Kid-friendly vacation rentals in Cheshire County

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Cheshire County kid-friendly rentals

Kid-friendly house rentals

Superhost
Home in Rindge
5 out of 5 average rating, 3 reviews

Secluded lakefront vacation home

ClaudiaRating, 5 stars2 months ago
Beautiful home. Well kept. Hosts super accessible and very friendly. We felt like home and house is super cozy
Guest favourite
Home in Keene
4.92 out of 5 average rating, 50 reviews

Little 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 Winchendon
4.95 out of 5 average rating, 22 reviews

Amazing Lakefront Home with Pool- Tatum's Place

NidhiRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Keene
4.93 out of 5 average rating, 209 reviews

The Brick House on Washington Street

MariRating, 5 stars1 week ago
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!
Top guest favourite
Home in Washington
5 out of 5 average rating, 28 reviews

Spring Getaway: Kayak & Unwind by Highland Lake

Nicole ERating, 5 stars1 month ago
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!"
Top guest favourite
Home in Walpole
4.99 out of 5 average rating, 74 reviews

Charming, 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 Putney
4.99 out of 5 average rating, 214 reviews

Lovely Brick Schoolhouse

DerekRating, 5 stars2 months ago
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!
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars6 months ago
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

Guest favourite
Apartment in Winchester
4.91 out of 5 average rating, 198 reviews

Downtown Loft next to Distillery

NicholasRating, 5 stars1 month ago
What a great stay! We would definitely return. Everything was perfect.
Top guest favourite
Apartment in Keene
4.99 out of 5 average rating, 132 reviews

Sunny New England Apartment

KatieRating, 5 stars5 months ago
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.
Superhost
Apartment in Jaffrey
4.94 out of 5 average rating, 48 reviews

Spacious First Floor of Historic House

NeilRating, 5 stars34 months ago
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.
Top guest favourite
Apartment in Vernon
4.96 out of 5 average rating, 160 reviews

Farm land view.

LorrieRating, 5 stars1 month ago
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.
Guest favourite
Apartment in Town of Rockingham
4.95 out of 5 average rating, 271 reviews

Stunning Studio in historic Downtown Bellows Falls

KcRating, 5 stars1 month ago
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.
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 183 reviews

Apartment on Main Street

meganRating, 5 stars1 week ago
Perfect stay for our short trip! Whitney is wonderful and so responsive!
Guest favourite
Apartment in Brattleboro
4.89 out of 5 average rating, 563 reviews

Cozy, Private & Great location for exploring VT !

ArthurRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment in Peterborough
4.92 out of 5 average rating, 189 reviews

Private Apartment with a Mt. view

BradRating, 5 stars3 months ago
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.

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