Vacation Rentals By Owner In Nellysford, VA

Cozy 3BR country cottage near Nelson 151 with a private hot tub, fire pit, yard games, and inviting indoor spaces. Perfect for families, couples, or friends looking to relax after wine tasting or mountain adventures.

Nellysford, Virginia, United States

Welcome to Carter’s Cottage, a cozy 3-bedroom country retreat designed for relaxed getaways near Nelson 151. Enjoy comfortable living spaces, a bright kitchen with island seating, and a private backyard featuring a hot tub, fire pit with seating, and yard games. The home includes a king bedroom, queen bedroom, and a bunk room that sleeps four—ideal for families or small groups. Peaceful, private, and close to wineries, breweries, and mountain views.brbrYou'll be interacting via TEXT directly with the owners, but not in person unless needed.brbrThe neighborhood is quiet and just a short walk or drive to rural downtown.brbrClose to: Nelson 151 wineries, breweries, cideries, and scenic drivesbrbrGuests have full, private access to the entire home and yard.brbrEntry is easy and contactless via keypad.brbrCarter’s Cottage is a single-level home designed for easy living and relaxed group stays.brbrThe main living area features comfortable seating, streaming TV, and natural light, flowing seamlessly into the kitchen and dining space. The kitchen includes a large island with seating, updated appliances, and everything needed for cooking and gathering.brbrSleeping arrangements:brPrimary bedroom with king bed and streaming Smart TVbrQueen bedroom with comfortable furnishingsbrBunk room that sleeps four — perfect for kids or friendsbrbrThe home includes a full bathroom and a convenient layout that works well for families and small groups.brbrOutdoor living:brThe backyard is set up for enjoying time together:brPrivate hot tub for relaxing soaksbrFire pit with seating (firewood provided)brCornhole and yard gamesbrCountry front porch with seatingbrOpen lawn space for kids to play or groups to gatherbrbrThe property feels private and peaceful, with a true country atmosphere while still being close to local attractions.brbrThe property is easily accessible by car and contains three parking spaces.brbrAs a 1950s home, some of the floors have a light creak to them — we consider it part of the cottage’s charm, but wanted you to be aware.brbrOutdoor amenities include:brPrivate hot tubbrFire pit with seating (firewood provided)brYard games including cornholebrFront porch and backyard seating areasbrbrOther Things to Note:brNo pets or smoking permittedbrHot tub is available year-roundbrLocated in a quiet neighborhoodbrIntended for relaxed stays; events and parties are not permittedbrbrThis is a quiet, rural property intended for relaxed stays. While it’s perfect for gathering outdoors, quiet hours are respected, and the home is not suitable for parties or events.brbrCountry Living & Pest ControlbrbrCarter’s Cottage is located in the beautiful Virginia countryside. With fresh air and open space comes the occasional visit from local insects.brbrWe maintain a regular professional pest control schedule and take preventative measures year-round. While this significantly reduces activity, it’s not possible to eliminate every bug entirely, especially during warmer months.brbrA few sightings are a normal part of country living — and part of the charm of being surrounded by nature.

3

Bed

2

Bath

8

Sleeps

$1241.59

/ Nightly

Private Vacation Home

Brew Trail Retreat: Hot Tub, Scenic Mountain Views, Game Rooms, Pet&Kid Friendly

Nellysford, Virginia, United States

Welcome to your private mountain retreat in Nellysford, a spacious 6-bedroom, 4.5 bath escape designed for unforgettable group getaways, family reunions, ski trips, and celebration weekends along the famous Brew Trail, with sweeping views of the Blue Ridge Mountains from every bedroom.brbrPerfectly located for both adventure and relaxation, this home is ideal for large groups looking to stay close to Wintergreen Ski Resort, explore nearby breweries, distilleries, and wineries, or simply unwind in a private mountain setting nestled on over 2 acres of land.brbrDesigned to comfortably host up to 16 guests, the home features six bedrooms with king and queen beds, including a unique bunk setup ideal for families or group stays. The bedrooms offer stunning mountain views, creating a peaceful retreat no matter where you sleep.brbrMultiple bathrooms throughout the home include spa-inspired features such as heated floors, oversized showers, waterfall showerheads, and thoughtful amenities for both families and groups getting ready for a night out.brbrThe heart of the home is a fully stocked chef’s kitchen built for group meals, complete with everything needed to cook and serve large gatherings. A dedicated coffee and tea bar and breakfast nook make mornings easy and enjoyable.brbrSpacious dining and living areas bring everyone together with comfortable seating for up to 16 people, games, and sweeping mountain views, perfect for shared meals, celebration dinners, or relaxing after a day on the Brew Trail or ski slopes. High speed WiFi internet is found throughout the home.brbrThis home was designed for FUN, whether you're here with family, friends, or celebrating a special occasion:brbrPrivate movie theater with 85” screenbrTwo separate game rooms (one with a bar, one with a gym)brArcade games and multiple game tables (pool table, shuffleboard, fooseball, basketball)brEntertainment spaces for both relaxed nights and lively group gatheringsbrbrWhether it’s a family movie night or a bachelor/bachelorette weekend, there’s space for everyone.brbrStep outside to expansive multi-level decks overlooking the Blue Ridge Mountains. Enjoy:brLarge hot tub with mountain viewsbrExtra-large BBQ grillbrScreened-in porch for year-round comfortbrFire pit for evening gatheringsbrPing pong table and outdoor games (corn hole, jenga, connect 4, outdoor kids toys)brMultiple seating areas designed for large groups and plenty of seating for up to 16 peoplebrbrFrom morning coffee to sunset drinks, the mountain views are always the highlight.brbrPerfect For: brFamily reunions and multi-family trips, brBachelor & bachelorette weekendsbrBrew Trail brewery, winery, and distillery toursbrSki trips to Wintergreen ResortbrGroup getaways and celebrationsbrbrThis is a rare mountain property designed for large groups who want it all: space, entertainment, privacy, and unbeatable views. Whether you're here to relax with family or celebrate with friends, the home is built to bring people together without ever feeling crowded.

Bed

Bath

Sleeps

$222.73

/ Nightly

Private Vacation Home

Blue's Barn: Central to Wineries & Breweries

Nellysford, Virginia, United States

Blue's Barn is a one-of-a-kind spot located at Stoney Creek in Wintergreen at the base of the Blue Ridge Mountains. Just minutes from Nelson 151, we are located near many award winning wineries, breweries, cideries and distilleries. Plus the barn is just 20 mins to the entrance of Wintergreen Resort!! The recently renovated barn is located on a residential lot a features an open concept living and dining space with an upstairs lofted king bedroom and private ensuite.brbrDOWNSTAIRS:brbrDining Room: counter height dining table with 4 stools brbrLiving Room: queen sleeper sofa, two side chairs, smart TV, chess table brbrKitchen: kitchenette-style with fridge, electric cooktop, sink, microwave, toaster and coffee pot. Please note that there is not an oven or dishwasher and supplies are limited. brbrPowder Room: single vanity with toilet brbrbrUPSTAIRS:brbrBedroom: king bed, nightstands, couch, desk, smart TV, full-length mirror brbrBathroom: walk-in shower, single vanity, toilet, toiletries (shampoo, conditioner, body wash, hand soap and lotion provided)brbrNote: we do provide an additional mattress under the king bed that can be pulled out to accommodate an additional guestbrbrBACKYARD: woodburning fire pit (firewood provided!) with Adirondack chairs; patio with lounge chairs and table; gas heaters. 2 burner, propane grill.brbrYou may see the owners cat, Mack Daddy, during your stay. He is friendly, and well-cared for; please don't let him accompany you into the barn!brbrADDITIONAL NOTES:br- The barn is located on a steep driveway and may require 4 wheel drive during winter months.br- Guests also have access to the Wintergreen pool and tennis/pickleball courts.br- This property is DOG FRIENDLY with an additional $75 fee/stay. No cats, fines may apply.brDOWNSTAIRS:brbrDining Room: counter height dining table with 4 stools brbrLiving Room: queen sleeper sofa, two side chairs, smart TV, chess table brbrKitchen: kitchenette-style with fridge, electric cooktop, sink, microwave, toaster and coffee pot. Please note that there is not an oven or dishwasher and supplies are limited. brbrPowder Room: single vanity with toilet brbrUPSTAIRS:brbrBedroom: king bed, nightstands, couch, desk, smart TV, full-length mirror brbrBathroom: walk-in shower, single vanity, toilet, toiletries (shampoo, conditioner, body wash, hand soap and lotion provided)brbrNote: we do provide an additional mattress under the king bed that can be pulled out to accommodate an additional guestbrbrBACKYARD: woodburning fire pit (firewood provided!) with Adirondack chairs; patio with lounge chairs and table; gas heaters. 2 burner propane grill.brbrYou may see the owners cat, Mack Daddy, during your stay. He is friendly, and well-cared for; please don't let him accompany you into the barn!brbrADDITIONAL NOTES:br- The barn is located on a steep driveway and may require 4 wheel drive during winter months.br- Guests also have access to the Wintergreen pool and tennis/pickleball courts.br- This property is DOG FRIENDLY with an additional $75 fee/stay. No cats, fines may apply.

Bed

Bath

Sleeps

$560.45

/ Nightly

Chalet

Opulent Retreat Amidst Blue Ridge`s Serenity * Dog Friendly * Hot Tub

Nellysford, Virginia, United States

Welcome to Whiskey Ridge Retreat, a cozy mountain getaway located within minutes of the ski lodge at Wintergreen Resort. Capture all the beauty of Wintergreen`s 4 seasons, hike, sip, ski in Roseland, Virginia. brbrWintergreen is a year round resort with access to skiing, summer/winter tubing, hiking, mountain biking, fishing, boating and golfing. You will be just minutes away from Nelson151, the travel destination for VA wine, craft beer, hard cider, distilleries and outdoor hiking trails.brbrRelax and Recharge in the heart of the Blue Ridge Mountains in your spacious, family-friendly home.brbrThis mountain retreat is located on Devils Knob Golf Course, relax on the large backyard deck overlooking the 14th green. Take a short stroll out of your backyard to capture some of the most breathtaking east coast sunsets.brThe deck has a propane grill and fire pit for outdoor entertaining, a fun egg chair and comfy Adirondack chairs for your whole crew. Not to mention a new hot tub for the ultimate relaxation. brbrOur mountain retreat offers four bedrooms, three with king beds and the other having a full over full bunk bed.. Two of the bedrooms are masters with one on each level of the house. The other two bedrooms have a full bathroom right outside the door. The downstairs full bathroom has a handicap accessible shower and jetted bathtub.brbrThe kitchen is well stocked with all necessary appliances and cooking accessories, sharp knives, cast iron, dutch oven, crock pot, electric griddle and more. Enjoy your morning coffee or tea with Keurig coffee maker and coffee pods included. A kitchen island has been recently added to provide more counter space, storage and extra seating. Your feet will enjoy the radiant heated kitchen floors first thing in the morning! brbrThe downstairs living area has an open floor plan so all of our guests can interact. The dining table can seat up to 10 people and in our opinion is one of our favorite features of the home. The artic entry/heated mud room is the perfect area to drop your snow gear before entering the house, a boot and glove heater is provided as well to help your gear dry for the next session.brbrEnjoy the vaulted ceilings and fully functioning wood burning stone fireplace.brbrThe carriage house also features a living room with a 55` smart tv to stream all of your favorite programs. The living room has two chairs and a pullout sleeper sofa that has a queen bed. Also in the living area, there is a kitchenette with a refrigerator/freezer, air fryer/toaster and Keurig coffee maker. There is a dinette located between the living room and kitchenette for extra seating. There is a full bathroom located in the living area as well.brbrThe private bedroom has a queen bed with a trundle underneath for additional sleeping space. There is a closet and a dresser for storage as well.brbrI personally will not be available but our Property Manger is available for questions that you may have.brbrOur home has 7 Smart TV’s throughout that allow you to stream all of your favorite programs. All three living rooms have a tv and four of the bedrooms have one as well.brShould heavy snow occur, we will have the premises cleared in a timely manner. A snow shovel and ice melt are provided and located in the closet on the front porch should this be needed in the meantime. brbrAdditionally, the driveway has an incline as you enter, 6 cars can fit at the top and one additional parking space in front of the garage for 7 total . In the event of snow, we advise to move cars to the street until our management team can clear the driveway. Do not attempt to drive up or down the driveway in snow without 4 wheel drive.brbr* Wood burning fires are prohibited outdoors.br* No candles allowed indoors.br* No smoking or vaping allowed indoors.brbrMust be 25 years old to book!

Bed

Bath

Sleeps

$562.43

/ Nightly

Private Vacation Home

6-bedroom house in Nellysford with WiFi AC Skiing Tubing and Golf

Nellysford, Virginia, United States

Discover the beauty of Nellysford from this 6-bedroom house. Marvelous king and queen beds await you, ensuring a brilliant night's sleep. With amenities like WiFi, AC, and a washing machine, your stay will be perfect. Our place will help you feel at home while you're traveling in Nellysford.

Bed

Bath

Sleeps

$690.26

/ Nightly

Private Vacation Home

Pilotview Hollow - *NEW* Luxury Nelson Co Retreat

Nellysford, Virginia, United States

Pilotview Hollow is a stunning NEW home right off the iconic Nelson 151 Brew Trail. The three story house is located in Nellysford, Virginia surrounded by the Blue Ridge Mountains, award-wining wineries and located 30-mins to Charlottesville and Waynesboro. The house features ample living space, 5 bedrooms and 4.5 bathrooms. brbrbrFIRST FLOOR:brbrLIVING ROOM - large, open concept living space with ample seating, wood burning fireplace and smart TVbrbrDINING ROOM - dining space for 6 guestsbrbrKITCHEN - fully stocked kitchen with stove, fridge, microwave, dishwasher, wine fridge and custom range hood, Nespresso machine and coffee potbrbrLAUNDRY ROOM - washer and dryer available for guest use (laundry detergent provided)brbrPOWDER ROOM - half bathroom in hallwaybrbrBEDROOM 1 - king bed, two nightstands with lamps, dresser and lounge chairbrbrBATHROOM 1 - private ensuite with double sinks, walk-in shower, toilet and large walk-in closet brbrbrSECOND FLOOR:brbrBEDROOM 2 - twin bunk bedbrbrBEDROOM 3 - two full beds, nightstand with lamp, dresser, closet with hangers brbrBATHROOM 2 - shared hallway bath with single vanity, tub/shower combo, toilet brbrBEDROOM 4 - queen bed, nightstand with lamp, dresser, benchbrbrBATHROOM 3 - private ensuite with single vanity, walk-in shower, toiletbrbrbrBASEMENT:brbrLIVING ROOM 2 - living space with couch, two lounge chairs, smart TV, board games and small desk for WFH spacebrbrBEDROOM 5 - twin daybed with twin trundle, basketball hoops, Pac-Man video game console brbrBATHROOM 4 -shared hallway bath with single vanity, tub/shower combo, toilet brbrbrOUTDOOR:brbrDECK - outdoor dining space, outdoor sectional with coffee table, rocking chairs, outdoor cooler and NEW Blackstone grillbrbrFIRE PIT - wood burning fire pit with 4 Adirondack chairs brbrbrPlease note :brThe garage is NOT guest accessiblebrPilotview Hollow is a private getaway down a long gravel road that may be un-plowed in snowy conditions. AWD is recommended in the winter months.brNO pets, violations subject to fines.brFIRST FLOOR:brbrLIVING ROOM - large, open concept living space with ample seating, wood burning fireplace and smart TVbrbrDINING ROOM - dining space for 6 guestsbrbrKITCHEN - fully stocked kitchen with stove, fridge, microwave, dishwasher, wine fridge and custom range hood, Nespresso machine and coffee potbrbrLAUNDRY ROOM - washer and dryer available for guest use (laundry detergent provided)brbrPOWDER ROOM - half bathroom in hallwaybrbrBEDROOM 1 - king bed, two nightstands with lamps, dresser and lounge chairbrbrBATHROOM 1 - private ensuite with double sinks, walk-in shower, toilet and large walk-in closet brbrbrSECOND FLOOR:brbrBEDROOM 2 - twin bunk bedbrbrBEDROOM 3 - two full beds, nightstand with lamp, dresser, closet with hangers.brbrBATHROOM 2 - shared hallway bath with single vanity, tub/shower combo, toilet brbrBEDROOM 4 - queen bed, nightstand with lamp, dresser, benchbrbrBATHROOM 3 - private ensuite with single vanity, walk-in shower, toiletbrbrbrBASEMENT:brbrLIVING ROOM 2 - living space with couch, two lounge chairs, smart TV, board games and small desk for WFH spacebrbrBEDROOM 5 - twin daybed with twin trundle, basketball hoops, Pac-Man video game console brbrBATHROOM 4 -shared hallway bath with single vanity, tub/shower combo, toilet brbrbrOUTDOOR:brbrDECK - outdoor dining space, outdoor sectional with coffee table, rocking chairs and outdoor cooler brbrFIRE PIT - wood burning fire pit with 4 Adirondack chairs brbrbrPlease note :brThe garage is NOT guest accessiblebrPilotview Hollow is a private getaway down a long gravel road that may be un-plowed in snowy conditions. AWD is recommended in the winter months.brNO pets, violations subject to fines.

5

Bed

4

Bath

12

Sleeps

$248.64

/ Nightly

Hotel

Everett Estate | Suite 1

Nellysford, Virginia, United States

Welcome to the newly appointed Everett Estate: Where Modern Luxury Meets Historic Charm. Boasting picturesque mountain views, this 6,700 square ft home underwent a year-long renovation to modernize & revitalize both the home & the expansive grounds. brbrWith 10 all-suite rooms and 1 top floor studio apartment, this boutique inn was expertly designed to host up to 30 overnight guests and weddings and events of up to 125 guests. brbrInterior Design: Becky Seager | WKNDR Design of CharlottesvillebrbrbrYou may see our personable and helpful staff throughout the common areas of the estate during standard business hours of your stay to help keep it well maintained. There is a separate office on the interior of the home that remains locked when our staff is not onsite. There is another office area in a separate building that will sometimes be used by our crew, too. brbrbrbrLocated conveniently along Nelson 151 in Nelson County Virginia and the Blue Ridge Mountains! Nelson 151 is the travel destination for Virginia wine, craft beer, hard cider and outdoor recreation lovers. Route 151 is a designated Virginia scenic byway on the sunrise side of the Blue Ridge that connects the Nelson 151 member businesses.brbrSix wineries (Afton Mountain Vineyards, Cardinal Point Vineyard and Winery, Flying Fox Vineyard and Winery, Hill Top Berry Farm & Winery, Valley Road Vineyards and Veritas Vineyard), three breweries (Blue Mountain Brewery, Devils Backbone Brewing Company and Three Notch'd), and two cideries (Blue Toad Hard Cider and Bold Rock Hard Cider) decided to form a group to more efficiently market and leverage their unique “micro” appellation. Nelson 151 was created.brbrThe Nelson 151 members recognize and celebrate the benefits of their proximity to one another in the pastoral Rockfish Valley. With orchards and farms, unique shopping, bed and breakfasts, local restaurants, community theater, hiking, biking, skiing, golf, fresh air and unforgettable views: Nelson 151 is the perfect choice for a day trip or weekend excursion.brbrAll self check-in- guests will be provided with a unique code that opens the front door and the door to their suite.brbrUniquely designed guest rooms, modern amenities, and thoughtful touches await you at Everett Estate. This restored Inn delivers a boutique experience filled with plenty of dazzling details and alluring views and amenities to ensure an unforgettable stay. Enjoy pure relaxation as you take in the sweeping views of the Blue Ridge Mountains. Sip your morning coffee from one of our numerous intimate hideaways. Indulge in a cozy cocktail while you converse with friends by the fire pits. brbrThe Layout:brbrFirst Floor (Common Areas- shared by all guests)brbrParlor- Moody living area with purple walls and conversational seating. This room has a full bath with a stand-up shower available for all guests to use. There is also a separate ADA-compliant half bath located inside of the parlor.brbrDining Room- Four separate 4-seat dining tables are great for card games, cocktails or meals. brbrOriginal 110 high functional wood pocket doors separate the dining area from another living space, featuring 2 champagne velvet sofas, an additional 4-seat dining table for games or eating, and another half bath. brbrSuite 1: brLocated on the first floor. Stairs are not required.br-Sleeps 2br- Private smart lock entry through your own semi-private side porch or internal entry through a hallwaybr- Semi-private covered side porch (accessible by separate doors via both the Parlor and Suite 1) is the perfect place to enjoy morning coffee or evening winebr- Double door passage if you would like to combine it with Suite 2br- King Bedbr-SNOOZ sound machinebr-Private bath, walk-in showerbr- 50 Smart TVbr- Keurig with coffee and tea fixingsbr-Wine glasses, drinking glasses, and wine bottle openerbrbrPlease Note: In an effort to create a peaceful and relaxing environment for all of our guests, we welcome well-behaved children ages 12 years and above to join their parent or guardian in our suites. Children of all ages are welcome to stay when you rent the entire Estate. We apologize for any inconvenience. brbrDue to the nature of the property, guests are not allowed to bring their pets to stay.brbrbrbrThe property holds a rich history that traces back to its original owner, Dr. Charles Everett. This esteemed physician had the honor of serving as the personal physician for not just one, but three American Presidents: Jefferson, Madison, and Monroe. However, it was his close friendship with Thomas Jefferson that truly shaped the legacy of the estate. Together, they would venture from their separate residences in Charlottesville, Monticello, and the Belmont Tract to this very location, formerly known as Upland Manor.brbrWhile the property has changed hands multiple times throughout its history, its most recent iteration was as a thriving Bed and Breakfast called The Mark Addy Inn. Renowned for its exceptional accommodations and on-site restaurant, The Mark Addy Inn fostered a sense of community in Nelson County for countless years. However, under new ownership, the inn embarked upon a meticulous and respectful restoration process, both inside and out, culminating in an opulent boutique experience for by-the-night travelers and the ability to rent the whole estate for weddings and events. brbrThe rejuvenated design not only pays respect to a bygone era, but also reflects modern sensibilities by showcasing an array of vibrant and unique guest rooms, elegant common areas, and a complete revitalization of the surrounding grounds. These elements are masterfully intertwined through an enchanting color scheme and recurring patterns, ultimately creating an ambiance that captivates guests and transports them to an enchanting era of the past, with a contemporary twist. brbrDiscover the blend of modern hospitality and historic charm at Everett Estate—we can't wait to welcome you!

1

Bed

1

Bath

2

Sleeps

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