
Vacation rentals in Cheshire County
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Top-rated vacation rentals in Cheshire County
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Cheshire County vacation rentals
Other great vacation rentals in Cheshire County
Top guest favorite

Cottage in Nelson
4.99 out of 5 average rating, 123 reviewsCozy and Romantic Granite Lake Cottage Getaway
Guest favorite

Cabin in Rindge
4.93 out of 5 average rating, 123 reviewsWaterfront Log Home on Lake Contoocook
Guest favorite

Home in Keene
4.92 out of 5 average rating, 50 reviewsLittle House with Lots to Offer
Superhost

Home in Keene
4.75 out of 5 average rating, 4 reviews2 Master Suites, Hot Tub, Walking to Downtown.
Top guest favorite

Home in Brattleboro
4.94 out of 5 average rating, 122 reviewsSpacious Brattleboro home on river, walk to town
Top guest favorite

Farm stay in Walpole
4.83 out of 5 average rating, 23 reviewsCottage with outdoor space 20 min to Brattleboro
Top guest favorite

Home in Walpole
4.99 out of 5 average rating, 75 reviewsCharming, Large House in Walpole NH /VT. Border
Top guest favorite

Home in Hillsboro
4.98 out of 5 average rating, 42 reviewsYour private lake retreat awaits
Destinations to explore
- Pet-friendly rentals Cheshire County
- Rentals with a washer and dryer Cheshire County
- Rentals with a patio Cheshire County
- Farmstay rentals Cheshire County
- Rentals with a hot tub Cheshire County
- Beachfront rentals Cheshire County
- Rentals with a fireplace Cheshire County
- Rentals with a fire pit Cheshire County
- Rentals with pools Cheshire County
- Apartment rentals Cheshire County
- Rentals with breakfast Cheshire County
- Rentals with lake access Cheshire County
- Rentals with outdoor seating Cheshire County
- Rentals with a kayak Cheshire County
- Kid-friendly rentals Cheshire County
- House rentals Cheshire County
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Manchester Country Club - NH
- Aaronap Cellars
- Mount Sugarloaf State Reservation
- Bear Brook State Park
- Nashoba Valley Ski Are
- Dorset Field Club
- Clarksburg State Park
- Ekwanok Country Club
- Nashua Country Club
- The Shattuck Golf Club
- Hooper Golf Course
- Mount Tom State Reservation
- Fox Run Golf Club
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes