Vacation rentals in Cheshire County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cheshire County

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

Guest favorite

Apartment in Putney

4.89 out of 5 average rating, 107 reviews

Hip & Cozy Storefront

Ground-level historic storefront turned into a private, hip place to sleep. Nestled in the village of Putney, VT it is just a walk to restaurants, General Store, nature trails and Next Stage Theater-short drive to Putney School, Landmark College & The Greenwood School- huge bathtub, movie screen, kitchenette with fridge, handicap accessible. Can sleep 3 or more upon request. The ski resorts of Okemo, Mt. Snow, Magic Mountain, and Stratton are not far~ making Putney a perfect ski get-a-way spot.

Nov 9 – 16

R2,231 ZAR per night
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.

Sep 6 – 13

R2,088 ZAR 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.

Mar 18 – 25

R1,759 ZAR per night

Popular amenities for Cheshire County vacation rentals

Other great vacation rentals in Cheshire County

Guest favorite

Cabin in Stoddard

4.98 out of 5 average rating, 157 reviews

Cozy Comfort on 250 Acre Private Estate

Apr 10 – 17

R4,553 ZAR per night
Superhost

Guesthouse in Fitzwilliam

4.86 out of 5 average rating, 331 reviews

Tranquil Guest House with Sauna

Dec 31 – Jan 7

R2,766 ZAR per night
Guest favorite

Cottage in Town of Rockingham

4.94 out of 5 average rating, 217 reviews

Peaceful Mountain Cottage

R1,861 ZAR per night
Superhost

Home in Putney

4.84 out of 5 average rating, 118 reviews

Spacious Loft with View

May 17 – 24

R3,197 ZAR per night
Guest favorite

Cottage in Keene

4.97 out of 5 average rating, 34 reviews

Heron Cove Cottage: A Sweetwater Stay

Feb 23 – Mar 2

R2,547 ZAR per night
Superhost

Apartment in Nelson

4.88 out of 5 average rating, 81 reviews

Swiss Chalet Family Retreat!

Oct 16 – 23

R2,829 ZAR per night
Guest favorite

Guest suite in Westminster

4.95 out of 5 average rating, 38 reviews

COZY FARMHOUSE SUITE

Dec 23 – 30

R2,021 ZAR per night
Guest favorite

Apartment in Keene

4.89 out of 5 average rating, 66 reviews

Apartment in Keene

Apr 26 – May 3

R2,464 ZAR per night
Guest favorite

Apartment in Keene

5.0 out of 5 average rating, 28 reviews

Cozy Downtown Keene Private Apartment

Jun 6 – 13

R1,840 ZAR per night
Guest favorite

Farm stay in Stoddard

5.0 out of 5 average rating, 77 reviews

Upton Farm and Forest

May 8 – 15

R3,246 ZAR per night
Guest favorite

Bungalow in Putney

4.96 out of 5 average rating, 27 reviews

Cozy paradise in Westminster West

Aug 23 – 30

R2,270 ZAR per night
Guest favorite

Apartment in Jaffrey

4.93 out of 5 average rating, 60 reviews

Apartment in Historic Home

Oct 20 – 27

R2,230 ZAR per night

Destinations to explore