Holiday houses in Middlebury

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Top-rated holiday rentals in Middlebury

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Guest favourite
Home in Waterbury
4.96 out of 5 average rating, 144 reviews

Amazing views of the Brass City

East Mountain Views at its finest. This clean, 3-bedroom updated ranch is centrally located to highways and shopping centers. Walk out to the back deck and experience some of the best views of Waterbury including Fireworks from the back deck (July). Wi-Fi/cable, central AC/hot air, washer/dryer, and patio furniture/grill (seasonal) are included with the stay. Plenty of entertainment (board games, corn hole, foosball, air hockey) are provided. This house is truly relaxing and will feel like home.

Top Guest favourite
Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.
Home in Woodbury
4.99 out of 5 average rating, 142 reviews

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this rambling, light-filled 2 story 4 bedroom 2.5 bath historic district home on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from popular restaurants and diners. 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 favourite
A lakeside patio is depicted, featuring several metal chairs arranged around a firepit. Two swinging chairs hang from a pergola, while a dock with a boat and kayak is visible on the water. A vibrant American flag flutters in the background.
Guest suite in Newtown
4.92 out of 5 average rating, 106 reviews

waterfront on Lake Zoar[ SUITE]

Enjoy your private patio overlooking the lake, Or just walk 12 steps to water Edge and visit the cozy lower level and enjoy the swings . Use our kayaks, and don’t forget to bring your fishing pole, go swimming ,or just sit in the sun with a book and listen to the waterfall and you are welcome to sit by the firepit Optional boat dock space, parking Hosts live upstairs Two miles to quaint Sandy Hook center with grocery and restaurants All quests must be register Ninety minutes to Boston/nyc

Guest favourite
A comfortable living space is presented, combining a light-colored sofa and a larger grey sectional couch. A wooden coffee table sits centrally, with artwork displayed on the wall above. Soft lighting is provided by overhead fans, enhancing the cozy atmosphere.
Guest suite in Waterbury
4.88 out of 5 average rating, 159 reviews

Private cozy getaway

Take a break and unwind at this peaceful oasis. Separate entrance for privacy, queen bed, pull out sofa, roll away cot, jacuzzi tub, extra large shower. Location is perfect, minutes from Hawks landing golf course, Post University, Brass mill mall, Metro north, Saint Mary and Waterbury hospital. **Please leave the house in the same condition! No bubbles or anything inside jacuzzi! **Septic system -Do not flush anything but toilet paper** NO Tampons, pads Paper towels Trash Baby wipes

Top Guest favourite
A spacious living area is presented with a large flat-screen TV mounted on a white entertainment unit. A soft gray sofa sits nearby, and a decorative area rug enhances the room's aesthetic. Natural light streams in through a front door adorned with a glass panel.
Guesthouse in Watertown
4.93 out of 5 average rating, 107 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 favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem
4.99 out of 5 average rating, 154 reviews

Cozy Cottage |Quintessential CT | Pet Friendly

Escape to the Cottage at the Grove - with a cozy wood burning fireplace and inviting sectional it is the perfect winter sanctuary. Well equipped with all the amenities; from a fully stocked kitchen to bath salts for the deep soaking tub. One bedroom w/ en-suite bath & pull-out full size sofa bed. Just 30 min to Mohawk or Southington Ski Mountains. Just 10 min to downtown Litchfield, close to local farms & vineyards. For security we have two exterior cameras facing the door & driveway.

Top Guest favourite
The exterior of the two-story home is showcased, featuring a light-colored facade with multiple gabled roofs. A well-maintained lawn surrounds the house, accented by blooming shrubs. A paved driveway leads to a two-car garage, and trees provide a natural backdrop.
Apartment in Waterbury
4.99 out of 5 average rating, 123 reviews

Everything you need! Full Apartment!

Bright and private, this 2nd-floor apartment has everything you need! Features a full kitchen, laundry, and easy highway access. Located on a quiet cul-de-sac near great local bars and restaurants. Enjoy Wi-Fi, Netflix, Prime, and Hulu. Dedicated parking is behind the left garage. FYI: I host card games in the garage below until 11:30 PM, but my guests won't use the driveway. Plus, feel free to use the grill and small patio behind the garage! A cozy, homey retreat for your stay.

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 435 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, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Top Guest favourite
A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.
Home in Southbury
4.99 out of 5 average rating, 156 reviews

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. The holidays are right around the corner. Holiday reservations have date restrictions. Please inquire about availability. 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.

Top Guest favourite
A bright sleeping area features a spacious bed with light blue bedding. A cozy seating area includes a gray sofa and a decorative chair beside a small coffee table. Natural light enters through a window dressed in turquoise curtains, with a television mounted on the wall.
Apartment in Middlebury
4.94 out of 5 average rating, 156 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 favourite
A welcoming living area is shown, featuring two comfortable sofas arranged around a round coffee table with a decorative plant atop. Light streams in through large windows dressed with patterned curtains, complementing the wood flooring and neutral color palette.
Home in Waterbury
4.85 out of 5 average rating, 103 reviews

Clean, quiet 3-bedroom raised ranch (entire house)

Clean, quiet 3-bedroom raised ranch. This property boasts a newly updated kitchen and main-level bathroom. The business center is located in the lower-level for individuals who would like a space to work from "home". All three bedrooms have flat-screen, smart TVs and black out curtains. There is a deck and patio for quiet evenings outside, perfect for grilling.

Top Guest favourite
The living area features a large leather sectional sofa arranged around a wooden coffee table, with a cozy area rug beneath. Natural light pours in through multiple windows, highlighting the exposed log beams on the ceiling and the warm wooden walls.
Cabin in Harwinton
4.97 out of 5 average rating, 100 reviews

Beautiful Brook-side Log Cabin on 3 Private Acres

Fall asleep to the sound of the rushing brook in this beautifully restored log home. The cabin sits in the middle of three wooded acres overlooking Catlin Brook as it cascades through the gorge below. It seems like wilderness, yet all the amenities of Harwinton are just a few minutes away.

Popular amenities for Middlebury holiday rentals