Family-friendly holiday rentals in Middletown

Top Guest favourite

Guest favourite

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.

Indoor spaces · Kitchen · Location

Top Guest favourite

Guest favourite

Family Stays, CT

Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

Kitchen · Indoor spaces · Sleep quality

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Guest favourite

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Family · Kitchen · Sleep quality

Updated 2-bedroom Near Wesleyan-Middletown

Welcome to Middletown! We are sure you will love your stay in this newly renovated apartment. This centrally located 2- bedroom apartment sleeps 4 comfortably with a large king bed in one bedroom with a TV and full bed in another. This apartment is on the second floor. Full kitchen with laundry in unit. Walk in shower in bathroom. Off street parking available. Walking distance to shops and restaurants on Main Street, Wesleyan University (1-mile walk) and Middlesex Hospital. Easy access to Rt 9

Family · Indoor spaces · Decor

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Guest favourite

Anchors' Away-

Escape to a charming lakefront retreat where peaceful mornings, panoramic water views, are the gift that nature gives you. conveniently located near major highways, shopping, restaurants and local attractions, - Our cottage offers the best of two worlds-tranquil relaxation and easy access to everything you need. Guests will be given a Hold Harmless Agreement to sign upon reservation acceptance-There are kayaks available to use- A waiver has to be signed before they can be used on the lake

Indoor spaces · Family · Getting around

Bright & Private WHOLE HOUSE 4 YOU Near Everything

Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

Kitchen · Indoor spaces · Accuracy

Beautiful Lake House on Lake Pocotopaug

Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

Family · Indoor spaces · Amenities

Top Guest favourite

Guest favourite

Guest Suite, 2nd floor, 3 bedrooms, near Downtown!

Close to Downtown Middletown & Wesleyan University, located between Hartford & New Haven. Private floor with 3 bedrooms - two bedrooms have queen beds, third bedroom also serves as a living room with a sleeper sofa, listing sleeps 6 total. Large bathroom with double sinks & shower (no tub). NO KITCHEN but there is a mini-fridge, microwave & Keurig, with coffee, tea, water & supplies provided. Perfect for Wesleyan parents, students & visitors, couples, families, wedding & business travelers.

Kitchen · Family · Outdoor spaces

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kitchen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

Kitchen · Family · Getting around

Relax by the water in a 4 bedroom house

Relax with the whole family at this recently renovated, spacious 4 bedroom house on Beaver Pond. Centrally located in the crossroads of Connecticut and a short train ride away from NYC, come relax by the water in a quiet neighborhood setting. Stay home and enjoy a kayak or canoe on the pond or visit the many nearby attractions like mini golf, skiing, hiking or the rest that Connecticut has to offer. The home has been recently remodeled and has a very spacious yard.

Family · Indoor spaces · Backyard

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.

Family · Kitchen · Access

Direct Waterfront Cottage on Moodus Reservoir.

Relax with the whole family at this peaceful place to stay with direct access to the lower Moodus Reservoir. The backyard leads out to the lake with a small beach area (fits approximately two lawn chairs). Sit on the patio by the fire pit and enjoy the view or grab a kayak, pedal boat, or paddleboard and enjoy your time directly on the lake.

Kitchen · Family · Accuracy