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Cheshire Family Rentals & Large Homes
Find Family-Friendly Vacation Rentals Near Cheshire
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About Cheshire Family Rental on PetFriendly
We have 57 family-friendly rentals in Cheshire. Bring your family dog and include the whole family. Looking for the best place to stay in Cheshire for your family reunion or retreat?
PetFriendly offers a variety of options of homes with multiple bedrooms and beds - perfect for large families or groups, and inter-generational travel. Find a place that is good for all ages (and pets), even if you have a large family with kids, parents, cousins, aunts, uncles, in-laws, grandma and grandpa, and even the family pet that'll be coming to Cheshire with you. PetFriendly family rentals have rental properties that would accommodate everyone, saving money vs. a hotel, and giving everyone enough space for relaxation. Smaller or single families are not left out, there’s something special for everyone.
Renting a Cheshire family vacation rental on PetFriendly gives you many options to help you in making the perfect selection for your family holiday. Our Cheshire house rentals come with all the required amenities you need for planning the perfect family vacation; such as comfortable beds, TVs, spas, bathtubs, balconies, lawns, playrooms, cribs, Wi-Fi, or swimming pools for an unforgettable trip with the entire family and kids.
PetFriendly offers thousands of rentals and has mapped out all of our properties against the nearest dog park. There are many well-equipped cabins, villas, family condos, lodges, and more to accommodate large groups or multiple families. Many of our holiday rentals also have large private pools and allow you to extend your budget.
Frequently Asked Questions About Cheshire Family Rentals
There are a lot of options in Cheshire. If you plan on staying in the Cheshire area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Cheshire:
- Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Berkshire Mountain Escape: family retreat open now for fall color and skiing!
- Brooksong, the perfect Berkshires getaway
- Berkshires Lakefront Retreat by Evergreen Home
- Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
- Chic Berkshire Retreat by Evergreen Home
- Mountain Blossom Retreat by Evergreen Home
- Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
- Mountain getaway in the Berkshires - walk to trails & town!
- 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
- Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Mountain getaway in the Berkshires - walk to trails & town!
- Harbour House Inn
- Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Check all holiday rentals with a pool in Cheshire on PetFriendly.