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Holiday Rentals in Cheshire County

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Top Cities in Cheshire County

A snow-covered town with a prominent church and a mountain in the background.
Holiday RentalsHoliday Rentals

Fitzwilliam

Fitzwilliam

Our top choices for Cheshire County holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is €309
includes taxes & fees
3 Aug - 4 Aug
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Coffee/tea maker, fridge, microwave, oven

2. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is €407
includes taxes & fees
24 Aug - 25 Aug
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
TV, books

3. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
3 bedrooms

4. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is €283
includes taxes & fees
3 Aug - 4 Aug
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Terrace/patio

5. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (16 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is €154
includes taxes & fees
1 Sept - 2 Sept
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

6. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is €378
includes taxes & fees
3 Aug - 4 Aug
Large Farmhouse with expansive views, firepit 15 min north of Keene
Exterior

7. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (4 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is €579
includes taxes & fees
31 Aug - 1 Sept
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Exterior

8. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is €1,278
includes taxes & fees
20 Aug - 21 Aug
2 Cabins & Sauna on Lake Monomonac
Outdoor dining

9. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is €75
includes taxes & fees
3 Aug - 4 Aug
2 private mountain RV pads for rent. Full hook ups
Property grounds

10. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is €149
includes taxes & fees
3 Aug - 4 Aug
Yurt Oasis in the woods of Hinsdale, NH
Property grounds

11. Cozy Campfire Camper Retreat - Lake Nearby!

Cozy Campfire Camper Retreat - Lake Nearby!
Henniker
10.0 out of 10, Exceptional, (1 review)
"Excellent visit! Comfortable and the host was extremely helpful!"
United States
Nicholas
Cozy Campfire Camper Retreat - Lake Nearby!
Exterior

12. Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Dover
8.8 out of 10, Excellent, (3 reviews)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
The price is €801
includes taxes & fees
31 Aug - 1 Sept
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Interior

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is €181
includes taxes & fees
3 Aug - 4 Aug
Lovely 2nd Floor Apartment
Exterior

14. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (170 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is €311
includes taxes & fees
4 Aug - 5 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Smart TV

15. Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural Setting #16 near Temple,NH
Temple
9.4 out of 10, Exceptional, (23 reviews)
"I would stay here again."
United States
Ann M.
The price is €207
includes taxes & fees
3 Aug - 4 Aug
Cozy Cabin in a Rural Setting #16 near Temple,NH
Exterior

16. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (10 reviews)
"Nice place"
United States
Tom
The price is €251
includes taxes & fees
3 Aug - 4 Aug
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Family Cabin, 2 Bedrooms, Mountain View | Living room

17. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is €259
includes taxes & fees
3 Aug - 4 Aug
Brook Road Cabin
Property grounds

18. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
9.8 out of 10, Exceptional, (18 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is €258
includes taxes & fees
5 Aug - 6 Aug
Cottage beside a waterfall
Property grounds

19. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (62 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is €260
includes taxes & fees
10 Aug - 11 Aug
Family Friendly Hilltop House In Putney Vermont
House (2 Bedrooms) | Interior

20. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is €356
includes taxes & fees
5 Aug - 6 Aug
Hiking Trails On-site: Cozy Falls Brook Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire County Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Nice pool and jacuzzi! Co venison to restaurants and shops"
Mary 1-night trip
Posted 12 hours ago
Hampton Inn Brattleboro

Find out more about Cheshire County

Holiday Homes in Cheshire County

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