Vacation rentals in Searsburg

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Top-rated vacation rentals in Searsburg

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Top guest favorite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford
4.94 out of 5 average rating, 132 reviews

Peaceful VT Chalet w/ Mountain View’s

Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Top guest favorite
Cabin in Wilmington
5.0 out of 5 average rating, 135 reviews

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Top guest favorite
Treehouse in Wilmington
5.0 out of 5 average rating, 114 reviews

Beautiful timber-frame treehouse

The timber frame treehouse is a perfect couples retreat. The home is custom built with hardwood maple trees cut down and milled right on the property. The deck has a barrel sauna, cold or hot cedar soaking tub, a propane fire pit, a wood burning chiminea fire pit, and a bar top for outdoor dinning. The inside has a stone fireplace, fully equipped kitchen, tile shower, projector with dvds, books, board games, chandelier, and dimmable lighting for any mood. This home is truly one of a kind.

Top guest favorite
A charming red cottage is framed by colorful autumn leaves, showcasing a sloped roof and multiple windows that allow natural light. A well-maintained lawn surrounds the building, with shrubbery adding to the inviting exterior. A grill is situated on the patio area to the left.
Guesthouse in Wilmington
4.99 out of 5 average rating, 69 reviews

Cozy, charming cottage 7 mins from Mt Snow & Lake

Take a deep breath & relax at this cozy, design-forward mountain cottage. Less than 10-minute drive from both Mt. Snow and two lakes, it's an idyllic getaway all year round. You'll stay in the guest cottage next to the main house. -Bunk bed handmade locally -Three outdoor fire pits -Nespresso w/ lots of coffee options -Aesop products -65in 4K TV w/ Sonos surround sound system -Fiber WiFi -Peloton -Weber grill with side burner -Sustainably sourced furniture -Local art & handmade goods

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 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.

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, 121 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 favorite
A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.
Apartment in Wilmington
4.98 out of 5 average rating, 540 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!

Top guest favorite
Chalet in Wilmington
5.0 out of 5 average rating, 131 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

Top guest favorite
A spacious living room features a large sectional sofa with decorative pillows, paired with a wooden coffee table. Natural light floods in through large windows, highlighting the hardwood floor. The adjoining dining area, visible in the background, includes a wooden table surrounded by several chairs.
Home in Wilmington
4.97 out of 5 average rating, 71 reviews

Vermont Village Retreat Near Mount Snow

Experience the charm of Wilmington Village in this sunny 3-bedroom home, just minutes from Mount Snow. Enjoy a spacious living area, a welcoming three-season sunroom, and a modern kitchen perfect for family meals. Step outside to explore local shops, dine at nearby restaurants, or embark on outdoor adventures year-round. A great family or friend getaway from the hustle and bustle!

Top guest favorite
A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.
Home in Bennington
4.99 out of 5 average rating, 353 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Popular amenities for Searsburg vacation rentals