Holiday rentals 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, 174 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
4.99 out of 5 average rating, 164 reviews

Trailside Stays - Tiny House in the Woods-Blue Jay

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
Two red Adirondack chairs are positioned around a circular fire pit in an open grassy area. A backdrop of lush green trees and distant mountains is visible under a partly cloudy sky.
Cottage in Wentworth
4.88 out of 5 average rating, 138 reviews

Fun Get-away with Grand Views in White Mtns, NH

A perfect place for a mountain get-away where you can unplug, relax and enjoy the fabulous mountain view and wildlife. Cottage has all you need for a comfortable stay....grill, queen size bed, wifi, A/C, fully equipped kitchen, fluffy towels, fire ring and it is located in the heart of the White Mountains, close to all outdoor activities, just minutes away from Rumney Rock. Stay here for your entire stay or return after visiting this great area. Just 20 minutes from restaurants and interstate.

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.
Flat in Wilmot
4.96 out of 5 average rating, 107 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
Cabin in Alexandria
4.97 out of 5 average rating, 156 reviews

Handcrafted A-Frame near Newfound Lake & Hiking

Unplug at Millmoon A-Frame Cabin just 2 hours from Boston - Recharge under the stars by the fire pit - Relax or 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 Need more space? Visit Darkfrost Lodge + sauna airbnb.com/h/darkfrostlodge Stay at NEW Black Dog Cabin + sauna airbnb.com/h/blackdognh

Top guest favourite
A charming wooden cabin is surrounded by lush greenery, with a sloped roof covered in red metal. Large windows provide ample natural light, while a gravel path leads to the entrance, inviting guests to explore the serene rural setting.
Tiny home in West Fairlee
4.96 out of 5 average rating, 188 reviews

Off Grid Tiny House

This sweet little house is great for those who want to get away from it all. It's like camping but with many more creature comforts. The house has hot and cold water in the summer but is off for the season now, end of October. The house does not come with sheets and towels but if you need that, please let me know and I’ll make that happen for a small fee ($15)! Great for kids! Mountain biking and hiking locally and right out your door. 10% veteran discount. Spectacular and cozy in the winter.

Superhost
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, 168 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, 105 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
The exterior view showcases a multi-level log home with a wooden deck and elegant round window. Outdoor seating is provided on the patio, surrounded by lush greenery and decorative plants, creating a serene entryway to the private apartment below.
Flat in Wentworth
4.94 out of 5 average rating, 282 reviews

White Mountain Log Home Retreat

Lovely, private apartment in log home on 42 acres. Open concept, queen bed, leather sectional couch, eat in kitchenette (micro, electric frypan, two burners, good size fridge),full bath. Close to White Mountain National Forest trails and 8 miles from AT (Appalachian Trail), minutes from Rumney Rocks (world class climbing), on snowmobiling trails,canoeing/kayaking, skiing, and swimming. 8 miles from Green Woodlands with outstanding groomed cross country skiing and mountain bike trails.

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, 240 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.

Top guest favourite
A spacious apartment is reflected in the calm water of a pond, surrounded by lush greenery. The building's exterior features large windows and a welcoming design, while the natural landscape adds to the serene setting.
Flat in Thetford
4.99 out of 5 average rating, 142 reviews

Charming & Peaceful Upper Valley 1BR Retreat

A beautiful one-bedroom apartment in the heart of the Upper Valley. Walkout basement apartment with private entrance and lots of natural light. Full kitchen stocked with all the equipment you need to cook your meals. Sleep comfortably on the queen-sized bed. High-speed internet (100Mbps), Smart TV. Patio with seating area overlooking our pond. Perfect for couples or solo adventurers. Easy driving distance to Hanover, Norwich, Lebanon, Lake Fairlee, Lyme. 1.5 miles to highway 91.

Top guest favourite
A charming cottage is set among lush greenery, featuring a dark wooden exterior. A spacious deck with seating options invites outdoor relaxation, while large windows provide natural light. A small pathway leads to the entrance, enhancing accessibility to the tranquil surroundings.
Cottage in Piermont
4.98 out of 5 average rating, 147 reviews

Fully Updated, Quiet & Cozy 1-Bedroom Cabin

Escape To Tuckaway Cottage - This perfect-for-two entire cottage is freshly remodeled, clean, comfortable and centrally located for your New Hampshire and Vermont adventures! All new furnishings and fixtures, a fabulous outdoor fire pit, and a wonderful enclosed porch with patio are just a few highlights. A short drive in any direction offers 4-season outdoor recreation with nearby mountains, lakes and rivers, plus dining, culture, and entertainment options abound.

Popular amenities for Dorchester holiday rentals