Find Vacation Homes in Cheshire County, NH from $201

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In one month
In two months
In three months

Vacation Homes in Cheshire County

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (38)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
$180 nightly
The price is $201
Oct 19 - Oct 20
Total with taxes and fees
Lovely 2nd Floor Apartment

Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

10.0 out of 10, Exceptional, (135)
"This was our second time renting this property for a quick ski trip. The property is spacious, and well appointed. It really offers everything you need for a relaxing ski vacation. Love the game room and the space."
Spacious Three-level Home , Well-Furnished, Fun Playroom, Minutes to Mt. Snow

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

9.0 out of 10, Wonderful, (27)
"We were only 4 people, and it felt huge. The cabin is nice, but does show some aging here and there. Nothing that was an actual issue, though. The property with the pond, the fire pit area and the little playground is absolutely gorgeous, though. The cabin offers plenty of space with 4.5 separate sleeping areas (there is a large futon in the game room that could be used in an emergency, I guess). The livingroom/kitchen area is very spacious with great views. Will definitely consider this for...
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Private Beach And Mountain Lake Home

9.6 out of 10, Exceptional, (123)
"I loved the house with so many bits of history of times past. It was also nice that it had just about anything you could possibly need which makes packing less stressful. I would have loved to k ow more about the artwork that adorns the walls and yard. I felt very much at peace while there."
Private Beach And Mountain Lake Home

Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c

10.0 out of 10, Exceptional, (3)
"Great family space. Comfortable furniture, well-stocked kitchen, close to restaurants. A/C units worked well."
Beautiful house w/ mountain views, fireplace, balcony, bbq, gameroom, w/d, a/c

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (61)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

16 ppl 2 hot tubs, game room, fire pit

9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
$555 nightly
The price is $602
Oct 22 - Oct 23
Total with taxes and fees
16 ppl 2 hot tubs, game room, fire pit

The Green Mountain Chapel // Old Church repositioned into 3 BR

2.0 star property
10.0 out of 10, Exceptional, (18)
"This is a really beautiful place to stay. The kitchen has pretty much very your would need for a stay, and the host leaves little extras for you. Absolutely would stay here again."
The Green Mountain Chapel // Old Church repositioned into 3 BR

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

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.

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (41)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

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

Inviting Condo w Fire Place & Hot Tub

9.4 out of 10, Exceptional, (6)
"We stayed for two nights and enjoyed our time here. We didn't get to use the hot tub, but we did use the fireplace. The condo was nice and cozy, and we would definitely stay here again."
Inviting Condo w Fire Place & Hot Tub

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (85)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (20)
"Nice house in a nice location. "
$367 nightly
The price is $398
Oct 27 - Oct 28
Total with taxes and fees
Downtown Hot Tub Escape

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (225)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Spacious Riverfront Home 7 Minutes to Stratton!

10.0 out of 10, Exceptional, (33)
"Perfect house for a few families to gather and have fun. "
Spacious Riverfront Home 7 Minutes to Stratton!

Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains

9.0 out of 10, Wonderful, (68)
"My husband and i enjoyed our stay. The cabin was very clean and comfortable. We would definitely rent it again."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

9.8 out of 10, Exceptional, (25)
"Enjoyed our time together at this home and in this area of Vermont."
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire County Hotel Reviews

Find out more about Cheshire County

Find out more about Cheshire County

Booking Tips to Find the Best Cheshire County Vacation Homes


How much does it cost to rent a vacation home in Cheshire County?

You can find incredible Cheshire County vacation homes for all types of budgets: between $201 and $602 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Cheshire County?

If you are looking for a great deal on your vacation home in Cheshire County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Cheshire County?

There are 679 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Cheshire County?

Begin by entering your trip dates to see what type of Cheshire County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Cheshire County?

Booking Cheshire County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Cheshire County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Cheshire County along with your vacation property, into a Cheshire County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Cheshire County Vacation Homes information

Number of reviews
1,005
Accommodation
679 Vacation Homes
Lowest Price
$201
Highest Price
$602

Explore a world of travel with Expedia

Explore a world of travel with Expedia