Cheshire County Holiday Rentals

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Top Cities in Cheshire County

Keene showing a city and a church or cathedral
Holiday RentalsHoliday Rentals

Keene

Keene

Top Holiday Rentals Destinations in Cheshire County

Our top choices for Cheshire County holiday rentals

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)
"Treehouse was just as the pictures and description portray. It was clean, quiet and peaceful. My wife and I stayed at the Owl's Nest Treehouse for just a quick one night get away. It was the perfect spot for some quiet time alone and a soak in the hot tub. The check in process was as simple as it gets, and the owners were very responsive to the few questions we asked. For dinner we went to Springfield VT (about a 30 min drive). You can probably find something a little closer, but Alstead...
The price is NZ$564
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 NZ$953
includes taxes & fees
15 Sept - 16 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, (122)
"We had a wonderful stay! The house was very clean and comfortable and the area is beautiful!"
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 NZ$338
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)
"We LOVED this place! The house was stocked with all of the essentials, including towels and linens. This made traveling there easier. The swimming area was great too!"
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 NZ$1,876
includes taxes & fees
1 Oct - 2 Oct
"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)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
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)
"really enjoyed our stay. Place would be much better if there was a microwave."
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 NZ$570
includes taxes & fees
18 Sept - 19 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 stay here. House was very tidy, property owner easy to communicate with, and location great right by the lake and mountain. There are also a few nice hikes nearby. "
The price is NZ$759
includes taxes & fees
14 Sept - 15 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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Was blown away by the suite. It even had a washer and dryer in it. Jetted bathtub and a night evening for our birthdays. We will return"
Gary 1-night trip
Posted 4 days ago
Pointe at Castle Hill Resort

Find out more about Cheshire County

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 favorite 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 depends 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 selected for you start as low as NZ$338 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia