Holiday Rentals in Cheshire County

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Featured Holiday Rentals in Cheshire County

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Outdoor dining

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

10.0 out of 10, Exceptional, (6)
"Beautiful property and great a host! My boys loved getting up early and fishing into the night! Perfect get away from the hustle and bustle of every day life. If you love nature this is a great place. Lots to explore! We had a GREAT also caught some good size BASS. Definitely will be back again. Thanks tons, The Gallant Family "
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (7)
"My husband and I had a great weekend at Owl's Nest. The space was small, but cozy and the space was so well thought out in every way. It was meticulously clean, the lighting was magical, the hot tub was so cozy, and the host was very thoughtful in providing k-cups and local syrup and honey! Even though the cabin is on the same property as another house, it felt secluded. If you stay at this cabin, I definitely recommend going to L.A. Burdick in Walpole and having dinner at Wunderbar in Bellows...
The price is €292
includes taxes & fees
14 Sept - 15 Sept
Owl's Nest Treehouse
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

10.0 out of 10, Exceptional, (5)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Interior

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (4)
"We had a wonderful stay."
The price is €494
includes taxes & fees
11 Sept - 12 Sept
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
3 bedrooms, Internet, bed sheets

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (26)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Private Beach And Mountain Lake Home
Miscellaneous

Private Beach And Mountain Lake Home

9.6 out of 10, Exceptional, (121)
"We thoroughly enjoyed our stay at the Cabin in the Sky. We had a very relaxing stay."
Private Beach And Mountain Lake Home
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is €176
includes taxes & fees
14 Sept - 15 Sept
Lovely 2nd Floor Apartment
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (42)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Happy Place On Lake Sunapee - 10 minutes from the ski resort
Outdoor dining

Happy Place On Lake Sunapee - 10 minutes from the ski resort

9.6 out of 10, Exceptional, (51)
"This property is well appointed, cheerful and nicely located on the lake. My wife and I and another couple enjoyed the lake atmosphere with kayaking, sightseeing and shopping. Thanks to the owners for providing our perfect getaway."
Happy Place On Lake Sunapee - 10 minutes from the ski resort
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Interior

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

10.0 out of 10, Exceptional, (6)
"We had the most amazing stay at Leah and Chris’s beautiful home! From the moment we arrived, we were blown away by how clean, spacious, and thoughtfully stocked the house was—it truly had everything we could possibly need and more.Our group of 12 (including young kids and dogs!) had tons of space to spread out comfortably, and every single bed was super cozy. The huge yard was perfect for lawn games, which were conveniently provided, and we spent hours outside enjoying the privacy and peaceful...
The price is €973
includes taxes & fees
10 Sept - 11 Sept
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (39)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Exterior

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

9.6 out of 10, Exceptional, (23)
"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "
Charming Lake Sunapee & Mt. Sunapee Ski Cabin
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (7)
"Everything was really nice! The house was great and the whole place lovely. Great location! The manager was really helpful and easy to get in touch with. He was able to help us with all of our questions. The conditions of the mountain were really good. Wonderful stay! "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (57)
"Stayed twice would stay again"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Exterior

Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!

10.0 out of 10, Exceptional, (25)
"Clean cute cabin close to ski area well equipped with good living space. "
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Quiet private pond getaway
Property grounds

Quiet private pond getaway

9.4 out of 10, Exceptional, (15)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is €297
includes taxes & fees
19 Sept - 20 Sept
Family Friendly Hilltop House In Putney Vermont
Spectacular Log Home with Private Lake Access
TV, books, music library, video library

Spectacular Log Home with Private Lake Access

10.0 out of 10, Exceptional, (104)
"The property was great! Very clean and had everything we needed to cook meals and just relax. Lake was nice but it was a little chilly over the weekend. The hosts left some muffins, cookies, fruit and some beverages which was we though was a nice touch."
Spectacular Log Home with Private Lake Access
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, table football, ping pong

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (52)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Private kitchen

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

10.0 out of 10, Exceptional, (16)
"We loved our weekend experience at the Hideaway! "
The price is €393
includes taxes & fees
10 Sept - 11 Sept
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
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

Find out more about Cheshire County

Find out more about Cheshire County

Holiday Homes in Cheshire County

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