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Vacation rentals in Cheshire County

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Top-rated vacation rentals in Cheshire County

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

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Home in Putney

4.84 out of 5 average rating, 119 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)

Oct 30 – Nov 6

Apartment in Dublin

4.96 out of 5 average rating, 182 reviews

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

May 5 – 12

Cabin in Marlow

4.98 out of 5 average rating, 107 reviews

The Birches Cabin, at home in the woods!

The Birches is situated on 10 secluded acres, where guests will enjoy the privacy and scenery the cabin offers. Built in 2020 and designed to accommodate guests. During your stay take a walk on the property, read a book, enjoy a glass a wine, cook a fine meal, and stare at the stars. Centrally between Keene and the Sunapee region, guests have many options on how to enjoy their days such as Skiing, Hiking, Paddling, and Snow tubing. This is a vacation spot, that can be enjoyed all year.

Sep 6 – 13

Home in Putney

4.94 out of 5 average rating, 336 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Dec 5 – 12

Cabin in Stoddard

4.82 out of 5 average rating, 111 reviews

Cozy Cabin with Lake Access

Our cabin is situated in a private, peaceful setting surrounded by trees. Inside you will find a timeless lake house decor and everything you need for a relaxing vacation. A 1/4 mile walk or drive brings you to our private community lake access and boat ramp on beautiful Highland Lake. We offer use of our 3 kayaks (2 single/1 tandem) located next to the boat ramp. Nearby are great hiking trails and quaint villages. This is a wonderful place to unwind and have a truly fun & relaxing vacation!

Sep 16 – 23

Guesthouse in Fitzwilliam

4.86 out of 5 average rating, 331 reviews

Tranquil Guest House with Sauna & Hiking

Are you seeking to escape the city & take a break from hectic schedules & demands? We invite you to embrace life at a relaxed pace surrounded by nature, offering an opportunity to reset your life & cultivate space for stillness & healing. Enjoy the fire pit, walk the trails, forage for treasures & unwind in the wood fired sauna! We've created a place for you to unwind & restore your soul, & detox & recharge your body. For the full retreat ask about day pass to Covey House Healing Center.

Nov 26 – Dec 3

Apartment in Winchester

4.93 out of 5 average rating, 161 reviews

Downtown Loft above Winery and Distillery

Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door and a pint on us at Outlaw Brewing Company. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living/dining room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!

Nov 26 – Dec 3

Apartment in Keene

4.83 out of 5 average rating, 134 reviews

Lynda's Suite: Seasonal Stays

Welcome to The Phineas Handerson House, originally built in 1827 by the “the happiest man in town” Able Wilder. Modern eclectic one-bedroom apartment, just one block from Central Square in Downtown Keene. Featuring newly remodeled kitchen, fitted with electric range and microwave. Other tenants occupy part of the building, but guests have a private entrance and off-street parking behind the building. Comfortable for two guests but can sleep up to four. Pet friendly!

Jul 2 – 9

Loft in Peterborough

4.96 out of 5 average rating, 267 reviews

1850 Waterfall Mill-Loft Style Chic

IMMACULATE COUNTRY HOME W/ FAST WiFi in fresh air New Hampshire. Snuggled in on a quiet street, yet steps away from DOWNTOWN, two "Mini Whole Food" markets! State-of-the-art gourmet kitchen fleshed out with organic spices, wares for entertaining, and other luxuries such as a rReverse Osmosis drinking faucet. Stunning sunlit water views and soothing water sounds! Beautiful antique furnishings and marble finishes add to the unique beauty of this New England home.

Jun 4 – 11

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 124 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

Feb 3 – 10

Apartment in Keene

4.95 out of 5 average rating, 133 reviews

"Up Top" Downtown Rooftop Apartment

This spacious (nearly 1,300 sq ft) rooftop apartment has the best of both worlds - a serene, quiet setting and a convenient downtown location. Walk to restaurants, bars, shopping and more. Free on-site parking for up to two vehicles. *Please note if you are booking after March 2024, we will be making some updates to the space. It will still accommodate 4 guests and amenities will be the same, if not better!*

Dec 18 – 25

Cabin in Harrisville

4.95 out of 5 average rating, 131 reviews

Trailside Cottage in charming Harrisville, NH

Hike, bike, cross-country, snowshoe, or just inhale/exhale and enjoy the peace and quiet of a classic New England escape. Welcome to Trailside Cottage, a charming getaway in Harrisville, NH. Recently converted into a cozy space for two. It sits alongside one of the many trails in the Harrisville area, and is accessible to all of the amenities in the Monadnock Region.

Feb 14 – 21

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Other great vacation rentals in Cheshire County

Cabin in Fitzwilliam

4.84 out of 5 average rating, 108 reviews

Cozy Log Cabin Mountain Views

May 30 – Jun 6

Cabin in Stoddard

4.98 out of 5 average rating, 160 reviews

Cozy Comfort on 250 Acre Private Estate

Dec 25 – Jan 1

Guest suite in Peterborough

4.99 out of 5 average rating, 118 reviews

Meadow View

Jul 22 – 29

Apartment in Keene

5.0 out of 5 average rating, 28 reviews

Cozy Downtown Keene Private Apartment

May 26 – Jun 2

Home in Keene

5.0 out of 5 average rating, 12 reviews

Little House with Lots to Offer

Aug 14 – 21

Tiny home in Brattleboro

4.94 out of 5 average rating, 34 reviews

Sweet Vermont Tiny Home Get Away

Oct 28 – Nov 4

Apartment in Nelson

4.88 out of 5 average rating, 81 reviews

Swiss Chalet Family Retreat!

Jul 30 – Aug 6

Apartment in Keene

4.9 out of 5 average rating, 69 reviews

Apartment in Keene

Jun 28 – Jul 5

Destinations to explore