Family-friendly holiday rentals in Glastonbury

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a BEAUTIFUL WATERFRONT, 3 bedrooms/3 full bathrooms and a year-round outdoor JACUZZI Also included: gorgeous primary bedroom suite, artistic furnishings, cozy FIREPLACE, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, KAYAKS, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

Bright, clean studio in charming Old Wethersfield

Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This spacious home includes central air, an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large, newly renovated bathroom with spa like jets. His and hers closets. Beautiful fully stocked kitchenette, 2 large screen Smart TVs, 55 inch in living room, 42 inch in bedroom, Free WiFi, dining for 6, all for the comfort and convenience of our guests.

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the live edge bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Classic Farm House on a Working Farm & Vineyard

This quaint farmhouse will be your home away from home. Enjoy the scenery and explore local attractions. The farm house is situated just feet from Joseph Preli Farm and Winery (also owners of the farmhouse) with its bountiful grapevines, fruits and vegetables. The farm and vineyard is known for it's old-world Italian charm. Family owned for 100 years, they respect history by using traditional farming methods and antique tractors. See updates about the farm and winery at @jprelifarm

Charming Cape Home, Close to All

Charming Cape Home in the Heart of Connecticut Enjoy comfort and convenience just 20 mins from Bradley Airport, 10 mins from Hartford, 25 mins from UConn, and 40 mins from New Haven. Nestled on a quiet residential street, our cozy home features multiple beds, fast Wi-Fi, Smart TVs, central air, and a fenced backyard with patio and fire pit. Grocery stores, restaurants, and coffee shops are just 5 minutes away. A perfect retreat for families, professionals, or campus visits!

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

Peaceful Pet-Friendly Retreat Near Hartford and MA

Welcome to your home away from home located steps away from downtown Manchester CT! ✔ Private entrance
✔ 1 comfortable bedroom & full bathroom
✔ Fast Wi-Fi for work and entertainment
✔ In-unit washer & dryer
✔ Complimentary coffee
✔ Pet-friendly accommodations
✔ Backyard access
✔ Quiet, residential setting Conveniently located close enough to major events but in a quaint downtown area making it prefect for short or long term stays.

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

Treehouse - Countryside - Farm Animals - Fire Pit

Escape to the stars in the Private Treehouse nestled among the trees at Bluebird Farm Connecticut. Amenities: ● 100+ Mbps Wi-Fi | Outdoor Fire Pit | Indoor Fireplace ● Interaction w/ Farm Animals | Year-Long Running Water (Sink/Shower) ● Kitchenette | AC in Unit | Free Coffee | Board Games | Books Drive To UCONN (10 Mins) | Hartford (30 Mins) | Boston (1 Hour) | NYC (2.5 Hours)

Flamig Farm Staycation

Very charming private farmhouse tastefully decorated situated in rural West Simsbury CT. Learn every day farm life from helping gather the 200 eggs daily and morning chores of caring for and feeding the petting zoo animals. Please note you are welcome to help the farmer as a family, but please do not leave children unsupervised.