✓ Ensuite full bath with tub/shower combobr✓ Quality linens and bedside charging brbr★ SECOND FLOOR OVERVIEW ★ brbr[KING BEDROOM]br✓ King bed with vaulted ceilingbr✓ Dedicated sit/stand work deskbr✓ Quality linens and bedside charging brbr[QUEEN BEDROOM w/ENSUITE ACCESS]br✓ Queen bed with vaulted ceilingbr✓ Calming treetop outlookbr✓ Quality linens and bedside charging brbr[HALL BATH]br✓ Tub/shower combobr✓ Well-lit vanitybr✓ Fresh towels and bath essentials br✓ Ensuite access to Queen Bedroom brbrbr★ LOWER LEVEL OVERVIEW ★ brbr[ENTERTAINMENT ROOM]br✓ Flexible lounge set-up for games and movie timebr✓ Smart TVbr✓ Foosball Tablebrbr[LOWER DECK: HOT TUB + FIRE-TABLE LOUNGE]br✓ Plush sectional around a fire tablebr✓ Soak under the stars in the hot tubbr✓ Second outdoor zone separate from dining deck abovebrbr[LAUNDRY ROOM]br✓ Full size side-by-side washer and dryerbrbr[CHILDREN’S ROOM 1]br✓ Three twin beds (one as an upper bunk)br✓ Space to spread out toys and gearbr✓ Dedicated Hall Bathbrbr[LOWER HALL BATH]br✓ Convenient to bunk area and loungebr✓ Tub/shower combo br✓ Fresh towels and bath essentials brbr[CHILDREN’S ROOM 2 “GIRLS ROOM” w/ ENSUITE]br✓ Two twin bedsbr✓ Ensuite full bath adjacent with tub/shower combobr✓ Closet and nightstand storage brbrbrNearby Highlightsbrbr★PANORAMIC PURSUITS★brFounders Vision Overlook - (6 minute drive, 2 miles)brDevil’s Knob Overlook - (7 minute drive, 2.5 miles)brRaven’s Roost Overlook - (19 minute drive, 9 miles)br20-Minute Cliff Overlook - (22 minute drive, 11.6 miles)brbr★UNCORK AND UNWIND★brVeritas Vineyards - (26 minutes, 18.3 miles)*brHazy Mountain - (27 minutes, 19.6 miles)*brCardinal Point - (24 minutes, 16.7 miles)*brFlying Fox - (23 minutes, 16.8 miles)*br12 Ridges - (22 minutes, 12.9 miles)*brbr★HOP TO IT★brBlue Toad Hard Cider - (8 minutes, 4.6 miles)*brBold Rock - (9 minutes, 5.9 miles)*brDevil’s Backbone Basecamp - (14 minutes, 7.6 miles)*brThree Notch’d Brewery - (16 minutes, 10 miles)*brBlue Mountain Brewery - (29 minutes, 20.5 miles)*brbr★STEP INTO NATURE★brUpper Shamokin Falls and Morgan’s Loop - (9 min drive, 3.1 miles)brThree Ridges/A.T. Trail - (14 min drive, 6.2 miles)brWhite Rock Falls Loop - (21 min drive, 11 miles)brCrabtree Falls - (39 min drive, 21.9 miles)brbr★TEE TIME TRIUMPH★brStoney Creek Golf Course (25 minutes, 13.7 miles)brSwannanoa Golf Course and Country Club (26 minutes, 16.2 miles)brOld Trail Golf Club (30+ minutes in Crozet)brbr(All distances listed are from the WTG Entrance) brbrbr★ POLICIES / HOUSE RULES ★brNo Parties or EventsbrNo Smoking (inside or outside)brBooking Guest Age Minimum: 25brOccupancy per booking details. No additional overnight guests without prior approval.brLocal laws and ordinances apply.brQuiet Hours: 10:00 PM to 8:00 AMbrCleanliness: shoes off inside; no food or drink in bedrooms.brRespect Nature: no littering or wildlife disturbance.brbrPets (Dog-Friendly Home): up to 2 dogs under 50 lb each permitted with a one-time $50 pet fee per week. Notify in advance. Dogs not to be left alone unless crated. No dogs on beds. Registered service animals accommodated with notice. Guest is responsible for cleanup and any damages.brbrSecurity Camera Note: a Blink doorbell device may be present at the front entry, outward-facing only, motion-activated. No interior recording.brbrBreaking rules may result in termination of the stay with no refund. Guests without prior reviews may be asked to complete third-party verification via Truvi for a $30 fee. Thank you for helping us keep The Honey Den restful for everyone.
Bed 5

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Bath 5

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Sleep 11

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Exceptional(5)

$572.73

/ Nightly
Private Vacation Home

Spacious Mountain Family Retreat-Hot Tub & Game Room

Wintergreen Resort, Virginia, United States

Welcome to this spacious 5 bedroom 3 bath home located in the heart of Wintergreen, less than a mile from skiing and close to tons of area hiking, wineries and breweries. The home has everything you need for you and your kids and comfortably sleeps 14. Come enjoy the huge game room, hot tub and the large outdoor deck with seating, a grill and a fire pit.brDogs Welcome!
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Bath 3

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Sleep 14

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Exceptional(7)

$567.45

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Private Vacation Home

Hilltop Hideaway - Wintergreen 5BR with Hot Tub

Wintergreen Resort, Virginia, United States

Welcome to Hilltop Hideaway! Located in the heart of Wintergreen, Hilltop Hideaway features a hot tub, 2 propane firepits with seating, and covered outdoor dining. Inside, you'll love the soaring ceiling with a light-drenched open concept living room / dining / kitchen, plus a separate living room / game room downstairs. With 5 bedrooms, the house sleeps 12 comfortably. Zero steps to enter the home. Plus, pet friendly! Managed by Chris at New School Hosting.brbrHilltop Hideaway is located in the heart of beautiful Wintergreen in Virginia, which has tons to do for all ages, year-round. We are just a few minutes’ drive to the slopes and all the dining and entertainment at Wintergreen. Some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the home), plus there are other great trails just down the street. Also nearby are two sandy-beach-entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries- all within a 30 minute drive.brbrThe house has 5 bedrooms and 3 bathrooms, with the layout as follows:brbrMain level (note: zero steps required to enter home from driveway):brbr- Main level deck features covered dining for 6, propane firepit with 4 adirondack chairs, and gas grill (propane provided for firepit and grill)br- Living room with wood-burning fireplace (wood provided) and big screen smart TVbr- Dining area for 8, plus room for 4 more at the kitchen barbr- Fully stocked kitchen with brand new counters, stainless appliances, island with bar seatingbr- BR1: King bedroom with workspace area and bathroom accessbr- Full bath with dual entry (BR1 and hallway)- double vanity and shower/tub combobr- Laundry room with washer / dryerbrbrUpper level:brbr- Loft area overlooking living room with deskbr- BR2: King bedroom with workspace areabr- BR3: Small bedroom with sofa bed and smart TVbr- Full hall bath with showerbrbrLower level:brbr- Lower level deck features hot tub and propane firepit with seating for 8br- Additional living room / game room with pool table, shuffleboard, arcade machine, large smart TV, and multiple seating areasbr- BR4: Queen bedroombr- BR5: Bunk bedroom with twin-over-full bunk bed plus twin-over-twin bunk bed, and smart TVbr- Full hall bath with shower/tub combobr- Laundry room with full size washer and dryerbrbrOther things to note:brbr- Hilltop Hideaway is pet friendly! We allow up to 2 dogs with a $100 pet fee (total, not per pet or per night).br- Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.br- The driveway can easily fit 5-6 vehicles. There is an overflow parking lot nearby if needed.br- Wifi is fast with a strong signal throughout the house and decks.br- The living room, downstairs living room/game room, and 2 of the bedrooms have smart TVs where you can access whatever streaming services you subscribe to. We do not subscribe to cable.br- We provide a fully stocked coffee bar with multiple coffee drip and Keurig optionsbr- Linens and towels providedbr- Guests can enjoy free community pool access in the summer season (though the HOA rules stipulate no more than 6 guests at a time, and the permitted hours are 2-6pm).br- Pack n play, high chair, and kid dishes providedbr- We do require a separate rental agreement, which we will send a link to e-sign after you book. There are no additional fees beyond those listed here.
Bed 5

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Bath 3

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Sleep 12

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Exceptional(9)

$547.71

/ Nightly
Private Vacation Home

Wintergreen Resort Retreat: Ski, Hike, Golf!

Wintergreen Resort, Virginia, United States

From skiing at Wintergreen Resort to hiking the Appalachian Trail, this 4-bedroom, 3-bath house is perfect in any season. The vacation rental features at-home comforts, including furnished multi-level decks, a wood-burning fireplace, Smart TVs, and a fully stocked kitchen. Enjoy a round of golf, a scenic drive on the Blue Ridge Parkway, or grab a drink at a local brewery. Between your outdoor adventures, unwind with a family cookout and an al fresco meal surrounded by the mountain vistas.brbr-- THE PROPERTY --brbrPool Access | Outdoor Dining | In-Unit Washer & Dryer | Free WiFibrbrCreate new family traditions at this charming Wintergreen Resort home, perfect for ski vacations, leaf-peeping adventures, and golf getaways in the mountains.brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin BedsbrbrOUTDOOR LIVING: Furnished multi-level decks, gas grill, mountain viewsbrINDOOR LIVING: 3 Smart TVs, wood-burning fireplace, jetted tub, dining table, ceiling fans, board gamesbrKITCHEN: Fully equipped, cooking basics, dishware & flatware, drip & Keurig coffee makers, toaster oven, blender, knife set, breakfast bar w/ seatingbrGENERAL: Central heat & A/C, laundry detergent, linens & towels, complimentary toiletries, keyless entry, hair dryers, iron & boardbrFAQ: 5 exterior stairs required to enter, bedroom & bathroom on main level, 3 exterior security cameras (facing out)brPARKING: Gravel driveway (3 vehicles)brbr-- THE LOCATION --brbrWINTERGREEN RESORT ( 2 miles): Skiing, tubing, fishing, boating, hiking, golfing, mountain bikingbrOUTDOOR RECREATION: Three Ridges Hike (2.8 miles), Three Ridges Overlook (3.4 miles), Upper Shamokin Falls Trail (4.8 miles), Cedar Cliffs/Appalachian Trail (6.6 miles), Humpback Rock (16.0 miles), Blue Ridge Parkway (16.4 miles)brHIT THE LINKS: Devils Knob Golf Course (2.8 miles), Stoney Creek Golf Course (12.6 miles), Swannanoa Golf Course and Country Club (14.8 miles), Orchard Creek Golf Course (16.6 miles), Old Trail Golf Club (27.7 miles)brVINEYARDS: Caihailian Vineyard (5.9 miles), 12 Ridges Vineyard (14.1 miles), Valley Road Vineyards (19.9 miles), Afton Mountain Vineyards (20.4 miles), Lovingston Winery (24.2 miles), Mountain Cove Vineyards (26.9 miles), Ankida Ridge Vineyards (33.9 miles)brBREWERIES: Devils Backbone Basecamp Brewpub (6.5 miles), Wild Wolf Brewing Company (9.0 miles), Brewing Tree Beer Co. (15.8 miles), WildManDan Brewery (17.1 miles), Blue Mountain Brewery (19.5 miles)brAIRPORT: Charlottesville - Albemarle Airport (47.0 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smoking br- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: While there is a bedroom and bathroom on the main level, the property requires 5 exterior stairs to enter and may be difficult for guests with limited mobilitybr- NOTE: Your safety matters. This property features 3 exterior security cameras: 1 camera is located at the front door and faces the entryway, and cameras 2 and 3 are located on the back of the house facing the back entrances. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion. They will record when they first sense motion and 30 seconds after the last motion is detected
Bed 4

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Bath 3

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Sleep 8

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$255.3

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Private Vacation Home

Designer Look: Mountain View Pool Tennis One Level

Wintergreen Resort, Virginia, United States

SINGLE LEVEL home, no steps. Our contemporary mountain homestead sits amidst aboral oasis with mountain views. Work remotely w/ FAST Wi-Fi and unwind on the deck. Close to wineries, breweries, farmers markets, hiking and Upper Shamokin Falls trail.brbrComfortably sleeps 10: Queen, Queen, Bunk bed (single/double), and Bunk bed (single/double).brbrHappy pet fee $150. Seasonal outdoor pool/tennis access included.brbr2min to ski slopes!
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Bath 1

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Sleep 10

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Exceptional(9)

$896.2

/ Nightly
Private Vacation Home

Family Fun + Wellness • Hot Tub, Massage Chair, Sauna, 4 Outdoor Areas, GameRoom

Wintergreen Resort, Virginia, United States

Escape to Chateau Greenstone, the Wintergreen retreat where wellness & family fun shine. Something for EVERYONE: adults unwind in the Zen Den mini-spa w/ massage chair, red-light therapy, hot tub, sauna, fire pit & Vista Balcony. Plus Spiral Slide! 3 game areas (shuffleboard, bumper pool, ping pong, foosball, darts, pinball, arcade, kids’ cubby) plus heated outdoor TV/game lounge. 4 outdoor areas (2 covered), 9 huge TVs! Expansive view Nov-April, filtered mountain view May-Oct. Sleeps 18 cozily!brbrThe Propertybrbr...absolutely AMAZING! We've stayed at quite a few Airbnbs around the world, we've never seen anything like this. Your attention to every single detail is recognized in every corner of the house. - Schneur W.brbr• This welcoming abode will immediately start to nurture your need for both fun and serenity. All new modern furniture and amenities. brbr• Decorated in rustic and mid-century styling, with an added twist of funky/fun. Dramatic front window wall with lovely views beyond. with the screen room and the peaceful mini-spa. brbr• Top it off with unique views on the intimate for morning coffee, afternoon iced tea, or an evening nightcap. Breathe easy knowing that the younger ones are happy and occupied with loads of games, books, outdoor activities, and special areas just for them. Let your sojourn set its own path.brbr Designated beds & bedrooms for all - no messy, uncomfortable sleeper sofas, air mattresses, or open lofts.brbr 4 full bathrooms, including 2 true en-suite bathrooms + 1 dual-access en-suite bathroom.brbr Abundance of child/baby accessories - Pack n play, highchair, chair insert, tableware, potty seat, baby monitor, baby bath, extra bunk rail guard, outlet covers, and baby gates.brbrProperty Layout:brbr•• ••br▶ Great room with easy starting gas fireplace, high ceiling, and a bright and airy feel. 75” Smart TVbr▶ Dining room with table for 10, primary bar for 4, and secondary bar for 3 in living room for memorable group mealsbr▶ Kitchen with gas range, heavily stocked with virtually every accessory you’ll need for quick bites or large feastsbr▶ Coffee bar with combo Nespresso & K-pod machine, drip machine, French press, all needed accessories, charcuterie, plus unlimited ground coffee (decaf & regular,) and a healthy starter supply of numerous coffee pod, teas, hot chocolate & ciderbr▶ BR1: Primary bedroom, king bed, additional seating, large Smart TV, and ensuite bath with showerbr▶ BR2: King bed, large Smart TVbr▶ Main bath: full bath in hallbr▶ Laundry: centrally locatedbr▶ Front Deck (1st outdoor living area) with dining for 10 and bar for 2, several sofas and chairs around gas fire pit. Stainless BBQ, stainless pizza oven and utility cartbr▶ Covered & screened dining and game lounge (2nd outdoor living area) with dining for 4, plus 4 swivel conversation chairs, shuffleboard, mid-sized ping-pong, 75 Smart TV, and two commercial grade heatersbrbr•• ••br▶ BR3: Bunk room with 2 twin over full bunks, foosball, safe darts, arcade game, and kids’ cubby loaded with fun and kids’ sofa. Huge Smart TV with Xbox gaming console. Ensuite full bathroombr▶ Vista Balcony (3rd outdoor living area) has intimate bar seating for 4 with unique, distant viewsbrbr•• ••br▶ BR4: Two queen beds, vignette seating, in-room laptop-friendly workspace, huge Smart TVbr▶ Combo Game room / Theater room with massive 85” Smart TV, versatile bumper pool/card table, arcade game, pinball, large variety of board & group games (seniors, adults & kids), and mini fridgebr▶ BR5: King bed and large Smart TVbr▶ BR6: Adult friendly Queen bunks, love seat, and large Smart TVbr▶ Covered patio (4th outdoor living area) with covered hot tub for all-weather usage, 4-person sauna, various seating optionsbr▶ Zen Den mini-spa with massage chair, red-light therapy, electric fireplace, and water featurebr▶ Lower bath: bath with shower and dual access en-suite from hall or BR6brbr & br▶ 5 min walk (3 min drive) to the slopes (Tyro)br▶ 3 min walk to hiking br▶ 20 min drive to sandy beach lakes br▶ Numerous great dining options, golf, skiing, snowboarding, snow tubing, swimming, and Adventure Center (seasonal) within the resort complexbr▶ Wineries, breweries, distilleries, farmer markets, & bakeries within a 30 min drivebr▶ Renowned & inspiring Blue Ridge Parkway within 15 minutesbr▶ Close to everyone’s favorite activities for all 4 seasons brbr br▶ Guests have access to the entire home with a keyless entry codebr▶ Good comparative privacybr▶ Paved parking for 5-9 carsbrbr br▶ 2 Complimentary pools (HOA rules stipulate no more than 6 guests at a time, permitted hours are 2-6pm, Memorial Day-Labor Day)br▶ Wi-Fi – high speed, reliable, and strong connectionbr▶ Stocked essential spices, oils, spare bags, in kitchenbr▶ Linens & towels providedbr▶ Pack n play, highchair, chair insert, tableware, potty seat, baby monitor, baby bath, extra bunk rail guard, outlet covers, and baby gatesbr▶ Several outdoor gamesbr▶ Folding chairs available if neededbr▶ Level 2 EV charger (220v, 50A, 30ft charger – bring your adapter for Tesla) brbr br▶ Quiet hours 10PM to 8AM. Please respect our neighbors – no refund if asked to vacate for loud or disrespectful behaviorbr▶ House is 3 stories with 2 internal staircases & 1 external entry staircase to main entrance. Ground level access from parking to first floorbr▶ Like many Wintergreen homes, driveway is steep. Plan accordingly if winter weather. AWD or 4WD helps, but drive is usually plowed and cleared of most snow and 2WD typically sufficesbr▶ No refunds due to bad weather or roadsbr▶ Please, no open fires, charcoal grills, candles, etc other than fire pit or BBQbr▶ This property is in the mountains, in a heavily wooded area. The occasional bug may find its way inside. Rest assured, the house has regular pest control service for your comfort br▶ Please be Bear Aware - no food or trash to be left outside or in vehiclesbr▶ Requires separate rental agreement and house rules to ensure a smooth and pleasant stay for all parties. An e-sign link is sent to you after booking. 24 hrs to sign before the reservation is cancelled. No additional fees than what is shown here, other than potential damage/violation fines noted in house rules. Government issued ID's required for all adult bookers.br▶ $500 security damage hold (hold only, not charged.) br▶ Travel insurance encouraged. Life happens, protect yourself so you can re-book with peace of mindbr▶ Please be aware that there are exterior security cameras in place for your safety, aimed away from house
Bed 6

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Bath 4

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Sleep 18

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Exceptional(3)

$935.4

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Private Vacation Home

Slopes @ Tyro

Wintergreen Resort, Virginia, United States

We have a spacious, slope side, 3 level home with a convenient ski out basement. The resort & its surrounding areas offer a wide variety of activities (hiking, golfing, swimming, skiing, breweries, etc.), sights, & views to meet each person's expectations of what their getaway should be. Whatever it is you may be looking for, it is sure to be nearby. So come! Relax, explore, get together or don't, just enjoy!brThe spacebrThere is a fully supplied kitchen. There are stairs going into house. One bedroom on main floor w/Queen. The king bed is upstairs, and 2 rooms downstairs each have a queen bed and a bunk bed. Please leave ski boots & skis in ski mud room downstairs.brOther things to notebrDuring the summer you have access to the Chestnut springs pool and Rhodes Farm pools.brbrAdditional rulesbrPlease don't leave trash out side due to bears. there is a trash dumpster at the top of the hill.
Bed 4

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Bath 3

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Sleep 12

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Exceptional(1)

$884.97

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Private Vacation Home

Our Mountain Getaway

Wintergreen Resort, Virginia, United States

Come make Our Mountain Getaway your own! This is a very private home surrounded by beautiful mountain views with lots of gathering space for all to enjoy. The resort & its surrounding areas offer a wide variety of activities (hiking, golfing, swimming, skiing, breweries, etc.), sights, & views to meet each person's expectations of what their getaway should be. Whatever it is you may be looking for, it is sure to be nearby. So come! Relax, explore, get together or don't, just enjoy!brThe spacebrWalking through the front door of your getaway you will find a beautiful large family room with a fire place, high ceilings, and lots of windows over looking the golf course. This room is open to the dining room with a table for seating for 10 and a bar with an additional four seats. The kitchen has up to date appliances and even features TWO dishwashers to help make clean up a little easier! You can head outside onto the porch from either the kitchen or living room to enjoy the view, the outdoor dinning table, or to use the grill . On the main floor you will also find a large laundry room, a half bathroom, and the master bedroom. This bedroom has beautiful large windows so you can enjoy the view from the privacy of the king size bed, and its bathroom features double sinks, a private toilet, and a shower that doubles as a steam room. Up stairs you will find three more bedrooms. The smaller one has two twin beds. Then two larger rooms that both have their own private bathroom and a queen size bed. Downstairs is another large family room with a pool table and plenty of seating. Here you can find the door to the lower porch and the large inviting hot tub. Downstairs you'll also find a second large laundry room and two more bedrooms, also each with their own private bathrooms and Queen beds.brGuest accessbrThis home is close to many historical attractions, including Thomas Jefferson's Monticello, the National Historical Park at Appomattox Court House, the US National Parks Services Appalachian Trail which runs thru Wintergreen, the Shenandoah National Park with Skyline Drive and the Blue Ridge Parkway. Experience the incredible music scene here in the mountains, including festivals like Lockn, Festy, and Hoopla.brOther things to notebrYou can go to the Wintergreen web site to book activities, full and half day camps for children or ask for the activities center to arrange for babysitting. The Chestnut springs pool is available after 2 for your use and Lake Monacan is available every day but Saturday, this day you could check out Sherando lake.brbrAdditional rulesbrPlease have all dishes clean, I can unload dishwasher . brStrip the sheets off used bedsbrTrash goes to dumpster in the parking lot below spa.brPlease no pets
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$435.67

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Private Vacation Home

Cliffs Edge-A Contemporary Mountain Home

Wintergreen Resort, Virginia, United States

An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.brThe spacebrFeatured in Southern Living magazine when originally constructed, this Contemporary Mountain Home has an open floorplan with high ceilings and large skylights. This amazingly engineered vacation home that will stun you with its spectacular mountain views! Has magnificent cliff views of Crawford's Knob Mountain and the 1400-acre conservation easement of the Wintergreen Nature Preserve. Situated in the treetops, this cantilevered home extends outward into nature with expansive decks and a living area perfect for entertaining. It also has a desk/table area with the best working views of mountains you'll ever experience. The shoji screens are designed to give the loft elegant privacy. This is truly a four-season home where you can enjoy vistas of the National Parks Service's Blue Ridge Parkway and watch the seasons change from spring to summer to the beautiful fall foliage of Autumn. In Winter, enjoy cozying up in front of the fireplace after a day of skiing and tubing. Explore everything Nelson County and Wintergreen has to offer from breweries, wineries, cideries, hiking, biking, swimming, skiing, snow tubing, antiquing, fishing, archery, tennis and golf. This home is close to many historical attractions, including Thomas Jefferson's Monticello, the National Historical Park at Appomattox Court House, the US National Park Service's Appalachian Trail which runs through Wintergreen, the Shenandoah National Park with Skyline Drive and the Blue Ridge Parkway, the most visited National Park in the US with 15.9 million visitors. Experience the incredible music scene here in the mountains, including festivals like Lockn', Festy, and Hoopla!brGuest accessbrParking is available in the driveway and up near the road in the grass areas. The fireplace is wood burning, and you'll find that starter logs and firewood are supplied. In the outside closet you can find a charcoal grill, grill utensils, and foil there for your use. Paper products, trash bags, and a coffee/tea setup are in the kitchen for your use, as well as condiments that can be found in the refrigerator. Linens and towels are provided as well as guest soap. Three TVs, two with integrated Netflix, Amazon, various Apps, and one with a DVD player that also includes Netflix are in the home.brNature Foundation Passes are located in the Guest Information Booklet. You can go to the Wintergreen web site to book day activities, full or half day camps for children or ask for the activities center to arrange for a babysitter.brOther things to notebrSmoking, Pets, & Parties/events are not allowed. Self-check-in and check-out is with a lockbox. Lockbox is located behind the wall on your right while standing at the front door. A maximum of six people are allowed to stay in the home. Telephone usage REQUIRES WIFI CALLING to be ENABLED on your cell phone. This home does NOT have a landline and cell service can be spotty on the mountain without WIFI calling.brbrThe fireplace is wood burning, and the flue is open when you pull the handle (pulled forward). The charcoal grill must be used on the gravel in the front of the house. Charcoal and lighter fluid are not provided. Please be sure to clean the grill and utensils after use. This house uses a grinder pump, a device common to many homes in mountain communities. Please refer to the House Rules below, to see instructions on how to maintain it properly. Move-out instructions can be found in The Guest Information Booklet in the home. In addition, detailed information about the house and the community can be found in the Booklet.brbr-A more detailed list of instructions and community regulations can be found under -Additional Rules.brbrAdditional rulesbr•Please no shoes in the house. There are trays provided by the front door for shoes.brbrPlease no more than 3 cars in driveway, if extras park at the Wintergarden spa . brbr•Please refrain from making noise after 11PM!brbr•Please leave skis, poles, and snowboards outside or in the outdoor closet. Boots are allowed inside in trays provided.brbr•Maximum number of people allowed on deck is 10. No one is allowed on deck with heavy snow. Children need supervision of an adult while on deck.brbr•Wintergreen HOA does NOT allow motorcycles on the mountain. They must be parked at the Visitor Check-in Building.brbr•Grinder pump information: Grinder pumps allow sewage to flow in mountain communities more easily. Please do not dispose of any paper products other than toilet paper in the toilets. Failure to follow these instructions can result in sewer backups. Personal product bags are located in each bathroom. A grinder pump monitor is located in the kitchen. If you notice the red light turning on , please call us immediately. More information can be found in The Guest Information Booklet In the home. brbrUpon departure, please start the dishwasher with all the dishes, make sure you have cleaned the grill & utensils if you have used them! Turn OFF the upstairs thermostats, turn the downstairs thermostat to 55 degrees in the winter & 82 degrees in the summer. Lock ALL windows & doors. Please remove all the trash to the dumpsters at the Wintergarden parking lot and leave Wintergreen and Nature Foundation guest passes in the Booklet. Please place the original key in the lockbox. brbrThank you very much, we hope you enjoy your stay.
Bed 3

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Bath 3

Bath

Sleep 6

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$306.52

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Private Vacation Home

Altitude Adjustment-It's Pumpkin Spice Time!

Wintergreen Resort, Virginia, United States

This is a newly renovated condo with new flooring and furniture . Great place to come and relax after a day of hiking, skiing or visiting the local award winning wineries, brewery's, or cidery's. Come enjoy a cozy evening by the fire with your family or friends.brbrAdditional rulesbrPlease run the dishwasher and I can put them away, strip the used beds just leave on the floor. brThank you Julie
Bed 2

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Bath 2

Bath

Sleep 5

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Exceptional(13)

$457.1

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Private Vacation Home

Bluebird Mountain Home: Dog Friendly, No Step Master

Wintergreen Resort, Virginia, United States

Bluebird Mountain Home is a beautifully decorated, thoughtfully designed, light filled, cozy house nestled among the trees on Wintergreen Resort. This home offers NO steps from the front drive to the main level master suite and an impressive main level Billiard room and screen porch. Your dog is welcome in our dog friendly home with our fenced dog run area, there is a $150 pet fee per stay for up to 2 dogs. Guests have access to the community pool which is a short walk from the house. Relax with tons of books, games, puzzles, or unwind by playing billiards or guitar.
Bed 4

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Bath 3

Bath

Sleep 8

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Exceptional(3)

$341.38

/ Nightly
Private Vacation Home

Unwind at Bear Pause, located right at Wintergreen Resort.

Wintergreen Resort, Virginia, United States

Bear Pause at Wintergreen Resort – Spacious Getaway for Family & Friends!brbrEscape to the mountains and unwind at Bear Pause, a spacious retreat located right at Wintergreen Resort. Whether you're here for skiing, snowboarding, hiking, or exploring local wineries and breweries, our home is the perfect place to relax and recharge. With plenty of room for family and friends, you’ll find everything you need for a memorable stay in the Blue Ridge Mountains.brbrThe SpacebrThis comfortable 5-bedroom home offers plenty of space for your group:brbrDownstairs:brMaster bedroom with a king-size bedbrBedroom with two twin bedsbrCozy bedroom with a full-size bed (ideal for a single adult or child)brFull bathroom + additional half bathbrUpstairs:brBedroom with a queen-size bed and loft areabrBedroom with a bunk bed, a twin bed, and a loft areabrFull bathroombrGuest AccessbrGuests have access to the entire home, making it easy to settle in and enjoy everything Wintergreen has to offer.brbrCome take a Pause at Bear Pause —your perfect mountain escape!brbrWinter Conditions Notice: During snow or ice events, AWD/4WD is strongly recommended. The driveway is steep and may be impassable for standard vehicles.
Bed 5

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Bath 2

Bath

Sleep 11

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Exceptional(14)

Select Dates for Price
Private Vacation Home

Spacious 5-bedroom house in a mountain hollow in Wintergreen Resort.

Wintergreen Resort, Virginia, United States

Your Wintergreen Resort adventure begins at this 5-bedroom house. With 1 king bed, 3 queen beds, and 4 twin beds, this property offers plenty of space for guests to relax and unwind. Whether you're looking to explore the area or simply relax in the comfort of this terrific property, we look forward to hosting you at our place.
Bed 5

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Bath 4

Bath

Sleep 12

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Exceptional(9)

$229.27

/ Nightly
Private Vacation Home

Walk to Ski Slopes: Wintergreen Resort ‘Treehouse’

Wintergreen Resort, Virginia, United States

Short Walk to Eagle’s Swoop | Furnished Deck w/ Mountain View | Fireside Relaxationbrbr‘Treehouse’ is an updated mountain cabin close to the heart of Wintergreen Resort. This cozy 3-bedroom, 2-bath vacation rental is a perfect all-season getaway. The home offers a full kitchen, wood-burning fireplace, and spacious deck with seasonal mountain and sunset views – a perfect spot to unwind. Come enjoy all that the area has to offer, with easy access to skiing, hiking, breweries, vineyards, and more!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 king bedbr- Bedroom 3 (Loft): 1 king bed, 1 twin bedbrbrOUTDOOR LIVINGbr- Furnished deck w/ gas grillbr- Seasonal mountain viewsbrbrINDOOR LIVINGbr- 2 Smart TVsbr- Fireplace (wood provided)br- 6-person dining tablebrbrKITCHENbr- Refrigerator, dishwasher, stove/oven, microwavebr- Cooking basics, dishware & flatwarebr- Dual drip/Keurig coffee makerbrbrGENERAL br- Free WiFibr- Ductless mini-split A/C & heat unitbr- Electric baseboard heatersbr- Washer & dryerbr- Linens/towels, complimentary toiletriesbrbrFAQbr- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- 2-story home, stairs required to enterbr- Bedrooms & bathrooms on 1st floorbrbrPARKINGbr- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- Centrally located near hiking trails & ski slopesbr- 3 miles to Ravens Roost Overlookbr- 8 miles to Sherando Lakebr- 28 miles to Frontier Culture Museumbr- 33 miles to Grand Cavernsbr- 48 miles to Charlottesville–Albemarle Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 2-story property requires stairs to enter. The bedrooms and full bathrooms are on the 1st floorbr- Your safety matters. This property features 1 Ring exterior security camera at the front door facing away from the home. It does not look into any interior spaces. The camera records video and sound when activated by motion
Bed 3

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Bath 2

Bath

Sleep 7

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Exceptional(9)

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Bath 4

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Sleep 16

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Exceptional(9)

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