A large rock with carved faces and a river in the background.

Holiday Rentals in Cheshire County

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Our top choices for Cheshire County holiday rentals

A lake surrounded by trees, with a wooden deck leading to a white railing.

1. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (7 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is €254
includes taxes & fees
2 Nov - 3 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

2. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is €314
includes taxes & fees
2 Nov - 3 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

3. 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, (5 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 €416
includes taxes & fees
2 Nov - 3 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

4. 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, (20 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is €141
includes taxes & fees
2 Nov - 3 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

5. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"This was a perfect place to stay for my solo trip into town for a family wedding. The host was incredibly responsive and friendly and I'd recommend this place to anyone visiting the area!"
United States
David W.
The price is €273
includes taxes & fees
2 Nov - 3 Nov
Cozy Tiny House on Main Street. Fully Renovated.
A wooden cabin with a gabled roof, multiple windows, and a front porch.

6. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
2 Cabins & Sauna on Lake Monomonac
A sunlit room with a large window, a bench, and a sofa.

7. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is €328
includes taxes & fees
2 Nov - 3 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A red house with a stone pathway leading to it, surrounded by autumn foliage.

8. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (27 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is €617
includes taxes & fees
2 Nov - 3 Nov
Cobb Meadow House: Cozy 5 Bedroom Retreat
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

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

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (6 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 €535
includes taxes & fees
2 Nov - 3 Nov
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A lakeside park with picnic tables and a concrete walkway.

10. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is €68
includes taxes & fees
2 Nov - 3 Nov
2 private mountain RV pads for rent. Full hook ups
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

11. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
The price is €130
includes taxes & fees
2 Nov - 3 Nov
Yurt Oasis in the woods of Hinsdale, NH
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

12. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (48 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is €160
includes taxes & fees
18 Nov - 19 Nov
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

13. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is €218
includes taxes & fees
2 Nov - 3 Nov
Lovely 2nd Floor Apartment
A garden with a wooden pergola, purple flowers, and a river view.

14. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is €243
includes taxes & fees
2 Nov - 3 Nov
Family Friendly Hilltop House In Putney Vermont
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

15. Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH
Temple
9.0 out of 10, Wonderful, (26 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is €198
includes taxes & fees
2 Nov - 3 Nov
Cozy Cabin in a rural setting #12 in Temple NH
A modern living room with a fireplace, a mounted TV, and a leather couch.

16. 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, (28 reviews)
"Great place to stay. The cabin was nice and cozy. Quiet and remote area to relax"
United States
Anthony R.
The price is €235
includes taxes & fees
8 Nov - 9 Nov
Cozy Cabin in a Rural Setting #16 near Temple,NH
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

17. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is €236
includes taxes & fees
9 Nov - 10 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A house with a staircase leading to a porch, surrounded by snow and string lights.

18. 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, (13 reviews)
"Nice place"
United States
Tom
The price is €247
includes taxes & fees
2 Nov - 3 Nov
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A black-framed door with a glass panel, leading into a hallway with wooden flooring and white walls.

19. Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (13 reviews)
"The experience was exemplary, and I would certainly consider staying at this property again should my travels return me to New Hampshire."
United States
Anghy
The price is €219
includes taxes & fees
2 Nov - 3 Nov
Cozy Cabin in a Rural setting-14
A conservatory with a view of a lake surrounded by trees. Inside, there are two sofas facing the glass walls.

20. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Bennington
10.0 out of 10, Exceptional, (16 reviews)
"Very cozy house Perfect for all family trip Very clean "
United States
Marcin W.
The price is €344
includes taxes & fees
18 Nov - 19 Nov
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

8/10 Good
"good"
Ralph 1-night trip
Posted 12 hours ago
Comfort Inn & Suites Brattleboro I-91

Find out more about Cheshire County

Holiday Homes in Cheshire County

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