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

Guest favourite
Home in Keene
4.92 out of 5 average rating, 48 reviews

Little House with Lots to Offer

ColleenRating, 5 stars2 weeks ago
I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.
Superhost
Home in Winchendon
4.95 out of 5 average rating, 20 reviews

Amazing Lakefront Home with Pool- Tatum's Place

AnnRating, 5 stars1 month ago
What a perfect places for family and friends long weekend ski trip. Our group consisted of 8 adults and 8 children (ranging ages 4-11). quick drive for tubing and ski/snowboarding. one of the bedrooms was a tricky location since you had to walk through it to get to the lower level kitchen/living room and another bedroom. overall would love to come back again if planning a trip in the area. Ashley was also very easy to communicate with
Top guest favourite
Home in Putney
4.94 out of 5 average rating, 386 reviews

Vermont Botanical Studio Apartment

EmilyRating, 5 stars2 weeks ago
Oliver’s place has everything you need in a perfect peaceful area but close enough to nearby towns like Bellow Falls and Brattleboro where there are many restaurants that Oliver gives recommendations for. The checkin time was also very flexible and Oliver was accommodating to our late arrival.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 208 reviews

The Brick House on Washington Street

KennethRating, 5 stars1 month ago
We had a great stay in Keene. Ruth is a fantastic hostess. Her house is just close enough to Main Street to keep it a walkable distance to multiple restaurants and shopping. The house is a nice cozy spot that was big to accommodate my whole family meeting up for a fun winter weekend in Keene. I would stay there again without hesitation
Top guest favourite
Home in Washington
5 out of 5 average rating, 26 reviews

Winter Fun: Ski, Ice Fish & Relax by Highland Lake

BrianRating, 5 stars1 month ago
Had an excellent stay and Angela was very kind and responded quickly to questions!
Top guest favourite
Home in Walpole
4.99 out of 5 average rating, 73 reviews

Charming, Large House in Walpole NH /VT. Border

SashaRating, 5 stars2 months ago
More than spacious accommodations for our big family! Everything was very comfortable and cozy. The details and aesthetics around the house were emasculate and adorable! 2 minute drive from cute town with adorable grocery store and chocolate/tea place and bigger full size grocery store only 5 minutes away. Kitchen has everything you need to cook!
Top guest favourite
Home in Putney
4.99 out of 5 average rating, 213 reviews

Lovely Brick Schoolhouse

DerekRating, 5 stars3 weeks 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 stars4 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

Top guest favourite
Apartment in Keene
4.99 out of 5 average rating, 132 reviews

Sunny New England Apartment

KatieRating, 5 stars3 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 stars33 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, 158 reviews

Farm land view.

K.ARating, 5 stars1 week ago
I was in Brattleboro for a work training and Peter's place worked very well for me. It is a quiet clean place with basic amenities, close to Brattleboro. Very nice place for reasonable price. Kim
Guest favourite
Apartment in Town of Rockingham
4.95 out of 5 average rating, 268 reviews

Stunning Studio in historic Downtown Bellows Falls

BonnieRating, 5 stars2 weeks ago
We loved our stay at the studio! Remy sent clear instructions( with pictures!) on where to park and how to enter the building. The studio was immaculate and beautifully decorated. Perfect location, steps to coffee shops and restaurants. Looking forward to returning when the weather is a bit warmer!
Guest favourite
Apartment in Keene
4.97 out of 5 average rating, 179 reviews

"Up Top” at Ro & Oak House

KacieRating, 5 stars1 month ago
Awesome spot close to all the food, breweries, & shopping that Keene has to offer. Loved being able to walk everywhere! Hannah was proactive in dealing with the upcoming snow storm and was sure to reach out with directions on where to park & even cleaned up the snow around our cars to make it easier to leave in the morning. Will absolutely be back!
Superhost
Apartment in Town of Rockingham
4.83 out of 5 average rating, 180 reviews

Apartment on Main Street

HeatherRating, 5 stars1 week ago
We stayed a few nights with our pups. I loved the decor choices and overall vibe of this charming older home. Bellow Falls is a super cute town. We appreciated the coffee and snacks provided as well. The bed was a bit too hard for my husband and I but it was doable for a few nights. I left a personal item after I checked out and hosts kindly mailed it back. 5 stars overall :)
Guest favourite
Apartment in Brattleboro
4.89 out of 5 average rating, 557 reviews

Cozy, Private & Great location for exploring VT !

JacquiRating, 5 starstoday
Great place, very clean and convenient for downtown, and a great value, would highly recommend
Superhost
Apartment in Peterborough
5 out of 5 average rating, 3 reviews

"Always Summer" Walk to Downtown

RobertRating, 5 stars6 months ago
The only negative for us was the television/Roku. We were unable to figure out how to watch some live news shows and various other programs that we know were televised. A written primer or directions on how to use Roku effectively would have. been nice. I did not bring this to Lindsay's attention as I should have.

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