Vacation Rentals By Owner In Whitingham, VT

$175

Lake Whitingham & Mount Snow Area Village Apartment

Whitingham, Vermont, United States

Get Back to the Garden in Jacksonville Village in Whitingham at this enchanting garden apartment. The property is a 5 mile drive to Lake Whitingham, 10 minutes to Wilmington, and 25 minutes to Mount Snow. With 2 full beds in 2 bedrooms, guests can relax in comfort. Soak in the bathtub, listen to fountains in the garden, enjoy eclectic decorating with antiques, AC, WiFi, TVs, gas and electric fireplaces and an outside fire ring are also available. Walk to the general store, or grab pastries or sandwiches from the bakery have dinner or play at the local pub, Jax on Tap. Work or play - ski, kayak, swim, shop, antique, go to the theater - from your private apartment in the Village of Jacksonville.

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$302

/ Nightly

Private Vacation Home

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Whitingham, Vermont, United States

UP TO FOUR MORE ADDITIONAL GUESTS CAN CAMP ON THE LAKEFRONT PROPERTY. Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. brbrA perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. Our tiny home sits just steps from the shore with amazing views of the lake and the mountains. It's a quick drive to skiing at Mount Snow, shopping and dining in quaint WIlmington, and around the corner from the VAST trail. Enjoy a drink on the deck or a dip in the hot tub. End your day curled up on the leather couch in front of the fireplace.brbrThe tiny home has a spacious living room with views of the lake and the mountains. There is a fully equipped kitchen with refrigerator, stove, microwave, coffee maker, and toaster. The bathroom has a toilet, vessel sink, and rainhead shower with unique metal sides. The bedroom features a queen bed and a window seat with a direct view of Sadawga Lake.brbrThe lot is private and has 150 feet of lakefront with a dock. Take advantage of the beautiful, private deck and large hot tub that overlook the lake. We have a hammock to hang beneath the trees lakeside, or you can take out one of our kayaks to explore the beautiful floating island.brbrWe do allow pets at our tiny home and do not charge an extra fee for them. Because of the small size of the home, we request that pets are no larger than 50lbs. We also require guests to tell us that they are bringing a pet during the initial booking process.

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$206

/ Nightly

Private Vacation Home

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Whitingham, Vermont, United States

This very private 3 bedroom, 1 bath, getaway is off the beaten path nestled on 28 quite wooded acres that abut the Green Mountain State Forest This newly updated home is very open, bright & airy with all new appliances. Close to Sadawga Lake and the Harriman Reservoir for boating, swimming, fishing or just relaxing by the shore. The VAST snowmobile trails are around the corner and snow shoeing & hiking can be done right on the property. Mount Snow is a quick 25 minute ride. Berkshire East Mountain Resort is about 30 minutes away and offers 4 season fun as well. There are also loads of hiking areas in the vicinity. Relax on the deck or set up yard games by the firepit.

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Sleeps

$447

/ Nightly

Cabin

Lakefront House with Stunning Views and Great Room

Whitingham, Vermont, United States

This waterfront home on Sadawga Lake is the perfect family getaway or couples retreat. The spacious log style home has a wraparound deck to take in the incredible views. The home has a large open concept great room, a dining area, and kitchen. On the first floor, there are two pull out couches in the great room, full bath, and two bedrooms, each with a queen bed. The second floor has the primary suite with a king bed and vaulted ceilings, a second full bath, and loft with a pull out couch. The deck has a sectional sofa perfect to lounge on. There are two wooden lounge chairs to soak up the sun. The house has an unfinished basement with a brand new ping pong table. brbrThe property has a private boat dock and direct water access on Sadawga Lake for fishing, swimming, and boating in the summer. The boat dock is removed from September thru May, although there is still access to the lake for ice fishing. The fall foliage is also stunning. The property has nearly 360 degree views of the water and mountains, with sunrise views through the large windows facing the lake. There are two kayaks with paddles and life jackets that guests can use on Sadawga Lake at no additional cost. The property has a Weber propane grill, fire pit, and outdoor volleyball net to enjoy the outdoors. brbrThere are nearby hiking trails, golf courses, and direct VAST snowmobile access. The cabin is just a short drive from the Harriman Reservoir (~2 minutes away), Wilmington (~14 minutes away), Mount Snow ski resort (~25 minutes away), and Berkshire East ski resort (~28 minutes away). Harriman Reservoir, also known as Lake Whitingham, is the largest body of water located entirely within the state of Vermont and extends about 10 miles, with clear waters, picnic/beach spots, and boat launches. Historic downtown Wilmington offers shops and an array of restaurants.brbrThe three bedroom property includes 1 king bed, 2 queen beds, 3 queen size pull out couches, ping pong table, weber propane grill, stove, oven, fridge, microwave, Keurig coffee maker, iron, ironing board, panini press, toaster, rice cooker, slow cooker, colander, pots, pans, plates, glasses, wine glasses, dish washer, and utensils. The house has internet/Wifi. If you have questions about any other amenities that you need, please ask us so we can let you know if we have it.

5

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2

Bath

8

Sleeps

Select Dates for Price

Cabin

Cool Converted Cabin with strong wifi in Whitingham

Whitingham, Vermont, United States

Escape to this lovely recently converted cabin retreat situated on 12 acres in Whitingham. Enjoy the swimming hole with wooden dock and inner tubes for relaxing in the summer months. Enjoy hiking and snow shoeing in the winter. Watch the amazing stars while sitting next to the stone fire pit, or sit on the covered porch next to the house and gaze out over the lush landscape.brbrEnjoy the enchanting two story Living Space with double height garage door with screen that can be left open all day. Sit by the gas fireplace and enjoy a book or make a meal in the well equipped chef's kitchen. Relax in the bright Family Room with windows on three sides which features an extra large TV, wood burning stove and two sofa beds for extra guests. brbrCatch up on work in the upstairs loft area and stay connected with very dependable Star Link WiFi. Take advantage of the radiant floor heating on both levels for chilly nights. brbrUnwind in the two queen bedrooms upstairs, each offering a cozy atmosphere and beautiful views of the gorgeous hilly landscape. Relax in the spa-like corner bathroom, complete with a separate shower and massive bathtub. brbrMake yourself at home in this enjoyable getaway. We look forward to hosting you at our place.

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Sleeps

$881

/ Nightly

Private Vacation Home

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Whitingham, Vermont, United States

Experience your private slice of paradise in Vermont's scenic Green Mountains at this family vacation rental in Whitingham! Nestled on 13 wooded acres with a hot tub, multiple living areas, a fire pit, and a game room, this 5-bedroom, 4-bath home offers incredible spaces for you and your loved ones to spend quality time. Winter brings opportunities to hit the slopes at Mount Snow, Berkshire East Mountain, or other nearby resorts, while summer days are ideal for hiking and relaxing poolside.brbr-- THE PROPERTY --brbrMRT-11153470-001 | Private Pool | Fire Pit | Sledding & Snowshoeing On-Site | ~14 Miles to Berkshire East Mountain Resort | High Speed InternetbrbrIdeal for multigenerational families and outdoorsy groups, this peaceful property offers the perfect space for entertaining and creating lifelong memories.brbrBedroom 1: King Bed | Bedroom 2: King Bed, Twin Bunk Bed | Bedroom 3: Queen Bed, Twin Bunk Bed | Bedroom 4: Queen Bed, Twin Bunk Bed | Bedroom 5: Twin Bed | Additional Sleeping: Pack ‘n PlaybrbrOUTDOOR LIVING: Seasonal outdoor pool (mid June - end August, fenced, depth 3’ - 9’), seasonal pool house w/ full bathroom, spacious backyard, upper & lower decks, mountain views, hot tub, gas grillbrKITCHEN: Fully equipped, 2 full refrigerators, butcher block table, 6-burning professional gas range, cooking basics, spices, coffee maker, dishware/flatware, paper towels/trash bags, blender, toaster, toaster ovenbrINDOOR LIVING: Smart TV w/ Roku, 3 stone fireplaces (firewood provided), game room w/ pool table, ping pong & foosball, dining table, high chair, farmhouse style interiorbrGENERAL: Free WiFi (150 Mbps), linens/towels, complimentary toiletries, washer/dryer, hair dryer, iron/board, keyless entry, central A/C & heatingbrFAQ: 2 steps required to access, bedroom & bathroom on main floor, 2 exterior security cameras (facing out toward driveway & pool area), pet fee (paid pre-trip), 4WD recommended in winter & springbrPARKING: Garage (1 vehicle), driveway (10 vehicles), RV/trailer parking is allowed on-sitebrbr-- THE LOCATION --brbrWINTER RECREATION: VAST snowmobile trails (steps away), Berkshire East Mountain Resort (14.2 miles), Mount Snow Grand Summit Resort (17.0 miles), Prospect Mountain Ski Area (22.7 miles), Brattleboro Ski Hill (25.3 miles), Stratton Sun Bowl Base Lodge (30.9 miles), Bromley Mountain Ski Resort (44.2 miles)brGREAT OUTDOORS: Lake Sadawga (2.7 miles), Harriman Reservoir (5.5 miles), Molly Stark State Park (10.6 miles), Green Mountain Beach (10.9 miles), Hogback Mountain (12.9 miles), Mount Snow Golf Club (16.2 miles), Woodford State Park (19.4 miles), Green Mountain National Forest (20.6 miles), Natural Bridge State Park (23.9 miles), fishing, swimming, hiking, snowmobiling, golfingbrATTRACTIONS: Wilmington Antique and Flea Market (8.3 miles), The Art of Humor Gallery (10.3 miles), Southern Vermont Natural History Museum (11.9 miles), Creamery Covered Bridge (25.0 miles)brNEARBY TOWNS: Wilmington (9.4 miles), Dover (16.6 miles)brAIRPORT: Albany International Airport (69.7 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- This property has a strict maximum occupancy of 12 adultsbr- Must be at least 30 years old to bookbr- No smoking br- Pet friendly w/ $75 fee per stay (+ fees & taxes, dogs only, max 1)br- No events, parties, or large gatherings br- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: 4-wheel drive or all-wheel drive is necessary in the winter and spring months to access the propertybr- NOTE: Guests may utilize the attached garage to store skis, but the detached garage is not available for guest usebr- NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is located on the front of the house facing towards the driveway and camera 2 is on the back of the house facing towards the pool area to monitor the snow accumulation on the pool cover for safety. The cameras are outward facing and do not look into interior spaces. The cameras record video and audio when activated by motion

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$328

/ Nightly

Private Vacation Home

Cozy Southern Vermont Home w/ On-Site Trails

Whitingham, Vermont, United States

Treat yourself or a loved one this holiday season to a peaceful escape at this 2-bed, 1-bath vacation rental. If you're visiting in winter, spend the day shredding the slopes at Mount Snow, or build a fire and cozy up with a good book. If you're seeking more temperate days, wander the property's vast acreage and admire stunning foliage in the fall, and lush greenery in the summer. For a taste of what's local, visit a variety of sugar houses, apple orchards, and renowned New England restaurants.brbr-- THE PROPERTY --brbrMRT-11153470-001 | 70+ Acres | On-Site Hiking & Snowshoeing | 20 Mi to Mt. SnowbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed brbrHOME DETAILS: Flat-screen TV, wood-burning fireplace, dining tablebrOUTDOOR SCENERY: Covered porch w/ rocking chairs, back deck w/ forest view, wooded trailsbrKITCHEN: Cooking basics, stainless steel appliances, dishware & flatware, microwave, drip coffee makerbrGENERAL: Towels/linens, free Starlink WiFibrFAQ: Access only by stairs, exterior security cameras (2, facing out), no A/CbrPARKING: Driveway (4 vehicles), RV/trailer parkingbrbr-- THE LOCATION --brbrWINTER RECREATION: Cross-country skiing & snowshoeing (on-site), Berkshire East Mountain Resort (14 miles), Mount Snow Resort (19 miles), Prospect Mountain Ski Area (23 miles), Stratton Mountain Resort (32 miles)brSUMMER ADVENTURE: Hiking & birdwatching (on-site), Harriman Reservoir (5 miles), Mt. Olga Trailhead (10 miles), Hogback Mountain Conservation Area (11 miles), Mount Haystack Trail (13 miles), Mohawk Trail State Forest (16 miles), Natural Bridge State Park (24 miles)brALL-SEASON FUN: Downtown Wilmington (10 miles), Southern Vermont Natural History Museum (12 miles), Brattleboro Common (25 miles), Downtown Bennington Historic District (30 miles)brAIRPORT: Rutland Southern Vermont Regional Airport (73 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 gatherings br- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to accessbr- NOTE: The property does not have air conditioningbr- NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is located on the front porch facing out, and camera 2 is located on the side porch facing out. The cameras are outward facing and do not look into interior spaces. The cameras will record video only while guests are in residence

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$488

/ Nightly

Private Vacation Home

Lovely Contemporary Vermont Home

Whitingham, Vermont, United States

Welcome to Trail Haven! Whether you are a skier, snowmobiler or avid hiker - our lovely home is thebrperfect place to be for your Vermont escape. Set on three wooded acres we have access right from ourbrproperty to the VAST trails and are a quick 13 miles to Mt. Snow and not far from Bromley, Stratton andbrother mountains. If you’re staying in the summer and early fall we are 5 minutes away from one ofbrVermont’s premier lakes, Harriman Reservoir, where you can kayak, boat, fish or swim the stresses ofbrthe world away! Our location is ideally set on a paved road that gives you peace of mind in the Vermontbrweather and brings you right into fun town of Wilmington within minutes. The interior of our homebrevokes a modern farmhouse style that allows for comfort, coziness and convenience all in one. Threebrspacious bedrooms, three full baths and a loft with beds allow you and your guests to have privacy andbrcomfort during your stay. Our living room with soaring windows offers two couches and a comfy readingbrarea. The state-of-the-art fireplace provides all the ambiance you need to enjoy your perfect day whenbryou’re looking for a little downtime. There’s a nice choice of good old fashion games, puzzles and booksbrfor family fun and did we mention that we have three flat screen televisions for the movie, sports orbrgaming enthusiast We have a nice desk and chair in the loft to give you a quiet and comfortablebrworkspace if you need to get a little work done. The fully equipped kitchen has brand new stainlessbrappliances and a well-stocked kitchen with everything you need (including plenty of pots and pans) tobrfeed the crew or have a nice romantic dinner for two! If the adventures of the day keep you frombrcooking there is a nice variety of local restaurants in the area that are minutes away and will providebrdelicious food for your convenience. The walkout basement mudroom is great for easy unloading andbrloading of all your gear without schlepping it all through the house. Outside you will find a firepit circledbrby super comfy rocking chairs.brbrWhat’s nearby:brSnowmobile VAST Trails access on property – no need to trailer once you’re here! Mt. Snow is an easybr13 miles away, Stratton is 30 miles, Bromley is 40 miles. Cross County Trails at Mt. Snow and at ProspectbrMountain (19 miles). Hiking Trails nearby - Molly Stark State Park (7 miles) and Mt. Haystack (10 miles)brare popular. Harriman Reservoir kayak launch is 3 miles and boat launch and swimming are 9 milesbraway. The area boasts a number of beautiful golf courses including Mt. Snow Golf Course, Haystack GolfbrCourse and the Hermitage Club. Shops and restaurants in Wilmington (5 miles) and two country storesbr(pizza, coffee, yummy sandwiches) and a bakery in downtown Jacksonville just 2 miles down the road.brBreweries, distilleries, shops and other restaurants are also located in Dover and surrounding areas.brThings to know:brFree

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$748

/ Nightly

Private Vacation Home

Private Large Spacious Mt Snow Ski-Lake Home Vermont

Whitingham, Vermont, United States

Come relax with your family and friends at this private and centrally located home situated on Ryder Pond. 15 mins to Mt. Snow for skiing, 5 mins to Harriman Reservoir for kayaking, paddle-boarding and swimming. EV charger in garage.brbrTake a dip in our hot tub after a long day, watch the sunset from our beautiful deck, relax while surrounded by 20 acres of beautiful land. 7 min drive to downtown Wilmington for great dining, shopping and cafes. Try the local maple syrup/homemade ice cream and enjoy the outdoors!

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Select Dates for Price

Chalet

Secluded Mountain Chalet

Whitingham, Vermont, United States

*Mount Snow / Berkshire East / VAST*brbrThis spacious mountain chalet is a great space to share with your family or friends! brbrQuiet and secluded, the house is located on a wooded lot at the end of a private road at the top of the hill in Whitingham.brbrSuper fast Starlink WifibrbrMount Snow - 20 minbrBerkshire East/Thunder Mountain - 25 minbrStratton - 45 minbrDowntown Wilmington - 10 minbrLake Whitingham boat launch - 5 minbrRide to VAST trails 1/4mibrbrThe spacebrThis spacious mountain chalet was architect-designed and built in 1979. The main living space is on the upper level with an open plan, great for entertaining with family and friends! An expansive living room with vaulted ceilings, huge south facing windows, and a wood burning fireplace opens out to the large front deck. An open kitchen (fully equipped!) and dining area adjoin the living room.brbrThe main bedroom and one full bath are located on this level.brbrDownstairs is another private bedroom with queen bed, a second full bath, laundry, and a large family room with two bunk beds behind a room divider, and a pull out sofa in the living room area.

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$814

/ Nightly

Private Vacation Home

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham, Vermont, United States

An experience like no other... all for less than $47 a night per person! A perfect blend of historic charm and 21st century comforts. Our house is a unique Victorian Mansion set on 3 beautiful lakeside acres in southern VT. There’s room for everyone in your group to have their own space, along with common areas for friends and family to gather together for meals, talks, games, and fun. Our house is close to boating, fishing, skiing, snowboarding, hiking, and all that VT has to offer.brbrOur spacious home boasts 6 master bedroom suites with private full baths and 2 additional bedrooms with twin beds. Our kitchen is fully equipped with pots, pans, and utensils, for those big family dinners or late morning breakfasts. Have your meals together in the spacious dining room. There are three living areas: the Living Room, with TV and gas fireplace; the Lounge, a perfect space for drinks, games, and conversation; and the Family Room with a huge sectional and a 75” TV - perfect for family movie night. The house is well stocked with bedding, linens, and includes a washer and dryer, and has a heated mudroom with plenty of storage for ski gear and equipment.brbrThere are extensive grounds outside the house that include a patio, hot tub (with heated deck mats in the winter), and picnic table. Just steps away is Sadawga Lake, where you can fish, kayak, hike, ice skate, or sit near the waterfall and enjoy the sun. Less than a mile away is the Harriman Reservoir southern boat launch. There are so many nearby attractions, including skiing, snowboarding, snowmobiling (VAST trail down the street), hiking - not to mention numerous shops, restaurants, and breweries.

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$463

/ Nightly

Private Vacation Home

'John's Farmhouse in Mount Snow' on 120 Acres!

Whitingham, Vermont, United States

James Gandolfini from “The Sopranos” was a repeat guest at 'Mount Snow Farm,' a 120-acre former dairy farm nestled in the Green Mountains near Whitingham. This family-friendly property sits 2,300 feet above sea level, offering a view of the Harriman Reservoir in Wilmington. This 5-bedroom, 2-bath rustic vacation rental is reminiscent of days past, making it the perfect getaway to rest the soul and relax the mind! Mountain Snow Grand Resort is just 30 minutes away for 4 seasons of outdoor fun.brbr-- THE PROPERTY --brbr* Please go to YouTube and search JohnsFarmDrone+Music1 to view aerial footage of the property! *brbrMRT-11153470-001 | Views at 2,300 Feet | 120 Private Acres | Fire Pit | Fantastic Sunset & Mountain Views | Window & Standing Fans (All Rooms)brbrReserve this expansive, family-friendly property for your next White Mountain getaway for a unique experience that's sparked many repeat guests!brbrBedroom 1 (1st Floor): Full Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin Beds | Bedroom 4: 2 Twin Beds | Bedroom 5: Queen Bed | Additional Sleeping: Pack 'n PlaybrbrINDOOR LIVING: Flat-screen TV, deep wood paneling, entertainment system, wood-burning fireplace, hardwood floors, formal dining room w/ 8-person table, laptop-friendly workspace, board games, 1,900 sq ft brKITCHEN: Fully equipped, drip coffee maker, toaster, gas range, toaster oven, cooking basics, dishware & flatwarebrGENERAL: Free WiFi, washer & dryer, linens/towels, central heating, full-house generator, charcoal grill, suitable for children & elderlybrFAQ: Stairs to access, bedroom on 1st floor, no A/CbrPARKING: Driveway (5 vehicles)brbr-- THE LOCATION --brbrFISHING: Sadawga Lake (5 miles), Lake Whitingham(8 miles), Harriman Reservoir (8 miles)brOUTDOOR REC: Deerfield Valley Sportsmen’s Club (3 miles), Molly State Park (5 miles), Hogback Mountain Conservation Area (6 miles), Hogback Mountain (7 miles), Harriman Reservoir (8 miles), Haystack Mountain (10 miles), Mount Snow Grand Resort (14 miles), Natural Bridge State Park (27 miles)brAREA HIGHLIGHTS: Wilmington Village Historic District (4 miles), Honora Winery & Vineyard (4 miles), Hermitage Club (9 miles), Creamery Covered Bridge (20 miles), Retreat Tower (21 miles), Bridge of Flowers (22 miles), MASS MoCA (28 miles)brAIRPORT: Albany International Airport (64 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 smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID will be required upon check-in to ensure the guest on the reservation meets the 25-year-old age requirementbr- NOTE: There is no swimming in the pondbr- NOTE: Check-in and check-out times are flexible upon request (reach out to the homeowner for more information)br- NOTE: The firewood in the mudroom is for the indoor fireplace only. Guests are responsible for bringing firewood to use outsidebr- NOTE: This property requires stairs to accessbr- NOTE: The property does not offer A/C

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Sleeps

$521

/ Nightly

Private Vacation Home

GAMERS HAVEN, River Wine Inn!

Whitingham, Vermont, United States

Experience endless enjoyment in this charming 4-bedroom converted winery, where every room promises relaxation and excitement. Nestled amidst serene surroundings, you'll discover hiking trails right in the backyard, a picturesque pond inhabited by a beaver, a gazebo and a flowing river with a quaint wooden bridge leading to an expansive parking lot accommodating up to 10 cars. brbrIndoors, an inviting barn houses a plethora of entertainment options including half-court indoor basketball, Ping-Pong, 2 arcade games, corn hole, digital piano, darts, over 20 board games, shuffleboard, foosball table, mini golf, poker table, pool table & more. The outdoor hot tub on the back deck offers stunning views, complemented by a spacious field perfect for disc golf and outdoor picnics near the fire pit or at the nearby picnic tables. brbrConveniently located within walking distance, you'll find a bakery, country store, and a full restaurant and bar, ensuring you have everything you need without having to drive. Just a short 20-minute drive to Mount Snowe and 20 minutes to Berkshire East Mountain, adventure awaits. There is skiing, alpine slides, fly-fishing, white-water rafting, sip lines, mountain biking, hiking, tubing and more.brbrStay connected with Wi-Fi throughout the property, supplemented by free town Wi-Fi near the roadway. For those needing to work remotely, two dedicated spaces with cozy desks are available. Additionally, two separate living rooms and refrigerators on opposite sides of the home enhance convenience and comfort. brEnjoy the luxury of organic soaps, shampoos, and conditioner, along with fresh towels provided for each stay. Each bedroom features a soothing sound machine and a cozy sitting area, offering a perfect retreat for personal relaxation.brbrGather around the expansive dining table that seats 10, ideal for creating cherished memories over meals. Throughout the property, endless picturesque spots beckon for exploration and photo opportunities.brbrFor entertainment, sync your music through the Sonos app and enjoy it throughout the house, or connect to the massive speaker in the barn while engaging in indoor basketball. For a truly immersive experience, venture down to the river and unwind in the hammock nestled under the bridge.brbrThe owners thought of every possible need in the kitchen including individual charcuterie boards for each guest along with a Wok, air fryer, taco holders, spices, luxury teas, extra coffee pot along with a Keurig pot, Ninja blender, Crockpot, fondue kit and desert displays. Enjoy a complimentary bottle of wine and snacks upon arrival and a free drink(s) coupon to the local bar within walking distance.

4

Bed

3

Bath

12

Sleeps

$658

/ Nightly

Chalet

Chalet- Stream, A/C, Hot Tub, min to Lake and Ski

Whitingham, Vermont, United States

Family Friendly Chalet perfect for all season's . Minutes from Beautiful Wards beach at Lake Whitingham and 15 minutes from Mt Snow and the Hermitage mountain Skiing. 5 minutes from quintessential Vermont town of WilmingtonbrSummer:brWalk to the amazing non developed lake. you can Kayak, boat, fish. Stream runs along the property. Pond in the rear of the property.brWinter: brSnowmobile & snowshoe right outside the door. 15 Minutes from MT Snow and the Hermitage clubbrFall: brFoliage, Hiking, Breweriesbrbr6 Bedroom/2 Bath sleeps up to 18 guests. brGround level- bedroom#2,3,4br1st level- bedroom#1br2nd Level- bedroom#5,6brNew Hot Tub right outside the Master bedroom in the ground levelbrbr* - Primary renter must be 30 and overbrbr*- Pets will be considered( Type, size, etc) for a fee of $75/ up to 3 night stay. $150 for anything over 4 nights. Please inquire about your pet before booking.)brbr*- Once Booking is confirmed a rental agreement will be required to be signed with a photo idbrbr*- A preauthorization charge of $500 will be placed on your CC in leu of a refundable security deposit just prior to checkout. This charge will be released no later than 5 days from your departure.brbrThis property has additional guest fee beyond 12 guest. The additional pricing will show in your booking amount but does not show correctly on the VRBO platform. VRBO is working to resolve this issue.br* - Primary renter must be 30 and overbrbr*- Pets will be considered (Type, size, etc) for a fee of $100 per pet / up to 3 night stay. $175 for anything over 4 nights. Please inquire about your pet before booking.)brbr*- Once Booking is confirmed a rental agreement will be required to be signed with a photo id

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$287

/ Nightly

Private Vacation Home

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Whitingham, Vermont, United States

Bring the whole family (or two) to this historic 1865 home with lots of room for fun. This 5 bedroom antique New England home is situated between Lake Whitingham and Lake Sadawga. 11 minutes from Wilmington , 25 minutes from Mt Snow or Berkshire East. You can boat, ski, fish, swim or hike. It's the perfect house for families to vacation with a game room on the third floor including ping pong and fuse ball. brbrThe house sleeps 10 comfortably with a pull out couch in the downstairs living room for up to 12. The kitchen has all amenities (coffee maker, slow cooker, blender, etc), a live edge wood countertop, washer and dryer. It looks out over the living room so no one has to be left out while they cook. That open space leads into a dining room overlooking the yard where you can watch the local wildlife and listen to the brook flow by. A separate space on the first floor is a media room so you can enjoy a movie or a game. A half bath rounds off the first floor. The second floor has 5 bedrooms and 2 bathrooms including two showers and a soaker tub. The third floor is entirely a game room with ping pong, fuse ball, basketball and more. The backyard has a dining area, backyard games and a firepit. The brook runs at the back of the property and you can dip your toes on those hot days. There is plenty of space for a family or two to enjoy a wonderful time in the Green Mountains skiing, hiking, swimming, exploring one of the many shires or attending one of the many local festivals year round. brbrThings to do: brMt. Snow (skiing) : 25 minutesbrBerkshire East (skiing, biking, white water rafting): 25 minutesbrProspect Mtn (skiing) 20 MinbrLake Whitingham (boating, fishing, swimming): 1 minute drive, 5 minutes walkbrLake Sadawga (ice fishing, fishing and swimming): 1 minutes drive, 5 minutes walkbrWilmington Center (shopping, summer flea marker): 11 minutesbrJacksonville (live music): 5 minutesbrNorth Adams (Mass MOCA): 30 minutesbrPine Hill Orchard (apple Picking): 20 minutesbrHiking: Everywhere... Our driveway is monitored by camera to ensure arrival and departure but has no audio.

Bed

Bath

Sleeps

$653

/ Nightly

Private Vacation Home

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham, Vermont, United States

Welcome to Pi π aka Lakefront Loft. A one of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. brOur spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Bedroom 1 we've nicknamed the glass bedroom with three sides floor to ceiling total glass windows. Bedroom 2 has two large floor to ceiling windows and a 55 inch tv. Bedroom 3 is accessed by the custom made cherry wood spiral staircase. This bedroom has led multi-color changing lights in the ceiling and a sliding glass door to your own private balcony. brOur kitchen is fully equipped with western sunset views. This full kitchen with an 18 foot counter has state of the art appliances, a direct inline Keurig coffee maker (never have to fill the water again!) All utensils including pots, pans, etc., for those big family dinners or late morning breakfasts. Have your meals together on our very cool dining room table made from a shipping container door! Don’t want to eat in the kitchen Well there are three deck levels allowing for all kinds of dining experiences including a rooftop deck with propane firepit. brThe Living Room is a perfect space with a 65 inch FRAME TV and 54 inch built in driftwood log gas fireplace operated by remote control. This perfect space can double by opening the huge accordion style glass doors to your enormous deck space with its own propane firepit. Perfect for drinks, games, and conversation. The house is well stocked with bedding, linens, and includes a washer and dryer. Your comfort is of utmost importance. There is radiant heated flooring as well as mini split units providing AC in every living space.brbrThere are extensive grounds outside the house that include three deck levels ( each with direct piped in propane 40 inch lava rock firepits, hot tub (with heated deck mats in the winter), custom-built sauna and more. Just steps away is Sadawga Lake, where you can fish, kayak, hike, ice skate, or sit near the waterfall and enjoy the sun. Less than a mile away is the Harriman Reservoir southern boat launch. There are so many nearby attractions, including skiing, snowboarding, snowmobiling (VAST trail down the street), hiking - not to mention numerous shops, restaurants, and breweries. We own the local general store and Taproom (bar/restaurant) with live music every weekend, pool table, skeeball and shuffleboard with a cool automotive theme throughout. Just 4 miles down the street. AND we deliver groceries, prepared meals and our famous 20 inch New Haven style pizza. We are told we have the best gluten-free pizza.

Bed

Bath

Sleeps

$417

/ Nightly

Private Vacation Home

Beaver's Bend Lakefront Retreat ~16 mi to Slopes & Pet Friendly!

Whitingham, Vermont, United States

Tucked away in the bends of Whitingham, you’ll find our family’s home - 2nd Fiddle, where our Irish touch is sure to make you feel at home & our NYC energy will keep you entertained. Our home is stocked with paddle boards, canoes, blow up rafts, games, Smart TV's, grill & more. To enjoy all Vermont has to offer, we are across the road from Harriman Lake & only 30 minutes from Mt Snow, with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!brbrWe have a s spacious patio/porch with plenty of outdoor furniture with a grill and 2 dining tables overlooking our beaver pond and Lake Harriman. Enjoy our basement with L shaped couch, large TV, pool table, ping pong, and board games. We have a kitchen stocked with spices, tools, and pots & pans galore.

3

Bed

4

Bath

10

Sleeps

$208

/ Nightly

Private Vacation Home

The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome

Whitingham, vt, United States

Nestled on a dead-end road on ten private acres, the home has two upstairs bedrooms, each with queen-sized beds, and an additional full-size bed in the living room. There is one full bathroom with a tub and shower, washing machine, and dryer. The kitchen is a fully equipped open layout with a NEW GE electric stove and oven, refrigerator (18 cubic feet), microwave, coffeemakers (Keurig and brew), toaster oven, and dishwasher. The backyard has a campfire area and a fire pit.brYear-Round Activities, restaurants, and shopping available in ...brNorth Adams & Adams, MA (35 minutes)brWilmington, VT (15 minutes) brJacksonville, VT (8 minutes)brBrattleboro, VT (40 minutes)brMt. Snow, VT (30 minutes)brGreenfield and Northampton, MA (40 minutes)brBennington, VT (45 minutes) brbrAsk us about our favorites!brbrVTEL High Speed 4G LTE Wireless Internet brCellphone accessbrVonage landline telephonebrDISH HD/SIRIUS XM, 42' HDbrNEW Rinnai ON DEMAND water heater and propane heaterbrQUADRA-FIRE 4300 wood-burning stove with glass door (firewood included) Furnished deck with BBQbrSorry, No Smoking! brParking Included on Premises (please note that we recommend 4WD in the winter as we cannot guarantee the availability of plowers for a private road)

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Bath

Sleeps

$253

/ Nightly

Agritourism

Ski Season! Play Area, Crib, 11 Acre Farmhouse

Whitingham, Vermont, United States

Unwind with your loved ones at this cozy historic farmhouse on 11 acres of Vermont forest. Carley Farmhouse is a retreat for families with young children, pets, and anyone who needs a Vermont escape. Built nearly two hundred years ago, the home is nestled on a quiet country road above Lake Sadawga.brbr* Art & activity area for children ages 1-8br* 2 fireplaces and 1 wood pellet stovebr* Stunning meadow view, fireflies in summer, birdsong morning and eveningbr* Outdoor fire pit, front porch sitting area, 3-season sunroombr* High-end wood crib, baby blankets, baby changing pad, baby gatebr* Pet friendly, pet food and water bowls, pet towelsbr* 300 Mbps upload-download high-speed fiber optic WiFi, remote worker friendly, LG 31.5-inch 1920 x 1080 monitor, HDMI cable, Herman Miller Aeron chairbr* Spa quality linens and toiletriesbr* Clawfoot tub with oil-rubbed bronze fixturesbr* Fully-equipped kitchen, Le Creuset dutch ovenbr* Complimentary local maple syrupbr* 2 Kings, 1 Queen, 1 fold-out Queen sofa, 2 Twin cotsbr* LG OLED C3 Smart TV with complimentary Netflix, HBO Max, Disney+, Hulu, ESPNbr* Puzzles, board games, grown-up art suppliesbr* Brand-new Miele washer & dryerbr* 4-minute drive from the Harriman Reservoir South End Boat Rampbr* 20-minute drive from Marlboro Music Festivalbr* Great discount for 7+ day stays!brbr---brbrA walkthrough of the home:brbrEnter off the charming wood front porch into the foyer. Be greeted by warm wide-plank pine floors and original rough-hewn exposed beams. Warm up at the gorgeous fireplace with hand-carved mantel in the first floor living room, or at the pellet stove. We supply pellets.brbrCook your grandmother's recipes in the fully-equipped kitchen. Pass the day in the dining room with its copper-roofed south-facing bay window. Sit around around the hardwood dining table, and watch the birds flit around the quince bushes.brbrLet your kids' creativity fly in the art and activity area for young children ages 1 to 8, designed by an early childhood educator! Create art with easel, watercolors, tempera paints, chunky brushes for small hands, pastels, markers, and colored pencils. Build with hand-made solid maple blocks. Enjoy sensory enrichment with playdough, coloring books, stuffies, and Magna-Tiles.brbrEnjoy the best sleep of your life in stunningly comfortable beds with spa-grade toiletries and linens, and real duck down duvets in the winter. Each bedroom has a picture-perfect forest view. Wake up to birdsong and frogs calls from the pond.brbrThe second floor opens into a bonus living room arranged around a 55 LG OLED C3 Smart TV and Sonos Arc sound bar, balanced by a red-enameled cast iron stove. The TV comes with complimentary streaming subscriptions, so you can pick up with any and all the shows you're watching!brbrOpen spring through fall, the peaceful three-season sunroom looks north into pristine forest. It's our favorite place to have coffee. Throughout summer, watch thousands of fireflies dance across the meadow.brbrThe downstairs bathroom has a simple stall shower. The upstairs has a clawfoot tub with oil-rubbed bronze gooseneck shower. Laundry No problem. Enjoy the brand-new Miele washer and dryer in the first floor bathroom.brbrThe acreage spans 11 acres with fields, forest, a small pond, and babbling streams.brbr---brbrThe whole house and 11 acre grounds are for you to enjoy!brbrPlease do not enter the basement. Please don't swim in the retaining pond in the back yard.brbrRural Whitingham has limited cell service. We recommend to download offline maps before venturing out! Wilmington, a 13-minute drive north, has cell reception.brbrIf you are planning to build a fire, we recommend to pick up kindling at a hardware or general store.brbrIn the rainy seasons, the lawn gets soggy. Bring waterproof boots if you'd like to walk the acreage! When coming in the winter or rainy seasons, please take care not to slip on the steps onto the front porch or into the sunroom in the back.brbrIn the warm season, our landscaper may occasionally come to the property to mow grass and water trees.brbrWe can host up to 8 people, but we find 4-5 adults is the sweet spot. Our pricing incorporates a small extra guest fee, per person per night, for the 6th and above guest. The upstairs living room has a cozy loveseat that can sleep a toddler, and a 3-seat couch that can sleep an adult. The downstairs living room has a sleeper sofa with queen mattress. Two additional twin mattresses and folding bedframes are available to guests self-serve in our storage room.brbrSemi-seasoned cord wood is available on the property for a nominal fee.brbrPlease use caution if entering the garage. Landscaping tools and materials are stored there. The garage is not suitable for children and pets.brbrOur home welcomes cats and dogs. Though we clean exactingly between each reservation, we recommend to bring allergy medications if someone in your party has pet allergies.brbrWe have two security cameras on the property. One faces outward over the front porch, and one faces outward from the garage.

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Bath

Sleeps

$392

/ Nightly

Private Vacation Home

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham, Vermont, United States

The 3000 sq ft house is located on 13.5 acres. The yard & house faces south, so warm & sunny. Mount snow ski area is 20 miles away, the town of Wilmington is 12 miles away and the town of Readsboro is 2 miles away. Readsboro has nice general store with mainly food & beverage as well as gasoline. The Readsboro Inn is a full restaurant and bar as well there is a nice breakfast eatery down the street. There is quick access to the VAST snowmobile trail through the back yard. Atherton meadows state wildlife management area is a short hike away up through the backyard. Thunder Mountain Bike Park is another fun activity only 14 miles away down into MA.br The house was built in the late 70's. The furnace is an oil burner - forced air system, as well as a large wood burning stove. There is a full concrete basement. The cooking stove is propane as well as the tank less hot water heater. brThere are 2 bedrooms down stairs, the larger bedroom has a full & a twin bed, the other has 2 single beds. There is a full bath downstairs with a shower and tub. Upstairs the is a full bath with a large shower. There are 2 large bedrooms upstairs, one of the rooms has 4 twin beds & a king, the other has 2 twins & a king . There is plenty of room for air mattresses and foam for kids to sleep on.brThe house is very spacious and functional for big groups. br You enter through a slider on the right side of the house next to the drive way into the wood burning stove room / TV room. Which has couches for 8 to 10 to sit. There is a big coat / boot room to the right and the laundry room is next on the right.brThen straight ahead into the kitchen. There is a bar with stools that is open into a large room on the left that has couches and a bumper pool table. The kitchen has two large tables for eating and endless chairs. There is a door in the middle of the kitchen into the backyard.brAt the far end of the kitchen is a hallway that leads to two bedrooms, bathroom and the up stairs. This is a country home geared toward large families with kids and pets. The house is clean with very little clutter and things for kids to break. Few things are brand new but nothing is trashed or ripped up. There is rail around the wood burning stove to keep kids away and for drying clothes. The kitchen is loaded with pots, pans, plates, silverware, cups, glasses and everything a kitchen could need. Big gas stove, oven, dishwasher, microwave, toaster, coffee maker & keurig etc..br The yard and surrounding woods are perfect for year round outdoor fun. The only neighbor is in deep in the woods across the street. The property is surrounded by state forest perfect for hiking, snowshoeing, cross country skiing, mountain biking and snowmobiling. The yard is a huge 13 1/2 acre rolling hill that faces south getting plenty of sun. Roughly 1/2 of the property is mowed grass with level areas behind the house and up the yard for outdoor functions, picnics and games. There is a nice level area to set up a badminton or volley ball net. The yard winds up the hill to offer beautiful mountain views of sunrise and sunset. Winter time sledding is endless. The driveway goes straight up the hill with ample parking down by the road and up into the yard. There is a beautiful flowing creek the winds down the right side of the yard. In the spring and summer the yard is fill with flowers, 5 different types of apple trees, a pear tree, 2 blue berry bushes and endless red and black raspberries. Lake Whitingham has a public boat launch a couple miles down the street for all types of boating and fishing. The other direction up the street near Readsboro is the Sherman reservoir which is part of the Deerfield River, great for fishing and kayaking. Both lakes are also great for swimming and just floating on a tube on a hot summer day.br br

4

Bed

2

Bath

15

Sleeps

Vacation Rentals By Owner In Whitingham, VT

$175

$302

$206

$447

$881

$328

$488

$748

$814

$463

$521

$658

$287

$653

$417

$208

$253

$392

Most popular vacation rentals in Whitingham

$652.96

$253.14

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$520.78

$643.11

$205.60

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$175.47

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