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.

Guest favorite

Apartment in Dublin

4.96 out of 5 average rating, 177 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.

Aug 31 – Sep 7

$96 per night
Guest favorite

Guest suite in Fitzwilliam

4.96 out of 5 average rating, 283 reviews

The Carriage House in Historic Fitzwilliam

Welcome to the Carriage House! Former site of the popular Hannah Davis House Bed and Breakfast, this gorgeous space is ready for your visit! Beautiful wood beams throughout, a cozy loft bedroom, and a completely separate entrance for privacy. Short rides to Rhododendron State Park, Mount Monadnock, Gap Mountain, the Cheshire Rail Trail, Laurel Lake, and many more outdoor activities year round. Walking distance to the town common in a town where little has changed and history is preserved.

Dec 22 – 29

$81 per night
Guest favorite

Cabin in Marlow

4.98 out of 5 average rating, 104 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.

Aug 23 – 30

$105 per night

Popular amenities for Cheshire County vacation rentals

Other great vacation rentals in Cheshire County

Guest favorite

Apartment in Putney

4.89 out of 5 average rating, 107 reviews

Hip & Cozy Storefront

Nov 23 – 30

$103 per night
Guest favorite

Cabin in Stoddard

4.98 out of 5 average rating, 157 reviews

Cozy Comfort on 250 Acre Private Estate

Apr 10 – 17

$209 per night
Superhost

Guesthouse in Fitzwilliam

4.86 out of 5 average rating, 331 reviews

Tranquil Guest House with Sauna

Dec 29 – Jan 5

$127 per night
Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 281 reviews

Private & Quiet Studio Apt. in Vermont

Jun 24 – Jul 1

$79 per night
Guest favorite

Cottage in Town of Rockingham

4.94 out of 5 average rating, 216 reviews

Peaceful Mountain Cottage

$98 per night
Guest favorite

Cottage in Keene

4.97 out of 5 average rating, 34 reviews

Heron Cove Cottage: A Sweetwater Stay

Nov 18 – 25

$116 per night
Guest favorite

Guest suite in Westminster

4.95 out of 5 average rating, 38 reviews

COZY FARMHOUSE SUITE

Dec 22 – 29

$93 per night
Guest favorite

Apartment in Keene

5.0 out of 5 average rating, 28 reviews

Cozy Downtown Keene Private Apartment

Jun 6 – 13

$84 per night
Guest favorite

Apartment in Keene

4.89 out of 5 average rating, 66 reviews

Apartment in Keene

May 30 – Jun 6

$113 per night
Superhost

Cabin in Putney

4.89 out of 5 average rating, 74 reviews

Cabin getaway in Southern Vermont

Mar 18 – 25

$115 per night
Guest favorite

Bungalow in Putney

4.96 out of 5 average rating, 27 reviews

Cozy paradise in Westminster West

Aug 22 – 29

$104 per night
Superhost

Apartment in Nelson

4.88 out of 5 average rating, 81 reviews

Swiss Chalet Family Retreat!

Oct 16 – 23

$128 per night

Destinations to explore