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Cheshire County Vacation Rentals

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Top Cities in Cheshire County

A group of hikers on rocky terrain with dense forest in the background.
Vacation RentalsVacation Rentals

Jaffrey

Jaffrey

Our top choices for Cheshire County vacation rentals

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

1. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
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 CA $333
CA $394 total
includes taxes & fees
Oct 31 - Nov 1
"Pondlife" - Waterfront home in a peaceful, wooded setting.
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 CA $288
CA $524 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $268
CA $670 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $133
CA $228 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $294
CA $440 total
includes taxes & fees
Oct 31 - Nov 1
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
The price is CA $796
CA $1,262 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $273
CA $523 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $587
CA $968 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $472
CA $888 total
includes taxes & fees
Oct 31 - Nov 1
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A grassy field with trees and a red building in the background.

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 CA $77
CA $114 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $130
CA $216 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $145
CA $267 total
includes taxes & fees
Nov 18 - Nov 19
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a 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 CA $214
CA $347 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $204
CA $396 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $169
CA $293 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $215
CA $337 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $224
CA $399 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $315
CA $401 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $197
CA $326 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $269
CA $551 total
includes taxes & fees
Nov 18 - Nov 19
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

Gardner Inn

Gardner Inn

8/10 Good
"The room overall was ok, but the curtains were absolutely disgustingly dirty. The staff was very nice and overall, the room was fine. But looking at the dirty curtains was a real turn off to me."
Mary Ann 1-night trip
Posted 1 day ago
Gardner Inn

Find out more about Cheshire County

Everything you need to know about Cheshire County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cheshire County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire County vacation rentals we have selected for you start as low as CA $114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire County rentals

At Expedia, we put the best Cheshire County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheshire County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.