Holiday Rentals in Cheshire County

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Our top choices for Cheshire County holiday rentals

Exterior detail
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Fitzwilliam
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is €182
includes taxes & fees
17 Dec - 18 Dec
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Owl's Nest Treehouse

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
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 €293
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

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is €212
includes taxes & fees
17 Dec - 18 Dec
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor spa tub
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
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 €242
includes taxes & fees
18 Dec - 19 Dec
Downtown Hot Tub Escape
Smart TV, fireplace, printers
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
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 €321
includes taxes & fees
17 Dec - 18 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

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
The price is €486
includes taxes & fees
17 Dec - 18 Dec
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Fridge, microwave, oven, stovetop
Charming Home Walk to Downtown!

Charming Home Walk to Downtown!

Charming Home Walk to Downtown!
Keene
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 €541
includes taxes & fees
6 Jan - 7 Jan 2026
Charming Home Walk to Downtown!
Exterior
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
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 €403
includes taxes & fees
17 Dec - 18 Dec
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Interior
Entire private apartment suite in home with own entrance, views and private gym.

Entire private apartment suite in home with own entrance, views and private gym.

Entire private apartment suite in home with own entrance, views and private gym.
Keene
The price is €318
includes taxes & fees
29 Dec - 30 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!

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is €266
includes taxes & fees
9 Jan - 10 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

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
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 €243
includes taxes & fees
7 Jan - 8 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.

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, (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 €139
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 beside a waterfall

Cottage beside a waterfall
Wilton
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 €251
includes taxes & fees
23 Dec - 24 Dec
Cottage beside a waterfall
Family Cabin, 2 Bedrooms, Mountain View | Living room
Brook Road Cabin

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
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

Modern 3BR Near FSU • 15 Min to Wachusett

Modern 3BR Near FSU • 15 Min to Wachusett
Fitchburg
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 €306
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

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
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 €180
includes taxes & fees
21 Dec - 22 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
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 €175
includes taxes & fees
17 Dec - 18 Dec
Lovely 2nd Floor Apartment
Interior
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
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 €314
includes taxes & fees
17 Dec - 18 Dec
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Property grounds
River Room overlooking the waterfall

River Room overlooking the waterfall

River Room overlooking the waterfall
Wilton
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 €251
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

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
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 €469
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 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Cheshire County

Holiday Homes in Cheshire County

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