Winchester Family Rentals & Large Homes

Find Family-Friendly Vacation Rentals Near Winchester

About Winchester Family Rental on Rent By Owner

We have 132 family-friendly rentals in Winchester. Looking for the best place to stay in Winchester for your family reunion or retreat?

Rent By Owner 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, 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 Winchester with you. RBO 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 Winchester family vacation rental on Rent By Owner gives you many options to aid you in making the perfect selection for your family holiday. Our Winchester 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.

Rent By Owner offers thousands of rentals.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.

Show more
Show less

Frequently Asked Questions About Winchester Family Rentals

There are a lot of options in Winchester. If you plan on staying in the Winchester area, consider making a reservation for a few nights at one of these properties as these have been rated the top Family Rentals in Winchester:

The average price per night for a family holiday rental in Winchester is $346. Check the list of kid-friendly accommodations in Winchester.
There are 132 2-bedroom rental properties that are available in Winchester. You can book for your next trip with Rent By Owner.
Yes, here are some top-rated family vacation rentals in Winchester that have a private swimming pool:

Check all holiday rentals with a pool in Winchester on Rent By Owner.

Yes, We have 132 direct by owner rentals in Winchester.