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Cheshire County Holiday Rentals

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Our top choices for Cheshire County holiday rentals

Exterior detail
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cabin in Fitzwilliam

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is AU$317
includes taxes & fees
16 Dec - 17 Dec
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Owl's Nest Treehouse

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (14)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
The price is AU$511
includes taxes & fees
17 Dec - 18 Dec
Owl's Nest Treehouse
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AU$380
includes taxes & fees
16 Dec - 17 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor spa tub
Downtown Hot Tub Escape

Holiday Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is AU$425
includes taxes & fees
16 Dec - 17 Dec
Downtown Hot Tub Escape
Smart TV, fireplace, printers
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cottage in Rindge

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
10.0 out of 10, Exceptional, (22)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is AU$560
includes taxes & fees
16 Dec - 17 Dec
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Terrace/patio
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
The price is AU$846
includes taxes & fees
16 Dec - 17 Dec
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Fridge, microwave, oven, stovetop
Charming Home Walk to Downtown!

Holiday Home in Keene

Charming Home Walk to Downtown!
10.0 out of 10, Exceptional, (2)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is AU$943
includes taxes & fees
6 Jan - 7 Jan 2026
Charming Home Walk to Downtown!
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Holiday Home in Stoddard

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
10.0 out of 10, Exceptional, (1)
"Place was clean, cozy & very relaxing.. accommodating & communicative host provided us with necessary info for great week! Beautiful lake & landscape was great viewing during surprise snowstorm! Our Thanksgiving week was wonderful as we enjoyed lovely, quiet area in spacious 4 bdrm/2 bath home! Will definitely consider returning"
United States
Jeannie M.
The price is AU$701
includes taxes & fees
16 Dec - 17 Dec
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Apartment in Keene

Entire private apartment suite in home with own entrance, views and private gym.
The price is AU$558
includes taxes & fees
16 Dec - 17 Dec
Entire private apartment suite in home with own entrance, views and private gym.
Exterior
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is AU$388
includes taxes & fees
15 Jan - 16 Jan 2026
Wellness Getaway with a Personal Sauna, and Private River Beach!
Outdoor pool, a heated pool
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is AU$443
includes taxes & fees
6 Jan - 7 Jan 2026
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior detail
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Apartment in Peterborough

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
9.8 out of 10, Exceptional, (30)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is AU$242
includes taxes & fees
18 Dec - 19 Dec
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Property grounds
Cottage beside a waterfall

Cottage in Wilton

Cottage beside a waterfall
9.8 out of 10, Exceptional, (10)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
United States
Marcella J.
The price is AU$437
includes taxes & fees
17 Dec - 18 Dec
Cottage beside a waterfall
Family Cabin, 2 Bedrooms, Mountain View | Living room
Brook Road Cabin

Cottage in Goshen

Brook Road Cabin
3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin
Exterior
Modern 3BR Near FSU • 15 Min to Wachusett

Apartment in Fitchburg

Modern 3BR Near FSU • 15 Min to Wachusett
10.0 out of 10, Exceptional, (12)
"Wonderful place to stay. Everything was very clean, comfortable, and spacious, with a warm, welcoming feel. I highly recommend the place to stay. "
United States
Catherine
The price is AU$507
includes taxes & fees
27 Dec - 28 Dec
Modern 3BR Near FSU • 15 Min to Wachusett
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
8.8 out of 10, Excellent, (3)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is AU$313
includes taxes & fees
16 Dec - 17 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is AU$305
includes taxes & fees
16 Dec - 17 Dec
Lovely 2nd Floor Apartment
Interior
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
The price is AU$548
includes taxes & fees
16 Dec - 17 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Property grounds
River Room overlooking the waterfall

Apartment in Wilton

River Room overlooking the waterfall
10.0 out of 10, Exceptional, (3)
"Had a great time, the grounds are spectacular with the river waterfall in the background. The Bathroom was stunning. Had everything we needed. The bed was super comfy too. The screened-in porch was convenient, too."
United States
Romie G.
The price is AU$437
includes taxes & fees
17 Dec - 18 Dec
River Room overlooking the waterfall
Exterior
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

Chalet in West Dover

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is AU$817
includes taxes & fees
17 Dec - 18 Dec
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"The room was perfect, and the food was great "
Paul 1-night trip
Posted 17 hours ago
Keene Elm City 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$443 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.