
Kid-friendly vacation rentals in Cheshire County
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Top-rated kid-friendly rentals in Cheshire County
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Popular amenities for Cheshire County kid-friendly rentals
Kid-friendly house rentals

Secluded lakefront vacation home
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy

Little House with Lots to Offer
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!

Amazing Lakefront Home with Pool- Tatum's Place
Great stay overall — just be mindful of seasonal comfort! We had a lovely time at this beautiful property — it’s well-maintained, peaceful, and has a lot of charm. The host was responsive and check-in was easy. Just a heads-up for future guests: the property has seasonal settings, so you’ll either get heat or A/C depending on the time of year, not both. It made things a bit uncomfortable during a weather transition, but manageable. Still, the beauty and uniqueness of the space definitely made up for it. Would recommend with that one caveat in mind!

The Brick House on Washington Street
Beautiful, historic home in a lovely neighborhood close to downtown Keene. Charming and cozy inside and out. Comfortable beds and furniture. Wonderful artwork by Ruth throughout her home. Large bright kitchen with everything you’d need to stay. Enjoyed the architecture and restaurants in Keene. Highly recommend Ruth’s home to stay in this area!

Spring Getaway: Kayak & Unwind by Highland Lake
Our stay at Angela's place was absolutely fantastic. The moment we walked in the home gave that warm cabin cozy feeling. We were impressed by the cleanliness and attention to detail. The place had everything we needed for a comfortable stay. Angela was incredibly responsive and helpful, and we would definitely stay here again!"

Charming, Large House in Walpole NH /VT. Border
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.

Lovely Brick Schoolhouse
Evelyn was a fantastic host, and her home was absolutely beautiful and spacious. I highly recommend this stay—there’s plenty to do in the area if you enjoy the outdoors, and I can’t wait to visit again!

Bright, Large, Spacious Family Home
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Family-friendly apartment rentals

Downtown Loft next to Distillery
What a great stay! We would definitely return. Everything was perfect.

Sunny New England Apartment
Great stay! Kristin and Marty were amazing hosts and were very responsive. The place was very comfortable and clean, and the little touches like seasonal decorations, bagels and cream cheese, and creamer for coffee were so nice! I would absolutely recommend this place for a stay in Keene.

Spacious First Floor of Historic House
Great place! Pleasant and comfortable interior, good plumbing, ample space, lovely landscaping and an easy walk to Jaffrey Town Center. This is an historic building. If you prefer staying at the Hilton, this place is not ideal. Nevertheless, if you want a unique and comfortable experience with a competent host you will have an enjoyable and one-of-a-kind experience.

Farm land view.
Our return trip was just as great as the first time there. The apartment was spotless, the furniture and bedding is very comfortable. Has everything we needed. It is in a beautiful location 10 minutes from Massachusetts and New Hampshire. We feel at home and very safe . Peter is a great host and communicates very quickly. Looking forward to another visit.

Stunning Studio in historic Downtown Bellows Falls
This space is lovely, warm and inviting. Very comfortable and a cool downtown location. Remy was an awesome host, responsive and helpful. Absolutely makes my list of places to come stay again.

Apartment on Main Street
Perfect stay for our short trip! Whitney is wonderful and so responsive!

Cozy, Private & Great location for exploring VT !
I really enjoyed the space. It was clean, free of clutter and very cozy. The bed was comfortable and included a desk for workspace. It was quiet and had all the amenities you would need. I loved the gas fireplace and outdoor patio. I plan to return to the apartment in the future and highly recommend this location. Mary (the host) was very friendly and helpful. I had a great stay!

Private Apartment with a Mt. view
Cold Comfort Farm offers a wonderful setting and view for anyone who wants a true New Hampshire experience. It reminded me of my youth growing up nearby. Jo was completely welcoming.
Destinations to explore
- Rentals with outdoor seating Cheshire County
- Beachfront rentals Cheshire County
- Rentals with a washer and dryer Cheshire County
- Pet-friendly rentals Cheshire County
- Apartment rentals Cheshire County
- Rentals with a kayak Cheshire County
- Rentals with a firepit Cheshire County
- Farmstay rentals Cheshire County
- House rentals Cheshire County
- Rentals with breakfast Cheshire County
- Rentals with pools Cheshire County
- Rentals with lake access Cheshire County
- Rentals with a fireplace Cheshire County
- Rentals with a patio Cheshire County
- Rentals with a hot tub 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
- Nashoba Valley Ski Are
- Manchester Country Club - NH
- Bear Brook State Park
- Ekwanok Country Club
- Hooper Golf Course
- The Shattuck Golf Club
- Nashua Country Club
- Veterans Memorial Recreation Area Ski Hill
- Baker Hill Golf Club
- Dorset Field Club
- Clarksburg State Park
- Stump Sprouts Ski Touring Center
- Hildene, The Lincoln Family Home