Family-friendly holiday rentals in Windham County

4.91 out of 5 average rating, 144 reviews

Guest suite in Granby

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

4.89 out of 5 average rating, 400 reviews

Villa in Norwich

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

4.99 out of 5 average rating, 114 reviews

Home in Groton

Unique Retreat w/Private Patio, 4 King Beds & BBQ

Welcome to your next charming and unique retreat offering an ideal blend of style and comfort. The spacious interior seamlessly connects the living room, kitchen, and dining areas, with elegant stained glass windows adding a touch of character. Cozy bedrooms all feature king-sized beds for peaceful slumber. Outside, the private patio deck invites you to relax on sun loungers, indulge in outdoor dining with the BBQ, and create memories with family and friends. ✔ Private Patio ✔ BBQ ✔ King Beds

4.99 out of 5 average rating, 141 reviews

Home in Groton

Mystic Blue Belle - a Vacation Paradise

If you love Victorian elegance, beaches, family fun, restaurants and a village of inviting shops, you have found it. Look no more! Filled with old world charm, this majestic 1880 Victorian home sleeps 10 in 4 private bedrooms with 2.5 baths. Voted, “#1 World’s vacation destination.” Escape & unwind in a classic masterpiece of yesteryear fully updated with all the modern conveniences. The site could easily be used for reunions, gatherings or even a quaint wedding venue, graduations and more!

4.96 out of 5 average rating, 188 reviews

Romantic Seaside Cottage in Mystic

This cozy seaside cottage with sleep loft has the look and feel of an old classic yacht inside with modern amenities. Couples will love the water views, screened porch, gas-wood stove, heated stone floor in cedar bathroom, outdoor shower and patio. Another larger 2 bedroom cottage on property is for rent also for families with younger children. This rental is NOT suitable for toddlers or children under 12 due to the open balconies, railings and narrow spiral staircase to the loft.

4.97 out of 5 average rating, 219 reviews

Perfect New England Getaway has a pool/ hot tub

traditional New England style that is not just a great home, but a great vacation compound with lots of amenities and outdoor living spaces. Enjoy recreational activities on land and sea that abound locally. Mystic, Stonington Borough, Westerly, and Watch Hill are all close IMPORTANT INFORMATION: Please be advised Stonington, CT has a STRICT OUTSIDE Noise ordinance after 10pm that is enforced by the Police. If a report is generated for any reason , you will forfeit your deposit.

4.97 out of 5 average rating, 188 reviews

Relax or roam from our private spacious home

Bright and sunny newly renovated second and third floor of house built in late 1800s. Three blocks from Mystic Seaport, a short walk to downtown Mystic. Off street parking on the side of the house. House has plenty of space with two bedrooms plus a bonus room with a queen size futon. I Homey and comfortable to make you feel you can put your feet up and relax. User friendly. First floor is used as an office only on weekdays. Only 1/2 mile from Mystic Amtrak station, an easy walk.

Superhost

4.87 out of 5 average rating, 113 reviews

Waterfront Cottage with Dock

Arts and Crafts cottage on an ocean cove in Stonington with dock and close to the beaches. On same cove as Saltwater Farm Vineyard and nearby to Mystic Aquarium and Seaport, great restaurants, and Foxwoods and Mohegan Sun resorts. You’ll love the backyard and dock. I offer complimentary canoe, kayak and paddle board use so you can enjoy the water. Bring your own boat or rent one for 50% off at Stonington Marina. My place is good for couples, families with kids, and pets.

4.98 out of 5 average rating, 171 reviews

Historic charm & modern luxury in downtown Mystic

We are long-time AirBNB guests who have tried to create the home we are always looking to book -- family friendly with modern amenities. Open floor plan on the main level, new heat and air con throughout the house, three bedrooms and family bathroom on the second floor. Art supplies, toys and children's books all ready for you as well as a pack n play and booster seat. Backyard oasis with pergola, walking distance to drawbridge. Pets considered on a case by case basis.

Superhost

Home in Groton

4.89 out of 5 average rating, 194 reviews

Cozy Shoreline Cottage, Sleeps 6

Riverscape Cottage is a short drive to beautiful Mystic, the casinos, the Coast Guard Academy, Conn College, restaurants and dining, the beach, nightlife, and family-friendly activities. You’ll love my place because it is adjacent to a quiet town park and is a short walk to Bluff Point State Park which offers excellent hiking and biking. Launch the 2 kayaks or the canoe right from the property!

4.98 out of 5 average rating, 183 reviews

Home in mystic

Charming Downtown Mystic Historic House

Enjoy Mystic in historic John Denison house. We are close to all Mystic has to offer. Great views, location, and impeccable cleanliness. Perfect for couples, solo adventurers, business travelers, and families. Guests required age 25 or older verified by Gov ID to book. Declared pet fee $150. Undeclared pets incur an automatic $500 charge. Please note: narrow stairs to the 2nd floor.