Vacation rentals in Bridgewater

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Top-rated vacation rentals in Bridgewater

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Guest favorite

A covered front porch features wooden flooring and is framed by dark columns. Two rustic wooden chairs are positioned beside a small table, creating a space for relaxation. Surrounding greenery is visible, enhancing the natural setting.

Apartment in Amenia

4.92 out of 5 average rating, 106 reviews

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Top guest favorite

A charming house with a mix of stone and siding is presented, surrounded by lush greenery and trees. The two-story structure features a prominent stone chimney. A pathway leads from the front yard, creating a welcoming entrance to this serene setting.

Home in Brookfield

4.98 out of 5 average rating, 148 reviews

Stay at Old Dorset Farm & create lifelong memories

This 1905 Historic Old Bakery is the perfect location to create lifelong memories while exploring quaint New England. Set on 4 acres, with a lake, trails and golden rolling hills just minutes away, you’ll enjoy all of New England's beauty. Hiking, kayaking, antiques shopping or gallery visiting... it can all be done right here. But you don't have to go anywhere. The two fireplaces invite you to just stay, relax and enjoy the complimentary bottle of Prosecco. Follow us on Insta: @Old_Dorset_Farm

Guest favorite

The bathroom features warm orange walls and a tiled floor. A white toilet is positioned against one wall, with a mounted toilet paper holder nearby. Two dark wooden shelves are installed above a sleek countertop, providing space for toiletries or storage.

Guest suite in Watertown

4.91 out of 5 average rating, 196 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

A cozy living space features a patterned sofa adorned with various throw pillows. Nearby, a light-colored stool complements a wooden coffee table, while a textured area rug adds warmth to the room. Decorative woven baskets are displayed on the wall above the sofa.

Guest suite in Bethlehem

4.99 out of 5 average rating, 301 reviews

Breezy Crest cozy, private retreat 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!

Superhost

The exterior of a dark blue barn cottage is displayed, featuring a pink door and several small windows. A seating area with bright red chairs is positioned on a leaf-covered lawn, surrounded by trees and greenery.

Guesthouse in Dover Plains

4.87 out of 5 average rating, 115 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Top guest favorite

A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.

Barn in Roxbury

5 out of 5 average rating, 45 reviews

Fully Renovated Rural Barn

Newly renovated barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking in a dedicated driveway.

Top guest favorite

A small bedroom features a black metal bed frame with a striped bedspread and decorative pillows. Two bedside tables with lamps provide illumination. Natural light enters through a window, while map prints are displayed on the wall. Soft seating is offered by two poufs.

Home in Bridgewater

5 out of 5 average rating, 17 reviews

Mid-Mod 2BR Cottage in CT Woods

Escape the city and come relax in this newly renovated, mid-century modern getaway in the Litchfield Hills. A well-appointed two bedroom, one full bath split-level cottage with a stylish living room and fully stocked kitchen serves as your home base to explore all the rural charms that New England has to offer. Farm fresh produce and lake dips in the summer, apple picking and hiking through fall foliage, winter skiing and spring flowers - every season in CT brings something new to enjoy.

Guest favorite

A handcrafted wooden staircase features unique railing posts made from natural branches. The rustic feel is enhanced by warm wood paneling that surrounds the staircase. A window allows natural light to filter in, illuminating the organic textures and shapes of the wood.

Cottage in New Milford

4.95 out of 5 average rating, 203 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Guest favorite

A rustic cabin is nestled among tall trees, showcasing natural wood siding and a stone chimney. Warm light glows from the windows, creating a cozy atmosphere against the backdrop of lush greenery. The entrance is framed by rich foliage and rocky ground.

Cabin in Sherman

4.97 out of 5 average rating, 391 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..

Guest favorite

A rustic game room features wooden walls with a rich texture, complemented by a pool table at the center. A long table lined with benches offers seating, while various artworks are displayed on the walls. Soft lighting adds to the inviting ambiance.

Apartment in Brookfield

4.92 out of 5 average rating, 282 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favorite

The exterior of the stone cottage is framed by lush autumn foliage. A spacious wooden deck features several lounge chairs, providing a relaxing outdoor space. The entrance is marked by a subtle stone pathway, enhancing the inviting appeal of the cottage.

Cottage in Pawling

4.98 out of 5 average rating, 124 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite

A small outdoor patio area features a round glass table surrounded by two black wicker chairs. The space overlooks a grassy area with lush trees in the background, creating a serene environment for outdoor relaxation.

Home in Southbury

4.99 out of 5 average rating, 121 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.

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Popular amenities for Bridgewater vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Bridgewater

A metal chair sits on a stone patio by the riverbank, surrounded by lush greenery. The calm water of the Pomperaug River flows gently nearby, creating a serene backdrop for relaxation.

Cabin in Southbury

4.75 out of 5 average rating, 215 reviews

River Stone Hollow

DanielleRating, 5 stars2 weeks ago

Kara was really wonderful with communication, it was a little hard to find simply because the road looks like someones driveway but after I passed it I realized where it was and found it easily after the. Sadly it rained all weekend so we didn't get to enjoy the back patio/River like we wanted to but the inside space was comfy and accomodating for a rainy day. The diner up the road was great and there were nearby restaurants/stores. Overall good stay (minus the mosquitoes! but that comes with a River haha). I would recommend the diner up the road and Bevy had good ambiance and food as well.

Top guest favorite

A bright dining room features a large wooden table surrounded by multiple chairs. Glass doors offer views of the greenery outside, while a chandelier hangs from the ceiling's exposed beams. Natural light fills the space, enhancing the rustic charm.

Home in Bridgewater

5 out of 5 average rating, 5 reviews

Hat Shop House. Family friendly

MargoRating, 5 stars5 months ago

Beautiful house and surroundings. Fit our 2 families perfectly and was well stocked with all our needs. Great yard to play! Hosts are very responsive and welcoming. We loved our stay and would come again!!

Guesthouse in Roxbury

4.75 out of 5 average rating, 4 reviews

Modern Country

Jennifer FlynnRating, 5 stars1 month ago

Stunning guesthouse in the rolling hills of NW CT. Well stocked, luxurious linens, privacy abounds with the comfort of friendly hosts. A perfect home away from home for regional exploring. Excellent hiking in the area, quaint shops, and farm to table dining. Recommend Hollister House Garden for self guided garden tours.

Guest favorite

A pig stands at the water's edge, partially submerged in a small pond. Surrounding vegetation includes lush green leaves and rocks, some covered in moss. The animal's textured coat displays shades of brown and gray, while bright yellow tags are visible on its ear.

Farm stay in Brewster

4.84 out of 5 average rating, 68 reviews

Crooked Cottage at Lobster Hill Farm

KileyRating, 5 stars1 month ago

Cute cottage with a rustic camp feel. The front porch is a relaxing hangout spot overlooking a variety of small farm animal enclosures. State lands next door offer a decent place to walk around, and the place is a short drive from town where you can find a variety of restaurants.

A tranquil backyard scene showcases a clear salt-water pool reflecting blue skies and lush greenery. A pink flamingo float rests in the water, while two lounge chairs are positioned nearby. The farmhouse and patio seating area are visible in the background, surrounded by trees.

Home in Bridgewater

5 out of 5 average rating, 4 reviews

Farmhouse Chic

LucasRating, 5 stars8 months ago

This is a great place. 1800s house with rooms and rooms full of incredible details both original and modern. Plenty of bedrooms and bathrooms and even a pool! The area has a dreamlike New England vibe esp in the Fall. Plenty of privacy. Easy access. All amenities. Five stars

Top guest favorite

Guesthouse in Newtown

4.98 out of 5 average rating, 63 reviews

Guest Suite at Wisteria Gardens

PeterRating, 5 stars1 week ago

So peaceful, so comfortable and just the nicest hosts. And there are goats!! Just a perfect little place to spend a quiet night off the road. Beautifully tucked away off the beaten path and Christine is so nice and welcoming. She even had to-go coffee cups for our early morning departure. Very nice touch. Highly recommend!

Top guest favorite

A spacious area features large sliding glass doors leading to a private deck with two chairs. Natural light fills the space, enhancing views of the surrounding forest. Two windows on either side frame the outdoor scenery, creating an inviting atmosphere.

Apartment in Pawling

5 out of 5 average rating, 88 reviews

Quiet Studio Apartment in Pawling

Yeon-SooRating, 5 stars3 days ago

The studio is one of the cleanest Airbnbs I’ve ever stayed in. It was spotless, and I felt no need to wipe anything down before unpacking -- always an excellent way to start a stay. Although attached to the main house, it’s very private and feels secluded. The location is also very convenient -- just a short drive from the main part of town with excellent dining options. Don is excellent with communication, and I would love to stay again!

Top guest favorite