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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
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Dec 12 - Dec 14

Cottages in Middlebury

Our top choices for Middlebury cottages

Charming Connecticut Retreat Near Museums & Hiking
House (3 Bedrooms) | Interior

Charming Connecticut Retreat Near Museums & Hiking

3.0 star property
Charming Connecticut Retreat Near Museums & Hiking
Upscale Waterbury Retreat w/ Indoor Hot Tub!
House (3 Bedrooms) | Interior

Upscale Waterbury Retreat w/ Indoor Hot Tub!

3.0 star property
Upscale Waterbury Retreat w/ Indoor Hot Tub!
Elegant Middlefield Getaway w/ Game Room!
House (4 Bedrooms) | Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
Modern Terryville Cottage w/ Deck & Lake View!
Interior

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
House (3 Bedrooms) | Interior

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

3.0 star property
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Lakefront Home, Close to Mt Southington!
House (3 Bedrooms) | Interior

Lakefront Home, Close to Mt Southington!

3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful house with great views of the lake. "
Lakefront Home, Close to Mt Southington!
Wolcott Home w/ Deck: Near Connecticut Attractions
Interior

Wolcott Home w/ Deck: Near Connecticut Attractions

3.0 star property
Wolcott Home w/ Deck: Near Connecticut Attractions
Modern Escape w/ Fire Pit, Near Lake Waramaug
TV

Modern Escape w/ Fire Pit, Near Lake Waramaug

3.0 star property
Modern Escape w/ Fire Pit, Near Lake Waramaug
Dainty New Preston Cottage w/ Dock & Lake Views!
Cottage (3 Bedrooms) | Interior

Dainty New Preston Cottage w/ Dock & Lake Views!

3.0 star property
Dainty New Preston Cottage w/ Dock & Lake Views!
New Fairfield Vacation Rental w/ Lake Views!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

New Fairfield Vacation Rental w/ Lake Views!

3.0 star property
New Fairfield Vacation Rental w/ Lake Views!
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
House (5 Bedrooms) | Interior

3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven

3.0 star property
3 Mi to Dtwn: Gem w/ Patio & Fire Pit in New Haven
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
House (2 Bedrooms) | Interior

Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

3.0 star property
Watertown Home w/ Yard: 1 Mi to Echo Lake Park!
Hiking Trails On-site: Wooded New Millford Escape!
Cottage (2 Bedrooms) | Interior

Hiking Trails On-site: Wooded New Millford Escape!

3.0 star property
Hiking Trails On-site: Wooded New Millford Escape!
Pet-friendly Connecticut Retreat Near Golfing!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Pet-friendly Connecticut Retreat Near Golfing!

3.0 star property
Pet-friendly Connecticut Retreat Near Golfing!
Spacious Woodbury Home w/ Pool + Hot Tub!
House (4 Bedrooms) | Interior

Spacious Woodbury Home w/ Pool + Hot Tub!

3.0 star property
Spacious Woodbury Home w/ Pool + Hot Tub!
Family-friendly Woodbury Home With Yard + Deck!
House (3 Bedrooms) | Interior

Family-friendly Woodbury Home With Yard + Deck!

3.0 star property
Family-friendly Woodbury Home With Yard + Deck!
Waterfront Retreat w/ Boat Dock & Fire Pit!
Interior

Waterfront Retreat w/ Boat Dock & Fire Pit!

3.0 star property
Waterfront Retreat w/ Boat Dock & Fire Pit!
Group Getaway w/ Outdoor Oasis in Southington!
House (4 Bedrooms) | Interior

Group Getaway w/ Outdoor Oasis in Southington!

3.0 star property
Group Getaway w/ Outdoor Oasis in Southington!
Waterbury Home: Playground & Porch Swing
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Waterbury Home: Playground & Porch Swing

3.0 star property
Waterbury Home: Playground & Porch Swing
Elegant Connecticut Home: Fireplaces, Pet Friendly
House (2 Bedrooms) | Private kitchen | Microwave, dishwasher, cookware/dishes/utensils, paper towels

Elegant Connecticut Home: Fireplaces, Pet Friendly

3.0 star property
Elegant Connecticut Home: Fireplaces, Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlebury Hotel Reviews

Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

10/10 Excellent
"The entire property is well kept. The building is current and great for families. The daily breakfast is a plus! I already booked a return stay!"
Catrina 3-night trip
Posted 14 hours ago
Home2 Suites by Hilton East Haven New Haven

Frequently asked questions

How much do cottages in Middlebury cost?
Prices for cottages in Middlebury range between and per night. Whatever your budget, you'll find a perfect place to reconnect with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Middlebury with Expedia?
Expedia has some superb cottages in Middlebury, so start packing for an unforgettable stay on nature's doorstep. If you're sticking to a budget, choose how much you'd like to spend and the star rating of your property. Or, make the most of our filters to search for cottages with free WiFi or a pool. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Middlebury?
Expedia can help you easily track down cheap cottages in Middlebury. To lock in your special stay in just a few keystrokes, simply use our handy filter tool to tailor your search results by star rating, amenities and budget.