Holiday houses in Whitingham

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Top-rated holiday rentals in Whitingham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious living area features modern seating arrangements with natural light streaming through large glass windows. A small table is set by the window, overlooking the garden. Polished wooden floors and decorative items add warmth to the inviting atmosphere.
Guesthouse in Marlboro Township
4.97 out of 5 average rating, 185 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

Guest favourite
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, 148 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!

Top Guest favourite
Home in Whitingham
5 out of 5 average rating, 18 reviews

Country home on 20 wooded acres with field views

Make memories at this unique house! Ideal for couples, families, biking/snowmobiling groups! The house is set on 20 wooded acres central to many summer and winter activities. Direct access off the property to the VAST trail system. Hiking, snowshoeing or snowmobiling, plenty of land for campers or tents, boat launch to Harriman reservoir just down the road, property hike to the largest glacial erratic in New England! 30 mins to Mt Snow, Berkshire East, Zoar, Thunder Mtn bike park, or MASS MoCA.

Top Guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 392 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Guest favourite
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
4.91 out of 5 average rating, 117 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.

Guest favourite
A living area is presented with warm red walls and wooden floors. A white couch, adorned with red pillows, invites relaxation. A small television is mounted on the wall. Natural light filters through windows, with a decorative lamp and potted plant adding character to the room.
Apartment in Whitingham
4.92 out of 5 average rating, 48 reviews

Vermont Lake Whitingham Mount Snow Area Apartment

Built in 1861 and located in the Lake Whitingham & Mount Snow area of Southern Vermont, walking distance to the village bakery, general store, and pub. The apartment opens to an edible garden housing chickens, ducks, and pollinators. Lake Whitingham is five miles North for swimming, hiking, cross country skiing, or kayaking. A little farther and you're in Wilmington's shops and restaurants. A 25 minute drive will put you at the foot of Mount Snow. This is a non-smoking property.

Top Guest favourite
A warm living area features high wooden ceilings and exposed beams. A cozy seating arrangement is set near a stone fireplace, adorned with holiday decorations. A television is mounted above the fireplace. Natural light filters through large windows, creating a welcoming atmosphere.
Cabin in Whitingham
4.98 out of 5 average rating, 131 reviews

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

Top Guest favourite
The cabin is situated among lush greenery, featuring a light green exterior that complements the natural surroundings. Large windows allow for ample light, while ferns frame the building at the front. The wooded area provides a sense of privacy and tranquility.
Cabin in Whitingham
4.96 out of 5 average rating, 127 reviews

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can Watch or stream favorite shows.

Top Guest favourite
Tiny home in Ludlow
4.96 out of 5 average rating, 105 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.88 out of 5 average rating, 113 reviews

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. 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 and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

Top Guest favourite
The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.
Cabin in Newfane
4.99 out of 5 average rating, 316 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Top Guest favourite
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, 101 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 holiday rentals