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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 yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

1. 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 $126
CA $220 total
includes taxes & fees
Nov 2 - Nov 3
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A grassy field with trees and a red building in the background.

2. 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 30 - Oct 31
2 private mountain RV pads for rent. Full hook ups
A house by a lake with a dock and a boat.

3. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Jim was a great host very friendly and welcoming, the cabin is in the perfect spot on the lake and we were able to see a fireworks show directly on the dock, thank you !"
United States
clifford t.
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A lake surrounded by trees, with a wooden deck leading to a white railing.

4. "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 $334
CA $414 total
includes taxes & fees
Oct 30 - Oct 31
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

5. 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 $289
CA $525 total
includes taxes & fees
Nov 1 - Nov 2
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

6. 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 $441 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Tiny House on Main Street. Fully Renovated.
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

7. 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 $269
CA $672 total
includes taxes & fees
Nov 2 - Nov 3
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A sunlit room with a large window, a bench, and a sofa.

8. 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 $549 total
includes taxes & fees
Nov 2 - Nov 3
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A cabin with a covered porch, large windows, and snow-covered ground.

9. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

10. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 $123
CA $209 total
includes taxes & fees
Oct 29 - Oct 30
Yurt Oasis in the woods of Hinsdale, NH
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

12. 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 $473
CA $890 total
includes taxes & fees
Oct 30 - Oct 31
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A red house with a stone pathway leading to it, surrounded by autumn foliage.

13. 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 $671
CA $1,123 total
includes taxes & fees
Nov 1 - Nov 2
Cobb Meadow House: Cozy 5 Bedroom Retreat
A wooden cabin with a gabled roof, multiple windows, and a front porch.

14. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is CA $797
CA $1,265 total
includes taxes & fees
Nov 15 - Nov 16
2 Cabins & Sauna on Lake Monomonac
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

15. 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 $143
CA $261 total
includes taxes & fees
Oct 29 - Oct 30
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

16. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (1 review)
"Cozy, clean and peaceful spot! Host was responsive and helpful."
United States
Maggie G.
The price is CA $101
CA $146 total
includes taxes & fees
Nov 10 - Nov 11
Cozy Vermont Tiny Home Get Away
A bedroom with a bed, a bedside table, and a nightstand. There is a window with blinds and a door leading to the outside.

17. Cozy Cabin in a rural setting #10 In Temple, NH

Cozy Cabin in a rural setting #10 In Temple, NH
Temple
9.0 out of 10, Wonderful, (20 reviews)
"Great place"
United States
Ann S.
The price is CA $154
CA $274 total
includes taxes & fees
Oct 30 - Oct 31
Cozy Cabin in a rural setting #10 In Temple, NH
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

18. 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 $170
CA $293 total
includes taxes & fees
Oct 29 - Oct 30
Cozy Cabin in a rural setting #12 in Temple NH
A blue house with a porch, a wooden bench, and a door.

19. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is CA $91
CA $292 total
includes taxes & fees
Nov 3 - Nov 4
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

20. 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 $403 total
includes taxes & fees
Nov 3 - Nov 4
Wellness Getaway with a Personal Sauna, and Private River Beach!
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
"The room was nice and clean. Recent renovation was done"
Bradley 1-night trip
Posted 2 hours ago
Comfort Inn & Suites Brattleboro I-91

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.