
Holiday rentals in Cheshire County
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Top-rated holiday rentals in Cheshire County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Cheshire County
Guest favourite

Home in Keene
4.92 out of 5 average rating, 50 reviewsLittle House with Lots to Offer
AmyRating, 5 stars3 weeks ago
Julie was a great host. The house is tucked away so it’s a bit hard to find but her directions helped us find it easily. The yard was great for the dogs and the dogs loved the beds and dog toys. The house was clean and had everything we needed. We were very happy to be able to stay in a dog friendly place so we could see family for Easter. Thank you!
Superhost

Home in Keene
4.75 out of 5 average rating, 4 reviews2 Master Suites, Hot Tub, Walking to Downtown.
StephenRating, 5 stars9 months ago
Behind an unassuming exterior façade, the interior was truly remarkable from an interior design and furnishing perspective. Not only were the furniture, linens and glassware spectacular, The overall result was a beautiful and tranquil retreat. We were super impressed and would love to return.
Top guest favourite

Home in Brattleboro
4.94 out of 5 average rating, 122 reviewsSpacious Brattleboro home on river, walk to town
DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Top guest favourite

Farm stay in Walpole
4.83 out of 5 average rating, 23 reviewsCottage with outdoor space 20 min to Brattleboro
LaurieRating, 5 stars1 week ago
We totally enjoyed our stay at Caitlin’s. The Kilburn cottage at the Valley Farm was just beautiful. So peaceful with a lovely flower garden. We enjoyed the homemade blueberry cake she left to welcome our visit. Dinner at the Hungry Diner was also so enjoyable. We were only there for one night to attend our son’s graduation in Keene but would definitely stay here again or visit the Inn next door.
Top guest favourite

Home in Walpole
4.99 out of 5 average rating, 74 reviewsCharming, Large House in Walpole NH /VT. Border
HeatherRating, 5 stars2 months ago
Karen's place was just what we were hoping for, a cozy historic home with plenty of space to spread out and relax after a long drive. Absolutely would stay here again. The details: well stocked kitchen, hot showers with good water pressure, comfy beds, cosy furniture, quiet amd peaceful stay.
Top guest favourite

Home in Hillsboro
4.98 out of 5 average rating, 42 reviewsYour private lake retreat awaits
GarmaiseRating, 5 stars2 months ago
This house is absolutely gorgeous and also feels very relaxing at the same time. The views from the house of the lake literally take your breath away. Ewa is very responsive and kind. She accommodated us in ways she really didn't need to and we appreciated that so much. Wifi is great at this house, if you need to work or have meetings. However, you may have issues with reception (depending on your carrier) in the area so be sure to write down directions before going! Also the street is really just the driveway and it's not marked so be sure to follow GPS to know when you have arrived! We would stay here again in a heartbeat. It's a great house for 2 families to stay together! And the basement with the pool table and ping pong - wow- what a bonus!!

Cottage in Rindge
4.78 out of 5 average rating, 18 reviewsSecluded Lake Cottage Perfect for Family Fun!
Maureen and John and ThomasRating, 5 stars22 months ago
This was a cozy, peaceful getaway for a quiet family retreat. The lake is a special treasure, with boats, life jackets, and other amenities on site. We felt right at home and well taken care of at this quaint forest residence. Great communication and thoughtful caretaking :)
Guest favourite

Cottage in Keene
4.83 out of 5 average rating, 66 reviewsHeron Cove Cottage: A Sweetwater Stay
GretchenRating, 5 stars1 month ago
Was a very nice peaceful place for a few weeks
Destinations to explore
- Rentals with a kayak Cheshire County
- House rentals Cheshire County
- Rentals with a firepit Cheshire County
- Rentals with a washing machine and dryer Cheshire County
- Beachfront rentals Cheshire County
- Rentals with a hot tub Cheshire County
- Pet-friendly rentals Cheshire County
- Rentals with pools Cheshire County
- Flat rentals Cheshire County
- Rentals with lake access Cheshire County
- Rentals with outdoor seating Cheshire County
- Farm stay rentals Cheshire County
- Rentals with a fireplace Cheshire County
- Rentals with a patio Cheshire County
- Rentals with breakfast Cheshire County
- Family-friendly rentals Cheshire County
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- Stratton Mountain
- Okemo Mountain Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Pats Peak Ski Area
- Ragged Mountain Resort
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Aaronap Cellars
- Mount Sugarloaf State Reservation
- Manchester Country Club - NH
- Nashoba Valley Ski Are
- Bear Brook State Park
- Ekwanok Country Club
- Hooper Golf Course
- Nashua Country Club
- The Shattuck Golf Club
- Baker Hill Golf Club
- Veterans Memorial Recreation Area Ski Hill
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Stump Sprouts Ski Touring Center
- Clarksburg State Park