190+ Rental Villas and Private Getaways in Cheshire County |
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  3. Cheshire County

Cheshire County Vacation Rentals & One Degree Stays Homes

About Cheshire County Vacation Rentals

There are more than 190 vacation rentals that are available in Cheshire County. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Cheshire County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Cheshire County, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Cheshire County. Places to stay near Cheshire County are 1100.1 ft² on average, with prices averaging US $369 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Cheshire County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Cheshire County

Type Count
Vacation Homes 90
Cottages 23
Holiday Apartments 13
Villas 2

Use these Quick Filters to Find a Vacation Rental in Cheshire County

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Cheshire County.

Weather in Cheshire County, NH

View the weather forecast for Cheshire County before booking your Cheshire County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Cheshire County, NH

OneDegreeStays offers a large selection of top attractions around Cheshire County. Research things to do on your vacation before you visit Cheshire County.


Keene State College
Spofford Lake
Asbury United Methodist Church
Monadnock State Park
Granite Gorge
Colonial Theatre
Madame Sherri Forest
Brentwood Golf Course
Madame Sherris Castle Ruins
Central Square
Cathedral of the Pines
Pete's Stand Vegetables
Rhododendron State Park
Chesterfield Gorge Natural Area
Jaffrey Civic Center
Stonewall Farm
Historical Society of Cheshire County
Cheshire Children's Museum
Unbridled Chocolates
Walpole Farmers Market
Walpole Artisans Cooperative
Alumni Field
Friendly Farm
The Fells
Wantastiquet Mountain
CC&H Framing / Pepper Pete's Hot Shop
Hooper Golf Club
Actors Theatre Playhouse
Pitcher Mountain
Walpole Artisans Cooperative

Other Places to Stay in Cheshire County, NH


Monadnock Region 235 Properties
Keene 162 Properties
Winchester 155 Properties
Fitzwilliam 92 Properties
Swanzey 53 Properties
Stoddard 44 Properties
Harrisville 42 Properties
Dublin 42 Properties
Jaffrey 38 Properties
Historic Main Street 37 Properties
Rindge 32 Properties
Walpole 31 Properties

Frequently Asked Questions About Cheshire County?

What are the top vacation rentals in Cheshire County?

There are a lot of options in Cheshire County. If you plan on staying in the Cheshire County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cheshire County:

How many vacation rentals have private pools in Cheshire County?

There are 2 vacation rentals with private pools near Cheshire County. Top-rated ODS homes that have access to a swimming pool include:

Which vacation homes in Cheshire County are best for families?

If you are looking for a family-friendly vacation home in Cheshire County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cheshire County:

How many onedegreestays vacation rentals are available in Cheshire County?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 190 in the Cheshire County area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Cheshire County. 


People Also Ask

There are 190 Cheshire County, NH Vacation Rentals

Recently Booked Vacation Rentals in Cheshire County