
Holiday rentals in Surry
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Top-rated holiday rentals in Surry
Guests agree: these stays are highly rated for location, cleanliness and more.

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.
ValueLocationBack garden
4.99 out of 5 average rating, 179 reviews
Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)
LocationValueTV
4.88 out of 5 average rating, 291 reviews
Cozy and Romantic Granite Lake Cottage Getaway
Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.
LocationFamilyCleanliness
4.99 out of 5 average rating, 147 reviews
Village Flat with Antique Billiards
Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.
FamilyValueHiking
4.94 out of 5 average rating, 283 reviews
Cozy Downtown Getaway!
Welcome to our charming Airbnb nestled near downtown Keene, New Hampshire! Our property offers a cozy and welcoming retreat for guests looking to experience the vibrant culture of this historic city. With its convenient location, you'll find yourself just a short stroll away from the bustling shops, eateries, and attractions that downtown Keene has to offer. The spacious Airbnb boasts 3 bedrooms, 2 bathrooms and ample living spaces making it ideal for families or groups of friends traveling.
FamilyLocationPets
4.87 out of 5 average rating, 83 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.
FamilyLocationCheckout
5.0 out of 5 average rating, 124 reviews
Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.
ValueLocationComfort
4.97 out of 5 average rating, 202 reviews
Owls Nest Treehouse
Tiny cabin Treehouse retreat with a small farm store with Local Goods on site. Located 30 minutes from Keene and 20 minutes from Bellows Falls, VT, this Owl's Nest is tucked away in a privately owned forest, surrounded by nature on a small homestead. Kitchenette, rainfall shower, full Wi-Fi, TV and Private Hot Tub. Be sure to check out the Guidebook for Local Recommendations. Activities & Eateries of all kind just a short drive away.. Only sleeps 2, no pets, not handicap accessible
LocationComfortLayout
4.99 out of 5 average rating, 103 reviews
The Brick House on Washington Street
Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.
ValueLocationWalkability
4.93 out of 5 average rating, 251 reviews
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Discover the ultimate outdoor experience in Southern NH! Enjoy a year-round private hot tub in a covered gazebo, fire pit, hammock, life-size games, and swing set. Located in one of Keene’s safest, quietest neighborhoods, walking distance to downtown and across from Keene Ice Rink. Close to beaches, hiking, and ski resorts. Features a fully stocked chef’s kitchen, wine cooler, and luxury Purple mattresses with individual mini-splits in each bedroom for optimal comfort.
LocationValueCondition
4.98 out of 5 average rating, 215 reviews
Modern 6BR Home for Large Groups & Families
Welcome to your expansive New Hampshire getaway—a beautifully designed, modern home with over 4,000 sq. ft. of living space, three full levels, and room for up to 12 guests to relax, recharge, and enjoy time together. Perfect for multiple families, group trips, UNH/Keene State visits, and extended stays, this home offers every comfort imaginable plus thoughtful touches to keep large groups connected without ever feeling crowded.
FamilyLocationBathroom
4.73 out of 5 average rating, 22 reviews
Charming Country Home
Charming one level ranch style home. Quiet country neighborhood 5 miles from Keene, NH, 10 miles from Brattleboro, VT. The home has a fully equipped kitchen, smart TVs, spacious rooms, two bedrooms, two full baths, laundry in basement, couple of steps to master bedroom. Great backyard. Spacious driveway with motion lights.
FamilyValueWalkability
4.98 out of 5 average rating, 318 reviewsPopular amenities for Surry holiday rentals
Other great holiday rentals in Surry

Walpole NH Peaceful Farmhouse Getaway-VT/NH Border
LocationFamilyBreakfast
5.0 out of 5 average rating, 92 reviews
Sunnyside Farmhouse with lots of outdoor spaces
ValueFamilyGrill
4.98 out of 5 average rating, 60 reviews
Country Cottage
FamilyLocationCleanliness
4.94 out of 5 average rating, 49 reviews
Charming, Large House in Walpole NH /VT. Border
FamilyLocationAmenities
4.98 out of 5 average rating, 92 reviews
Family-Friendly 3BR Historic Home – Walk to Keene
FamilyLocationAccuracy
5.0 out of 5 average rating, 20 reviews
Cozy Cottage Loft and Retreat
LocationWalkabilityQuiet
4.98 out of 5 average rating, 61 reviews
The Boat House on Granite Lake
ValueFamilyKitchen
5.0 out of 5 average rating, 31 reviews
The Murdock Suite @ The Large House
ValueLocationIndoor spaces
4.95 out of 5 average rating, 82 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Pats Peak Ski Area
- Berkshire East Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Snhu Arena
- Dartmouth College
- Ragged Mountain Resort
- Bear Brook State Park
- Hildene, The Lincoln Family Home
- Killington Resort
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Montshire Museum of Science
- Camp Plymouth State Park
- Quechee Gorge
- The Montague Bookmill
- New Hampshire Motor Speedway





