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Vacation Rentals in Cheshire County

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Top Cities in Cheshire County

Our top choices for Cheshire County vacation rentals

Cabin in Alstead

10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
$310 nightly
The price is $336
Dec 14 - Dec 15
Total with taxes and fees
Owl's Nest Treehouse

Mobile Home in Fitzwilliam

10.0 out of 10, Exceptional, (10)
"This house is amazing. "
United States
Amanda Q.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Vacation Home in Andover

9.0 out of 10, Wonderful, (29)
"Really nice house in a beautiful place. We had a great time. Plenty of space with multiple bedrooms and bathrooms are great. Great kitchen and grill made it easy to feed lots of people. Also lots of great things to do in the house already. One criticism for me was the screen doors. They were not all set in the rails and some of them had holes that let bugs in. It got a bit warm in the house during the day time with no air conditioning so it would’ve been better if the screen doors were...
United States
Dan T.
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Vacation Home in Dover

10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Camping in Dover

8.0 out of 10, Very Good, (2)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
$742 nightly
The price is $838
Dec 14 - Dec 15
Total with taxes and fees
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Cabin in Dover

2.0 star property
9.6 out of 10, Exceptional, (9)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
United States
Gregory G.
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Vacation Home in Weston

9.8 out of 10, Exceptional, (9)
"An absolutely incredible home and property for a week long end of summer vacation. The setting, atmosphere, decor and attention to detail were all top notch and we couldn’t have been happier. We particularly loved the layout and all of the amenities. This property is a true winner for any season, and we cannot wait to return for a winter retreat! "
United States
Chris L.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Vacation Home in Dover

10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
$1,176 nightly
The price is $1,328
Dec 10 - Dec 11
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Apartment in 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.
$227 nightly
The price is $256
Dec 16 - Dec 17
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11

Vacation Home in West Dover

8.2 out of 10, Very Good, (10)
"Lovely place for a large group of people."
United States
Nicole M.
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

Vacation Home in Washington

9.6 out of 10, Exceptional, (124)
"Just returned from a wonderful stay at this property. The house was clean and had everything you could need while on vacation. The pond was so clean and clear. We even saw a loon."
United States
Patricia K.
Private Beach And Mountain Lake Home

Vacation Home in Cavendish

8.8 out of 10, Excellent, (9)
"Close to skiing"
United States
Donna
Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing

Cabin in Londonderry

8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
$502 nightly
The price is $567
Dec 10 - Dec 11
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Chalet in Wilmington

9.4 out of 10, Exceptional, (42)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! "
United States
lizzie m.
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Villa in Dover

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
United States
Allison S.
The Birch. A Spacious Mansion 2 min from Mt. Snow!

Cabin in Chester

10.0 out of 10, Exceptional, (23)
"Loved being tucked away in the wilderness. Owners were very responsive. "
United States
Katy B.
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Cabin in Grafton

9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$327 nightly
The price is $366
Dec 15 - Dec 16
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Apartment in Dover

9.6 out of 10, Exceptional, (5)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
$451 nightly
The price is $510
Dec 10 - Dec 11
Total with taxes and fees
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Cabin in Westminster

10.0 out of 10, Exceptional, (23)
"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "
United States
Michael T.
$468 nightly
The price is $513
Dec 11 - Dec 12
Total with taxes and fees
Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn
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

Discover your perfect Cheshire County vacation rental with Expedia

How many vacation rentals are available in Cheshire County?


Expedia has plenty of vacation rentals to choose from in and around  Cheshire County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Cheshire County?


The selection of Cheshire County vacation rentals we have selected for you start as low as $256 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Cheshire County?


Vacation rentals in Cheshire County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Cheshire County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Cheshire County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Cheshire County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Cheshire County?


Find vacation rentals in Cheshire County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Cheshire County.  


What amenities are available in a vacation rental in Cheshire County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Cheshire County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Cheshire County?   


Everytime is a great time to head to Cheshire County! Staying in a Cheshire County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Cheshire County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Cheshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Cheshire County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Cheshire County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.