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

20 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Middlebury, CT vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Middlebury, CT

Discover Central Vacation Rentals in Middlebury, CT

From vibrant downtown areas to historic streets, these Middlebury, CT vacation rentals put you close to everything worth seeing.

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy - Middlebury, CT
10 4 reviews

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy

house, Bethlehem
This Bethlehem vacation home, near the Abbey of Regina Laudis (2.1 miles) and Flanders Nature Center (2.9 miles), offers a tranquil woodland retreat.
The 1840-square-foot property features one bedroom, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, spa, outdoor fireplace, and free Wi-Fi.
Historic Litchfield County Home - Middlebury, CT
9.8 32 reviews

Historic Litchfield County Home

apartment, Watertown
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.
6-acre Luxurious Country Home W Goddess Pt Lookout - Middlebury, CT
10 20 reviews

6-acre Luxurious Country Home W Goddess Pt Lookout

apartment, Woodbury
This Woodbury vacation home sits on the shores of Lake Quassapaug, just a short drive from attractions like Quassy Amusement Park and the Glebe House Museum. Guests consistently rate the home excellent for its location, cleanliness, and overall experience.
The 4-bedroom home comfortably accommodates up to 8 guests, offering plenty of space for families or groups of friends. Enjoy lakefront views, a spacious patio, a cozy fireplace, and a fully equipped kitchen, along with amenities like a tennis court and a spa.
Cozy Nature Retreat At Chateau Madeux - Middlebury, CT
9.8 67 reviews

Cozy Nature Retreat At Chateau Madeux

apartment, Southbury
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.

Best Middlebury, CT vacation rentals with air conditioning

Idyllic Country House With Pool - Middlebury, CT
9.0 2 reviews

Idyllic Country House With Pool

apartment, Bethlehem
This Bethlehem vacation home sits on 35 acres, a 3-minute drive from Bethlehem and 12 minutes from Litchfield, Connecticut, offering complete privacy in a tranquil country setting with magnificent mountain views.
The 4-bedroom, 4-bathroom house comfortably sleeps eight guests and boasts a fully equipped kitchen with high-end appliances (Wolf range, double oven), a heated pool (seasonal), an indoor infrared sauna, and extensive outdoor space including a courtyard with a BBQ area.
New! Charming Lakefront House - Middlebury, CT
9.8 34 reviews

New! Charming Lakefront House

apartment, Plymouth
This lake house is situated on Fall Mountain Lake, a private, freshwater community lake, just 20 minutes from Mount Southington. The property has excellent user, location, and cleanliness ratings.
The vacation rental has 3 bedrooms, 1 bathroom, and comfortably sleeps 6 guests. Enjoy amenities like a private dock, a fireplace, a modern kitchen, a spacious deck with lake views, and a variety of water activities including kayaking, paddle boarding, and fishing.
Luxurious Lakefront Retreat (Sleeps 11) - Middlebury, CT
10 2 reviews

Luxurious Lakefront Retreat (Sleeps 11)

apartment, Southbury
This lakefront residence in Southbury offers direct water access and stunning views, providing a tranquil escape close to the area's natural beauty.
This spacious 4-bedroom, 4-bathroom condo accommodates up to 11 guests, featuring a fully equipped chef's kitchen, an entertainment lounge with a pool table, a heated garage game suite, and a lakeside lanai, with pets allowed and internet provided.
Historic Litchfield County Home - Middlebury, CT
No reviews

Historic Litchfield County Home

house, Watertown
This historic Litchfield County home in Watertown offers 1 bedroom and 1 bathroom, accommodating up to 3 guests with air conditioning and parking.
This property is located 5.4 miles from Flanders Nature Center and 6.5 miles from the Abbey of Regina Laudis, with proximity to the Witch's Dungeon Classic Movie Museum at 13 miles and Lake Compounce at 17 miles.

Frequently Asked Questions about vacation rentals in Middlebury, CT

  • What other towns or cities can be easily accessed from Middlebury, CT?

    Middlebury is conveniently located near a number of other towns and cities. Waterbury is just a short drive away, and you can easily get to New Haven, Hartford, and New York City from there. If you're looking for a more scenic drive, try heading to Litchfield, which is known for its beautiful countryside and historic homes.
  • What are the best Airbnb and vacation rentals in Middlebury, CT?

    Private One Bedroom Apartment In Middlebury - Ct and Lake Quassapaug Homestead are among the best Airbnb and vacation rentals in Middlebury, CT.

  • What amenities are commonly available in vacation rentals in Middlebury, CT?

    Vacation rentals in Middlebury typically offer a range of amenities, depending on the size and type of property. You can expect to find things like kitchenettes, laundry facilities, Wi-Fi, and parking. Some rentals may also offer fireplaces, hot tubs, or outdoor space.
  • What are the most popular Airbnbs in Middlebury, CT?

    Among the Airbnbs in Middlebury, CT, Private One Bedroom Apartment In Middlebury - Ct and Lake Quassapaug Homestead are the most popular ones.

Popular destinations

Find the Best Vacation Rentals with Balconies in Middlebury, CT

Enjoy stunning views from your private terrace when you book one of these vacation rentals in Middlebury, CT.

Historic Litchfield County Home - Middlebury, CT
No reviews

Historic Litchfield County Home

house, Watertown
This historic Litchfield County home in Watertown offers 1 bedroom and 1 bathroom, accommodating up to 3 guests with air conditioning and parking.
This property is located 5.4 miles from Flanders Nature Center and 6.5 miles from the Abbey of Regina Laudis, with proximity to the Witch's Dungeon Classic Movie Museum at 13 miles and Lake Compounce at 17 miles.
Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy - Middlebury, CT
10 4 reviews

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy

house, Bethlehem
This Bethlehem vacation home, near the Abbey of Regina Laudis (2.1 miles) and Flanders Nature Center (2.9 miles), offers a tranquil woodland retreat.
The 1840-square-foot property features one bedroom, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, spa, outdoor fireplace, and free Wi-Fi.
Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust - Middlebury, CT
9.6 20 reviews

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust

apartment, Watertown
This family-friendly vacation home is located just outside Watertown, within a 10 km radius of Black Rock State Park, Bellamy-Ferriday House and Garden, and The Christmas Shop. It's perfect for families looking for a peaceful retreat close to attractions. The house has received excellent ratings from previous guests.
This 4-bedroom, 4-bathroom vacation rental comfortably sleeps 12 guests in its 5,400 square feet of space. Enjoy a range of amenities like a private pool, fitness center, sauna, and spa, as well as a tennis court, garden, and game room for entertainment.
Litchfield County Four Season Country Paradise - Middlebury, CT
9.5 119 reviews

Litchfield County Four Season Country Paradise

apartment, Roxbury
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.

Neighborhoods and points of interest in Middlebury, CT

Our Favorite Family-Friendly Vacation Rentals in Middlebury, CT

Ideal for family vacations, these Middlebury, CT rentals or Airbnbs offer spacious layouts near top city attractions.

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy - Middlebury, CT
10 4 reviews

Nature's Nest - Woodland Retreat - Fireplace - Quiet And Cozy

house, Bethlehem
This Bethlehem vacation home, near the Abbey of Regina Laudis (2.1 miles) and Flanders Nature Center (2.9 miles), offers a tranquil woodland retreat.
The 1840-square-foot property features one bedroom, two bathrooms, sleeps thirteen guests, and includes a fully equipped kitchen, spa, outdoor fireplace, and free Wi-Fi.
Cozy Nature Retreat At Chateau Madeux - Middlebury, CT
9.8 67 reviews

Cozy Nature Retreat At Chateau Madeux

apartment, Southbury
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.
Zoom In Map To 5* Roxbury Washington - Best Towns! - Middlebury, CT
10 7 reviews

Zoom In Map To 5* Roxbury Washington - Best Towns!

apartment, Roxbury
This beautifully preserved 1890s Victorian home, located in Roxbury's renowned neighborhood, offers easy access to local attractions and is less than two hours from New York City.
This 2,050-square-foot house boasts three bedrooms, sleeps eight guests, and includes a swimming pool, Jacuzzi, spa, tennis court, and a two-car garage, plus modern amenities like WiFi and central air conditioning.
Historic Litchfield County Home - Middlebury, CT
9.8 32 reviews

Historic Litchfield County Home

apartment, Watertown
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.

Best Middlebury, CT vacation rentals with parking

Bacon Pond Manor - Middlebury, CT
No reviews

Bacon Pond Manor

gîte, Woodbury

Popular Luxury Vacation Rentals in Middlebury, CT

Discover high-end comfort in Middlebury, CT with upscale rentals that prioritize luxury and guest satisfaction.

Cozy Nature Retreat At Chateau Madeux - Middlebury, CT
9.8 67 reviews

Cozy Nature Retreat At Chateau Madeux

apartment, Southbury

Top Dog-Friendly Vacation Rentals in Middlebury, CT

Traveling with pets? These dog-friendly vacation rentals and Airbnbs in Middlebury, CT are steps away from dog parks and city walks.

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust - Middlebury, CT
9.6 20 reviews

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust

apartment, Watertown
6-acre Luxurious Country Home W Goddess Pt Lookout - Middlebury, CT
10 20 reviews

6-acre Luxurious Country Home W Goddess Pt Lookout

apartment, Woodbury
Luxurious Lakefront Retreat (Sleeps 11) - Middlebury, CT
10 2 reviews

Luxurious Lakefront Retreat (Sleeps 11)

apartment, Southbury
Luxurious Lakefront Retreat   Sleeps 11 - Middlebury, CT
No reviews

Luxurious Lakefront Retreat Sleeps 11

apartment, Newtown

Top-Rated Vacation Rentals with a Pool in Middlebury, CT

A Middlebury, CT vacation rental with a pool ensures a refreshing swim in the heart of the city is always an option.

Zoom In Map To 5* Roxbury Washington - Best Towns! - Middlebury, CT
10 7 reviews

Zoom In Map To 5* Roxbury Washington - Best Towns!

apartment, Roxbury
Idyllic Country House With Pool - Middlebury, CT
9.0 2 reviews

Idyllic Country House With Pool

apartment, Bethlehem
Litchfield County Four Season Country Paradise - Middlebury, CT
9.5 119 reviews

Litchfield County Four Season Country Paradise

apartment, Roxbury
Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust - Middlebury, CT
9.6 20 reviews

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust

apartment, Watertown

Check Out Vacation Rentals with a Hot Tub in Middlebury, CT

These Middlebury, CT city rentals feature private hot tubs, providing the perfect sanctuary after a day of urban exploration.

Zoom In Map To 5* Roxbury Washington - Best Towns! - Middlebury, CT
10 7 reviews

Zoom In Map To 5* Roxbury Washington - Best Towns!

apartment, Roxbury
Litchfield County Four Season Country Paradise - Middlebury, CT
9.5 119 reviews

Litchfield County Four Season Country Paradise

apartment, Roxbury
Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust - Middlebury, CT
9.6 20 reviews

Swiss Chalet Amidst Sixteen Acres In Litchfield Hills Surrounded By Land Trust

apartment, Watertown
©2026 cozycozy.com