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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 rustic cabin with a covered porch, a small shed, and outdoor seating.

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, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $128
CA $223 total
includes taxes & fees
Oct 25 - Oct 26
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A two-story house with a front porch, a staircase, and a small garden area.

2. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (9 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is CA $239
CA $292 total
includes taxes & fees
Oct 19 - Oct 20
Central Large 2-bedrooms with office in Keene
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.
The price is CA $264
CA $414 total
includes taxes & fees
Oct 20 - Oct 21
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A lakeside park with picnic tables and a concrete walkway.

4. 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 $78
CA $116 total
includes taxes & fees
Oct 17 - Oct 18
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.

5. 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)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is CA $123
CA $210 total
includes taxes & fees
Oct 26 - Oct 27
Yurt Oasis in the woods of Hinsdale, NH
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

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

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property . Clean house. Attention to detail in every part of the house."
United States
Michael
The price is CA $338
CA $420 total
includes taxes & fees
Oct 18 - Oct 19
"Pondlife" - Waterfront home in a peaceful, wooded setting.
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, (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 CA $272
CA $690 total
includes taxes & fees
Oct 19 - Oct 20
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A wooden deck with outdoor furniture, a white door, and windows.

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 $277
CA $561 total
includes taxes & fees
Oct 28 - Oct 29
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

9. 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 $293
CA $531 total
includes taxes & fees
Oct 22 - Oct 23
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.

10. 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)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is CA $298
CA $445 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Tiny House on Main Street. Fully Renovated.
A cabin with a covered porch, large windows, and snow-covered ground.

11. 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.
The price is CA $271
CA $441 total
includes taxes & fees
Oct 19 - Oct 20
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.

12. 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.
The price is CA $337
CA $522 total
includes taxes & fees
Oct 20 - Oct 21
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

13. 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 $479
CA $902 total
includes taxes & fees
Oct 18 - Oct 19
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
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 $850
CA $1,330 total
includes taxes & fees
Nov 15 - Nov 16
2 Cabins & Sauna on Lake Monomonac
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
9.2 out of 10, Wonderful, (25 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is CA $172
CA $297 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Cabin in a rural setting #12 in Temple NH
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

16. 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, (47 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $166
CA $290 total
includes taxes & fees
Oct 18 - Oct 19
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

17. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is CA $113
CA $159 total
includes taxes & fees
Oct 20 - Oct 21
Cozy Vermont Tiny Home Get Away
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

18. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is CA $178
CA $301 total
includes taxes & fees
Oct 18 - Oct 19
Lovely 2nd Floor Apartment
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 $102
CA $313 total
includes taxes & fees
Nov 4 - Nov 5
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 $227
CA $409 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
"Our room was amply sized to fit our family, including our pack-n-play fro our toddler. The provided breakfast was great the three morning we were there. The indoor pool was cold during our stay, and appeared to be undergoing some renovation. Otherwise it was a great stay."
Tim 3-night trip
Posted 15 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 $297 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.