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Cottages in Middlebury

Cozy Cabin @ Sticks & Stones Farm
Interior

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very Good, (7)
"Nice clean cabin. Good communication with host."
Cozy Cabin @ Sticks & Stones Farm
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (34)
"Clean stunning views amazing host "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Dainty New Preston Cottage w/ Dock & Lake Views!
Outdoor dining

Dainty New Preston Cottage w/ Dock & Lake Views!

9.0 out of 10, Wonderful, (35)
"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"
Dainty New Preston Cottage w/ Dock & Lake Views!
Historic Whitneyville Cottage
Fridge, microwave, oven, stovetop

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."
Historic Whitneyville Cottage
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
Property grounds

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (91)
"Place was big enough for the two of us and a dog. Was very thankful the tiny home was dog friendly. Clean- location was good.Driveway was scary- to pull in and out. "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!
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, (17)
"Even with horrible weather, we had a wonderful stay!"
Cozy 2-bedroom Cottage with Access to Bantam Lake
Guest Cottage on Country Estate
Outdoor dining

Guest Cottage on Country Estate

9.2 out of 10, Wonderful, (41)
"the location and size of cottage were just what we were looking for."
Guest Cottage on Country Estate
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

9.6 out of 10, Exceptional, (14)
"Situated right on the lake. Easy to get to, nice working fireplace, lots of fun stuff for the kids and comfortable furniture. We really enjoyed our stay."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
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, (10)
"The owners freshly love this place"
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
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
Streamside Cottage @ Sticks & Stones Farm
Fridge, microwave, oven, coffee/tea maker

Streamside Cottage @ Sticks & Stones Farm

10.0 out of 10, Exceptional, (1)
"This is a great property (stream nearby, outdoor seating, few neighbors). The house is adequately spacious, whimsical, and unique with a rustic barn feel. Our family of 5 slept well and felt relaxed during our summer visit. It was nice to have a full kitchen, all that natural light and it was quiet.The light switches were a bit hard to find at times. The fire bricks in front of the wood stove were also something you had to pay attention to or you might stub a toe. Finally, there is a lack...
Streamside Cottage @ Sticks & Stones Farm
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!
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Beach nearby, beach towels

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

9.8 out of 10, Exceptional, (11)
"Easy in and out and fast communication for any questions"
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
Modern Terryville Cottage w/ Deck & Lake View!
Dining

Modern Terryville Cottage w/ Deck & Lake View!

9.2 out of 10, Wonderful, (5)
"This cottage was just as the pics show. Great communication with host prior to visit as well as a "Thank you" This is the perfect spot to relax & recharge from stress. The cottage wraps you in warmth, and charm."
Modern Terryville Cottage w/ Deck & Lake View!
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, (3)
"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 Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Terrace/patio

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

10.0 out of 10, Exceptional, (7)
"Loved staying at this spot when dropping our daughter off for school!"
Cozy Lakefront Cottage on Candlewood- swim, relax, hike, wineries 90min from NYC
Cozy Country Cottage
TV, fireplace

Cozy Country Cottage

2.0 star property
9.0 out of 10, Wonderful, (6)
"Very accommodating and understanding host.They are warm and willing to listen and make your stay as comfortable as possible. Trent and his family will go out of their way to make the stay memorable.. I would highly recommend the stay at this accommodation to everyone. A home away from home."
Cozy Country Cottage
Elegant Middlefield Getaway w/ Game Room!
Interior

Elegant Middlefield Getaway w/ Game Room!

3.0 star property
Elegant Middlefield Getaway w/ Game Room!
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!
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!
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

Wyndham Southbury

Wyndham Southbury

10/10 Excellent
"This is a beautiful hotel nestled in the middle of forested hills of the interstate. The lobby is grand, and the rooms are large and comfortable. The 50" flat-screen tv is nice with lots of channels. The beds are very comfortable and the linens clean and bright white.the bathrooms are updated and bright, and the shower performed like a champ. I enjoyed the large swimming pool, especially at 6:00 am. A great syay, staff are friendly and helpful "
Howard 2-night trip
Posted 2 days ago
Wyndham Southbury

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.