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Cottages in Middlebury

Cozy cottage with AC and lake access in charming Connecticut suburb.
Terrace/patio

Cozy cottage with AC and lake access in charming Connecticut suburb.

Cozy cottage with AC and lake access in charming Connecticut suburb.
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Exterior

Modern 4 Bedroom Beach House: Ideal for Families & Long Stays

9.4 out of 10, Exceptional, (13)
"We loved our stay in this charming beach home! It was spotlessly clean; located in a quiet neighborhood very near Long Island Sound and great shoreline walks; well provisioned and furnished; and offered easy access to the Yale campus and museums as well as an array of interesting restaurants. Our contact, Tom, was a dream to work with: responsive, considerate and informative. We highly recommend this property for anyone visiting the greater New Haven area. "
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Exterior

Charming, private 2-bedroom cottage on classic New England farm in Washington CT

10.0 out of 10, Exceptional, (6)
"Lovely cottage in a beautiful setting. Well appointed and lots of room to relax, both indoor and outdoor. It was a perfect place to stay while we attended a wedding in the area. "
Charming, private 2-bedroom cottage on classic New England farm in Washington CT
Cozy 2-bedroom Cottage with Access to Bantam Lake
Property grounds

Cozy 2-bedroom Cottage with Access to Bantam Lake

9.6 out of 10, Exceptional, (18)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Fridge, microwave, oven, stovetop

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

10.0 out of 10, Exceptional, (8)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (38)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"Thanks. The little house was lovely."
Historic Whitneyville Cottage
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
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Property grounds

Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC

10.0 out of 10, Exceptional, (7)
"We loved our stay at this stylish and cozy cottage. The views are so pretty and the interior style invites relaxation. "
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
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!
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

9.4 out of 10, Exceptional, (11)
"This is a very cozy attractive cottage and we enjoyed our stay - 3 older women. We did not have a chance to use the lake but we hope we will next year. It was quiet and relaxing."
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
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!
Guest Cottage on Country Estate
Exterior

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (41)
"Cottage was great, very comfy bed, hosts were wonderfuk"
Guest Cottage on Country Estate
Modern Terryville Cottage w/ Deck & Lake View!
Cottage (2 Bedrooms) | 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!
Modern Escape w/ Fire Pit, Near Lake Waramaug
Interior

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) | Front of property

Dainty New Preston Cottage w/ Dock & Lake Views!

3.0 star property
Dainty New Preston Cottage w/ Dock & Lake Views!
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
New Fairfield Vacation Rental w/ Lake Views!
Property grounds

New Fairfield Vacation Rental w/ Lake Views!

3.0 star property
New Fairfield Vacation Rental w/ Lake Views!
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!
Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
Exterior

Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!

10.0 out of 10, Exceptional, (1)
"Lovely little 2/2 house in a great location with just about everything we needed. Very quiet too. Our host, Jonathan was very responsive when we had questions or concerns. We would highly recommend!"
Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
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

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Friendly staff. Nice rooms. Good location/value."
William 1-night trip
Posted 2 days ago
New Haven Hotel

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.