Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 331 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Top guest favorite

Guest suite in Watertown

5 out of 5 average rating, 74 reviews

Private King suite w/ separate entry-Walk to Taft!

Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.

Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 199 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Top guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 309 reviews

Quiet cottage w/chickens, gardens near Litchfield

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and summer fun!

Guest favorite

Guesthouse in Watertown

4.92 out of 5 average rating, 48 reviews

Private studio guesthouse

Kick back and relax in this peaceful, quiet, stylish space with high ceilings, central heat and air, huge bathroom, mini kitchen, fridge, microwave, coffee maker, 75" TV, onsite laundry and workout equipment when needed, private parking space, private entrance, high-speed internet, countless local restaurants, fast food chains and cafes, all major supermarkets, hospitals and doctors offices, post offices, easy access to numerous lakes, golf course and wineries. Indeed, a home away from home.

Top guest favorite

Home in Middlebury

5 out of 5 average rating, 12 reviews

New England Charm!

Kick back and relax in this calm, stylish space located on a country dead end road. Work from home with high speed WiFi, monitor, and light blocking shades. Close to Taft and Westover. Directly on the Bike Trail. E-bikes available. Close to Vyne. This house is 500 square feet with 1 bedroom, 1 bathroom, and a combination living room, kitchen and office space. Perfect for one person or a couple. There is also a small loft on the 2nd floor. Enjoy the large back deck and fire pit. T

Top guest favorite

Home in Waterbury

4.94 out of 5 average rating, 81 reviews

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

Top guest favorite

Home in Southbury

4.98 out of 5 average rating, 125 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working (in progress) farm bordered by 155 acres of protected land trust with marked hiking trails. Southford Falls and Kettletown State Park are within minutes for fishing, picnicking, and hiking. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two.

Guest favorite

Home in Woodbury

4.94 out of 5 average rating, 99 reviews

Ferris House: Private 19th Century Home

Private 19th century home situated in a beautiful garden setting. Gourmet kitchen. Well appointed rooms. New England charm at its best. Enjoy nearby top restaurants and antique shops. We are also very close to private schools in the area such as Taft and Westover, which makes this an excellent location for visiting family and friends. We welcome couples, solo adventurers, business travelers and families (with kids).

Guest favorite

Apartment in Southbury

4.86 out of 5 average rating, 111 reviews

Suite Hill Studio

A private entrance to your studio located at the top of a hill. Surrounded by trees. Tranquility can be found. We are located near the Antique trail of Southbury. Its a 25 min ride to Danbury or 20 min ride to Waterbury. Just under 2 hours to NYC. And a little over 2 hours to Boston. We can provide a daily clean at an additional cost. They are grocery stores, TJ. Maxx and Starbucks within minutes.

Guest favorite

Apartment in Middlebury

4.92 out of 5 average rating, 126 reviews

Cozy Apartment with Water View of Brook

Lower Level Beautiful Space: Well kept with an amazing view of a Beautiful Brook that Runs through the Backyard. It is a small cottage style home and you will have the best views of the Brook. You will also hear and see the Brook from the Bedroom, Kitchenette and Patio. Depending on the season it will Vary. If you have 2 Cars please make sure you let me know so I can accommodate.

Guest favorite

Apartment in Naugatuck

4.87 out of 5 average rating, 60 reviews

Private studio.

Cozy, in safe and quiet neighborhood. So you’ll be able to sleep peacefully. Guest will have comfort and privacy to themselves. This studio is close to several restaurants that you can enjoyed. And few places that offer the perfect escape and so many fun things to do. Nature lovers will find themselves at home will it scenic hiking trails.