Search vacation rentals in Middlebury, CT from 100+ sites!

This Woodbury cottage is conveniently located near Flanders Nature Center and Steep Rock Preserve, with Hollister House Garden, Glebe House Museum, and Bellamy-Ferriday House and Garden also within easy reach.
This family-friendly retreat offers 1000 square feet of living space, accommodating up to 6 guests with 3 bedrooms and 1 bathroom, and features include WiFi, air conditioning, and a microwave oven.

This Waterbury, Connecticut cabin offers a spacious 2190-square-foot retreat near Brass Mill Center and Bristol Commons shopping centers, with easy access to Whittemore Glen and Black Rock State Parks.
The three-bedroom home sleeps five, features two bathrooms, a fully equipped kitchen with a fridge and dishwasher, and includes amenities such as Wi-Fi, air conditioning, and a washer/dryer.

This Roxbury apartment is located just a short drive from Lake Waramug and a few miles from the town center of Woodbury, offering easy access to local attractions and amenities. The apartment consistently receives excellent ratings for user experience, location, and cleanliness.
This spacious 5-bedroom home spans 3800 square feet and comfortably accommodates up to 12 guests. The apartment offers a range of amenities, including a heated pool, Jacuzzi, sauna, game room, movie room, and a fully stocked kitchen with a grill and smoker for outdoor cooking.

This spacious apartment is located in Southbury, just a short drive from the town center and close to the scenic trails of the Pomperaug River, offering a peaceful retreat while still being conveniently close to attractions. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This 3-bedroom, 2-bathroom home comfortably accommodates up to 8 guests, making it ideal for families or groups of friends. Amenities include a well-equipped kitchen, a large yard with a swing and fire pit, a washer and dryer, and parking for multiple vehicles.

Serenity Cottage, a one-bedroom house located in Woodbury, Connecticut, offers a peaceful farm stay near Woodbury's antique shops on the Antique Trail of New England and farm-to-table restaurants.
This 1-bedroom rental features a pull-out couch, accommodating up to four guests, and includes a fully equipped kitchen, washer/dryer, and dedicated parking; guests can enjoy the private backyard and explore the horse rescue farm (excluding barns).

This pet-friendly vacation home is located in Waterbury, Connecticut, just a short drive from popular attractions like Flanders Nature Center, Abbey of Regina Laudis, and Lake Compounce. The house is ideal for families or groups visiting Waterbury, with its convenient location near major attractions and universities.
The 3-bedroom, 2-bathroom house comfortably accommodates up to 10 guests. The fully equipped kitchen includes a fridge, microwave, oven, and dishwasher, making it easy to prepare meals during your stay. Other amenities include a fitness center, parking, and free Wi-Fi.

This Terryville residence offers proximity to Rockwell Park and the Witch's Dungeon Classic Movie Museum, both a 5-minute drive away.
This dwelling accommodates up to 10 guests with 3 bathrooms, a full kitchen featuring a dishwasher, and in-unit laundry, plus complimentary Wi-Fi and on-site parking.

This charming cottage is located in Terryville, just a short drive from Cedar Lake and Rockwell Park, offering easy access to outdoor activities and a peaceful setting. The cottage has earned a "very good" user rating, making it a popular choice for travelers.
The cottage offers 800 square feet of living space, comfortably accommodating up to four guests. It features a fully equipped kitchen, air conditioning, a fireplace, a private garden, and parking, making it an ideal choice for a relaxing getaway.

This 1190 sq ft apartment in Waterbury is located near universities, hospitals, parks, and local events, with the Mattatuck Museum Arts and History Center and Palace Theatre just a short distance away. This rental offers two queen beds, a bathroom with a bathtub and hair dryer, and a sofa bed, accommodating up to six guests, and is conveniently located near Quassy Amusement Park and outdoor recreational activities.

This recently renovated 1-bedroom suite in Waterbury is located 12 miles from Flanders Nature Center and the Witch's Dungeon Classic Movie Museum.
This 170 square foot executive suite offers air conditioning, a full kitchen, complimentary WiFi, and parking for up to 5 guests, with a terrace for your enjoyment.

This antique colonial farmhouse in Woodbury is situated on over three private acres, offering a secluded New England retreat just minutes from the center of town and attractions like the Glebe House Museum and Quassy Amusement Park. This 4-bedroom, 2-bathroom house accommodates up to 8 guests and features two fireplaces, a renovated kitchen, outdoor living space with a griddle and fire pit, and is pet-friendly with internet and air conditioning.

This 2-bedroom house offers a peaceful escape in a Waterbury residential district, featuring front access and a private yard with a patio.
This pet-friendly apartment accommodates up to 4 guests, providing amenities like air conditioning, a full kitchen with a dishwasher, and access to an on-site fitness center.

This Southbury apartment rental is conveniently located near Flanders Nature Center (12 miles) and the Abbey of Regina Laudis (13 miles), offering easy access to outdoor recreation and cultural attractions.
The 850-square-foot unit features one bedroom, one bathroom, and sleeps three, complete with a fully equipped kitchen (including a dishwasher), in-unit laundry, free Wi-Fi, and private parking.

This waterfront apartment in Southbury, Connecticut, is situated within walking distance of Southford Falls State Park and a short drive from Danbury, Litchfield, Hartford, and New Haven. It has an excellent user rating.
The apartment features a private entrance and emergency exit, over 1000 square feet of living space, one bedroom, one bathroom, and a guest capacity of two. It includes a fully-equipped kitchen with a fridge, microwave oven, and dishwasher. The apartment is pet-friendly for a fee and offers convenient access to restaurants and amenities within walking distance.

This private historic home in Watertown is within walking distance of the city's main attractions, including the Arsenal Street District, the Charles River Esplanade, and the Watertown Free Public Library. It has excellent user, location, and cleanliness ratings.
The spacious house has 5 bedrooms, 3 bathrooms, and a guest capacity of 10. It offers a unique glimpse into Watertown's rich past, with two cozy fireplaces, an inviting porch, and a spacious backyard with a fire pit. It also has a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, internet, and parking.