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Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guesthouse in Southbury

4.94 out of 5 average rating, 309 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).

Home in Woodbury

4.99 out of 5 average rating, 121 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this sanitized, rambling, relaxing, light-filled 2 story 4 bedroom 2.5 bath on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from 5 popular, fabulous restaurants. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

Guest suite in Watertown

4.92 out of 5 average rating, 183 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!

Guest suite in Bethlehem

4.99 out of 5 average rating, 257 reviews

Breezy Crest private & restful w/antique charm

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 ski slopes.

Rental unit in Litchfield

4.98 out of 5 average rating, 128 reviews

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Home in Bristol

4.91 out of 5 average rating, 151 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Cabin in Sherman

4.97 out of 5 average rating, 347 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Home in Bethlehem

4.97 out of 5 average rating, 286 reviews

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Guest suite in Waterbury

4.86 out of 5 average rating, 228 reviews

Waterbury Cozy, Private In-Law Suite

Cozy and private 1 bedroom apartment/ In-law suite in the basement of a private house with a separate entrance and parking right in front! Guests have the entire space to themselves. Why check-in to a hotel when you can make yourself at home with complimentary parking, WiFi, toiletries, coffee and an Amazon Fire TV Stick. Come enjoy your stay in a beautiful, spacious, sparkling clean, and comfortable apartment in a safe neighborhood.

Rental unit in Bethlehem

4.94 out of 5 average rating, 243 reviews

Cozy 2nd Floor Suite In Bethlehem CT

Our private 2nd floor suite is fully equipped and easy on the budget. Sleeps a single or couple in comfort in queen bedroom. PLEASE NOTE- There is only one bed. This property is not suitable for friends traveling together unless they are willing to share the queen bed. Spacious living room and well-equipped kitchenette. Dedicated workspace. Relax with Wi-Fi, streaming channels. Free calls anywhere in the US.

Guest suite in Wallingford

5 out of 5 average rating, 545 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

Guest suite in Morris

4.99 out of 5 average rating, 379 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Vacation rentals for every style

Get the amount of space that is right for you

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Stylish accommodations and amenities

Unique stays

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Homes

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Popular amenities for Middlebury vacation rentals

Free parking on premises

Air conditioning

Stay near Middlebury's top sights

Quassy Amusement Park & Waterpark38 locals recommend

Hop Brook Lake10 locals recommend

Mill House Antiques8 locals recommend

Dunkin'7 locals recommend

LEBNANI Lebanese Grill5 locals recommend

Vyne Restaurant & Bar4 locals recommend

Other great vacation rentals in Middlebury

Home in Watertown

4.9 out of 5 average rating, 49 reviews

Tiny Home Away From Home - Complete Privacy, Peace

Rental unit in Bethlehem

5 out of 5 average rating, 78 reviews

C&C Rush Haven Farm, A Sanctuary for All Life!

Home in Woodbury

4.95 out of 5 average rating, 94 reviews

Ferris House: Private 19th Century Home

Home in Naugatuck

4.97 out of 5 average rating, 35 reviews

Peace and quite away from home

Guest suite in Plymouth

4.94 out of 5 average rating, 50 reviews

Secluded | Cozy | Nature

Guest suite in Cheshire

4.94 out of 5 average rating, 94 reviews

Cozy & Private Studio Suite

Cabin in Bethlehem

4.95 out of 5 average rating, 63 reviews

Cozy Cabin w/ Fireplace | Near Ski Mountains

Cottage in Bethlehem

4.99 out of 5 average rating, 83 reviews

Cozy Cottage in Litchfield Cty | Pet Friendly

Quick stats about vacation rentals in Middlebury

Total rentals
30 properties
Total number of reviews
1.3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace

Frequently Asked Questions

Do house rentals in Middlebury have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Middlebury. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Middlebury?
Four-legged friends are welcome in Middlebury. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Middlebury have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Middlebury. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Middlebury?
Make yourself at home in Middlebury by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Bunker Hill, and over 110 vacation rentals in Hop Brook.
Are there vacation rentals with a dedicated workspace in Middlebury?
Yes! Work meets play with ease at over 10 vacation rentals in Middlebury featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Middlebury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wireless internet, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore