Holiday houses in Dorchester

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Top-rated holiday rentals in Dorchester

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

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Top Guest favourite
Tiny home in Wentworth
4.99 out of 5 average rating, 194 reviews

Tiny Riverfront A-Frame w/ Mountain Views, Hot Tub

Welcome to 'The Alexander' @ Casa de Moraga! This tiny A-frame is nestled on the bank of Baker River w/ breathtaking views of the river & White Mountains. Full kitchen, bathroom w/ shower & living/dining area. Wake up in the loft bedroom & see the mountains & river from bed. Read on the couch & enjoy the gel fuel fireplace, take a swim or fish in the river - relax in your private hot tub on the deck overlooking the river! 10 min to Tenney MTN. 35 min to Ice Castles, Franconia, Loon & Waterville!

Top Guest favourite
Tiny home in Dorchester
4.97 out of 5 average rating, 206 reviews

Trailside Stays - Tiny House in the Woods-Escape to Nature. Snow Owl

This charming and elegant little cabin will transport you into nature. The feeling of camping outdoors with indoor amenities. Part of the brand-new campsite, Trailside Stays that is conveniently located alongside the ski and mountain bike trails at Green Woodlands. This tiny house features 1 high quality queen-size bed, linens, kitchenette, large picture windows, bathroom with shower, heating and A/C, outdoor seating and grill top fire pit. Don't see your dates available? Check the other cabins!

Top Guest favourite
A cozy living area showcases a comfortable sofa adorned with patterned cushions and a soft throw. A rustic coffee table sits in front, complemented by stylish armchairs. Natural light filters through large windows, illuminating the modern kitchen with dark cabinetry in the background.
Tiny home in Fairlee
5 out of 5 average rating, 173 reviews

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Guest favourite
The serene riverbank features smooth rock formations and lush greenery, with the gentle flow of water reflecting the surrounding trees and hills. The landscape captures a sense of tranquility, highlighted by natural elements gradually merging with the water's edge.
Guest suite in Ryegate
4.92 out of 5 average rating, 240 reviews

Secluded Paradise on the Connecticut River, VT

Close to heaven for artists and nature lovers. Guest space is the entire first floor of 47' round house with six foot picture windows which allow a 180 degree views on a private half mile on the Connecticut River. Extensive gardens, 30' private guest porch overlooking sandy beach and natural swimming vortex. 4 kayaks, firepit on river's edge, rope hammocks on riverbank. Northlight studio, queen bed ,and foldout couch,divided from bedroom by curtains. Small kitchenette and dining room area.

Top Guest favourite
The cabin features a gabled roof and large front windows, allowing natural light to fill the space. Surrounded by tall trees, the tranquil approach showcases a well-maintained pathway leading to the entrance, with soft sunlight filtering through the foliage.
Cabin in Grafton
4.98 out of 5 average rating, 220 reviews

Nature cabin | fire pit, fireplace, yard + privacy

The WildeWoods Cabin is a sunny open-concept cabin with cathedral knotty pine ceilings & exposed beams; renovated with comfortable furnishings, modern amenities, vintage décor & a gas fireplace (on/off switch!). Enjoy peace & privacy on 1+ acres; the cabin is set back from the road and surrounded by yard, gardens, & tall trees. Nestled in the foothills of Cardigan & Ragged Mountains; there are endless outdoor activities nearby. Up to 2 dogs are welcome with pet fee. IG: @thewildewoodscabin

Top Guest favourite
A window frames a serene external view, showcasing bare trees and a distant hillside. Soft light filters through, subtly illuminating the indoor space. A glimpse of a shed is visible among the foliage, highlighting the rustic charm of the surrounding landscape.
Apartment in Wilmot
4.97 out of 5 average rating, 127 reviews

Bog Mt Retreat Downstairs Suite

Welcome to your perfect first floor retreat. Woodland trails on the property, local hikes like BOG MT, a beautiful waterfall and so many more. Bring your kayaks and paddle Grafton Pond or Pleasant Lake and jump off the rock at Blueberry Island. Only 30 minutes from Sunapee Mountain Ski Area & 21 minutes from Ragged MT Ski Resort. Whether you're seeking the thrill of the slopes, the tranquility of nature, or a bit of both, our Airbnb is the gateway to an unforgettable New Hampshire experiences.

Top Guest favourite
A spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.
Home in Orford
4.98 out of 5 average rating, 153 reviews

Romantic Mountain Getaway

Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

Top Guest favourite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 570 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Guest favourite
A spacious porch is featured, with a light blue flooring and framed by wooden walls. Various seating options, including rocking chairs and a wicker chair, are positioned along the sides. Flower pots add vibrant color, while the surrounding greenery enhances the tranquil outdoor setting.
Cabin in Dorchester
4.88 out of 5 average rating, 177 reviews

Charming 2 bedroom cabin with amazing views!

Unwind and breathe the fresh mountain air. Sit at the kitchen table, sip your morning cup of coffee, and watch the fog clear to reveal breathtaking mountain views. During your stay, appreciate direct access to snowmobile and hiking trails as well as quiet country roads to bike ride. Nearby, enjoy the solitude of cross-country skiing on groomed trails. Challenge yourself rock climbing at Rumney Rocks or explore the Pemi River in kayaks and tubes. 20 mins. to specialty shops in Plymouth.

Top Guest favourite
The living area features a blend of warm wood paneling and natural light. A large sectional sofa is complemented by a comfortable armchair, with a coffee table positioned nearby. A desk is visible, offering a workspace, while a decorative rug adds texture to the floor.
Cabin in Dorchester
5 out of 5 average rating, 112 reviews

Stylish Cabin in Dorchester

Enjoy peace and quiet in the woods of Dorchester, at the foothills of the White Mountains! Elevated treehouse-style Cabin approximately 600 feet from the owner's main house. Tucked in the woods you will enjoy nature surrounded by moose, bear, deer, ermine, and more, while being only 15 minutes away from Plymouth. Close to Rumney Rocks climbing and countless hiking trails. Direct access to the amazing Green Woodlands for mountain biking in the summer and cross-country skiing in the winter.

Top Guest favourite
Cabin in Alexandria
4.98 out of 5 average rating, 195 reviews

Handcrafted A Frame near Newfound Lake and Hiking

Relax and recharge at Millmoon A-Frame Cabin just 2 hours from Boston - Exhale under the stars by the fire pit - Grill on the back deck w/ forest views - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Explore hiking, biking & snowshoeing nearby at Wellington and Cardigan Mountain State Parks & AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Guest favourite
The A-frame cabin is situated among tall trees, featuring a wooden exterior with multiple windows that allow for natural light. Illuminated from within, the front porch is adorned with potted flowers, creating a welcoming entrance against a moody sky.
Cabin in Rumney
4.94 out of 5 average rating, 256 reviews

Classic A-Frame with river, mountains, and hot tub

The “Baker Rocks” A-Frame is a new, well-appointed, and sits amidst a tranquil setting of river and mountain views. Nestled in New Hampshire’s Lakes and White Mountains Regions, the property is centrally located to dozens of attractions and activities. The house is fully equipped for a cozy weekend stay or a long retreat. The onsite amenities include direct river access, gym, small farm, playground, lounge area, and nearly 80 acres to explore. Firewood for sale on site for $5/bundle.

Popular amenities for Dorchester holiday rentals