House vacation rentals in Whitingham

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Top-rated house rentals in Whitingham

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Top guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.95 out of 5 average rating, 156 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Superhost
A Victorian mansion is set amidst a spacious lawn bordered by natural stone walls. The exterior showcases multiple gables, a large front porch with rocking chairs, and numerous windows. Leafless trees frame the property, hinting at the changing seasons.
Home in Whitingham
4.94 out of 5 average rating, 103 reviews

Lakeside Victorian Mansion w/Hot Tub Near Skiing

WE now pay the 15.5% Guest Service Fee!!! An experience like no other... 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. WEDDINGS!!!Our house is close to boating, fishing, skiing, snowboarding, hiking, and all that VT has to offer.

Guest favorite
Home in Colrain
4.9 out of 5 average rating, 143 reviews

The 1770 House

Spring is the most dramatic time here. At the end of a dirt road with no cars or people you are one with nature. Ask to see if the pool and outdoor spa are open. In March and April our rates are discounted 20%. Enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views of Vermont. There are six bedrooms and three bathrooms.

Top guest favorite
A inviting outdoor space features two blue Adirondack chairs paired with a fire pit, where flames reflect off colored glass. A hot tub is visible nearby, surrounded by greenery, enhancing the tranquil ambiance of the area.
Home in Wilmington
4.96 out of 5 average rating, 143 reviews

Walk To Town, Hottub, Firepit, Games, Mt Snow

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

Guest favorite
A bathroom features natural wood paneling and a brick accent wall. A compact vanity with a sink is complemented by a mirror and overhead lighting. Shelves hold neatly folded towels, while a washer and dryer unit is integrated into the design, presenting a functional space.
Home in Wilmington
4.91 out of 5 average rating, 260 reviews

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

Top guest favorite
A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.
Home in Whitingham
4.92 out of 5 average rating, 119 reviews

Vermont lake house near Mt. Snow-fab 360 views!

Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms, and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Top guest favorite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington
5.0 out of 5 average rating, 134 reviews

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Guest favorite
A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.
Home in Ashfield
4.97 out of 5 average rating, 106 reviews

An 18th century farmhouse

Built in 1785 this antique Cape was carefully restored to its original design about 20 years ago. The house is set on a quiet road in the middle of fields, woods, gardens, and hiking trails. it is secluded with easy access to the natural world. The rooms are book-lined and filled with family objects. It is close to Berkshire East for skiing and snowboarding in the winter and whitewater rafting and swimming in the summer. Mass MoCA and the Clark Museum are within an easy drive.

Guest favorite
A well-maintained home features a spacious porch with green chairs and is surrounded by a lush lawn and trees. The gravel driveway offers ample parking space, while the bright blue sky enhances the serene outdoor setting.
Home in Wilmington
4.94 out of 5 average rating, 319 reviews

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

Guest favorite
A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.
Home in Wilmington
4.89 out of 5 average rating, 180 reviews

Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow

Escape to the mountains in this cozy 4BR, 2BA Chimney Hill cabin, just 15 minutes from Mt. Snow and minutes from downtown Wilmington. Gather around the outdoor fire pit, cozy up by 2 fireplaces, or enjoy access to the nearby community clubhouse with indoor & outdoor pools, hot tub, fitness room, and more. Sleeping up to 8, the home is perfect for families and groups looking for skiing, hiking, lake days, foliage, or a relaxing Vermont getaway year-round.

Top guest favorite
Home in North Adams
4.98 out of 5 average rating, 555 reviews

Steps to MoCA private house + SAUNA!

Welcome to the Gardener’s Cottage at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just houses, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Top guest favorite
The lakefront home features a rustic wooden exterior with multiple balconies overlooking the water. Surrounded by lush greenery, the property includes a sprawling lawn and vibrant shrubs, while the serene lake and gentle hills can be seen in the background.
Home in Whitingham
4.99 out of 5 average rating, 102 reviews

Gorgeous Vermont Lakefront with epic sunsets!

Lakefront home with breathtaking 180 degree views of Sadawga Lake and the Green Mountains. The house is on 3.5 acres of land with 600 feet of lake frontage which includes a private dock. If you are looking for an exceptionally peaceful and relaxing lakeside get away or an action packed weekend in the outdoors this house will meet all your needs. Skiing, hiking, biking, boating, paddling and swimming are all right here!

Popular amenities for Whitingham house rentals