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Cheshire County Holiday Rentals

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Top cities in Cheshire County

A street with a clock, red brick buildings, and autumn leaves.
Vacation Rentals

Keene

Keene

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Cheshire County holiday 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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AU$231
includes taxes & fees
11 Nov - 12 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A lake surrounded by trees, with a wooden deck leading to a white railing.

2. 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 AU$406
includes taxes & fees
9 Nov - 10 Nov
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

3. 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 AU$431
includes taxes & fees
9 Nov - 10 Nov
Cozy Tiny House on Main Street. Fully Renovated.
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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 AU$659
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 AU$515
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A sunlit room with a large window, a bench, and a sofa.

6. 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)
"Excellent property, really enjoyed this beautiful home."
United States
Susan G.
The price is AU$542
includes taxes & fees
9 Nov - 10 Nov
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

7. 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 AU$215
includes taxes & fees
9 Nov - 10 Nov
Yurt Oasis in the woods of Hinsdale, NH
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

8. 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 AU$886
includes taxes & fees
9 Nov - 10 Nov
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A red house with a stone pathway leading to it, surrounded by autumn foliage.

9. 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 AU$986
includes taxes & fees
9 Nov - 10 Nov
Cobb Meadow House: Cozy 5 Bedroom Retreat
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

10. 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, (49 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AU$218
includes taxes & fees
9 Nov - 10 Nov
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.

11. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is AU$141
includes taxes & fees
30 Nov - 1 Dec
Cozy Vermont Tiny Home Get Away
A black-framed door with a glass panel, leading into a hallway with wooden flooring and white walls.

12. 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 AU$338
includes taxes & fees
9 Nov - 10 Nov
Cozy Cabin in a Rural setting-14
A stone pathway leading to a large, multi-story building surrounded by trees and shrubs.

13. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
9.8 out of 10, Exceptional, (24 reviews)
"Welcome letter to cottage is rude! Nice little cottage. That’s about it! No instructions on checkout at all! Location is great! Highly recommend the Taco Time restaurant though in town!"
United States
Shane
The price is AU$397
includes taxes & fees
9 Nov - 10 Nov
Cottage beside a waterfall
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

14. 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 AU$307
includes taxes & fees
9 Nov - 10 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.

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, (28 reviews)
"Pet friendly, easy checkin, host was very responsive and flexible."
United States
fran f.
The price is AU$362
includes taxes & fees
9 Nov - 10 Nov
Cozy Cabin in a Rural Setting #16 near Temple,NH
A garden with a wooden pergola, purple flowers, and a river view.

16. 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 AU$387
includes taxes & fees
10 Nov - 11 Nov
Family Friendly Hilltop House In Putney Vermont
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 AU$405
includes taxes & fees
16 Nov - 17 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
A blue house with a porch, a wooden bench, and a door.

18. 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 AU$335
includes taxes & fees
9 Nov - 10 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

19. 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 AU$351
includes taxes & fees
9 Nov - 10 Nov
Lovely 2nd Floor Apartment
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

20. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is AU$570
includes taxes & fees
18 Nov - 19 Nov
Stunning Glass House nestled in the Vermont wilderness!
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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Find holiday rentals that suit your style

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Apartments
Apartments

Top Cheshire County Hotel Reviews

A dock extending into a lake with a grassy area in the foreground and trees in the background.
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
West Chesterfield

8/10 Good

Pleasant stay hotel was empty when we arrived but filled up a bit by evening.
Australia
Jen123
Reviewed August 30, 2014
Riverside Hotel, an Ascend Collection Hotel

Find out more about Cheshire County

Everything you need to know about Cheshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Cheshire County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Cheshire County holiday rentals we have chosen for you start as low as AU$141 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 holiday 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 holiday.

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.