Holiday rentals in Bridgewater

4.98 out of 5 average rating, 148 reviews

Home in Brookfield

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

4.97 out of 5 average rating, 39 reviews

Barn in Roxbury

Classic Red Barn with game room

Enjoy a fun and romantic stay in this renovated classic red barn on a private country property. The barn is only available when the main house is unoccupied, so you will have the whole barn, with game and fitness rooms, and the full run of the beautiful private country exterior property. If you're lucky, you'll get a visit from the horses at the neighboring horse farm! The barn's game room has a couch, ping pong and pool tables, basketball hoop outside, and a separate exercise and boxing space.

5 out of 5 average rating, 22 reviews

Flat in Southbury

New Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, smart TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to 84

4.91 out of 5 average rating, 195 reviews

Guest suite in Watertown

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!

4.99 out of 5 average rating, 299 reviews

Guest suite in Bethlehem

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!

5 out of 5 average rating, 44 reviews

Barn in Roxbury

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.

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.

5 out of 5 average rating, 114 reviews

Farm stay in New Milford

Farm House

A serene get away in a farm cottage on a real working farm. We homesteaded this property in 2012 and have created our own slice of paradise. We grow produce and flowers we sell at a local farmers market. We have Scottish Highlander cows, an ex racehorse, a shetland pony, goats, ducks, chickens, barn cats and a resident farm dog, Finula. You're welcome to roam the property, sit by the pond, visit with the animals, take a tour of the farm or explore all that Litchfield county has to offer!

4.95 out of 5 average rating, 203 reviews

Cottage in New Milford

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.

4.92 out of 5 average rating, 281 reviews

Flat in Brookfield

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.

4.99 out of 5 average rating, 121 reviews

Home in Southbury

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.

5 out of 5 average rating, 31 reviews

The Art House: 5-Acre Getaway w/ AC & Firepit

Situated on 5 acres, "The Art House" is the perfect place for those looking to relax and unwind, as well as to explore and enjoy all that the area has to offer. This contemporary farmhouse, tucked away on a private hilltop in the beautiful New England countryside, offers breathtaking sunset views, as well as a spacious interior that has been thoughtfully decorated, and desirable amenities that allow guests to feel right at home.

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Other great holiday rentals in Bridgewater

4.89 out of 5 average rating, 38 reviews

Chalet in New Milford

Candlewood Lake Vacation Home | jj chalet

JulienRating, 5 stars2 weeks ago

We had an excellent stay at Jessica's! The house is beautiful, clean and comfortable. And of course quiet owing to the location. There is a forest right behind which was perfect for exploration with the kids. A 5-minute walk took us to an absolutely gorgeous scenery with a pond, fields and forest, from which lovely walks are available. We also enjoyed the kayaks on the lake nearby. All this is in a very peaceful and quiet environment. Jessica's communication was perfect, she was very responsive and helpful and kindly let us check out late on the last day. If you come with young kids, bear in mind the steep stairs and lots of fragile items/art in the house.

5 out of 5 average rating, 8 reviews

Home in New Milford

Cozy cottage

JamesRating, 5 stars1 week ago

I have never had a bad Airbnb experience and I have even had a couple that were the best, better then what one could expect. This Airbnb is the Best in which I have ever stayed. One finds a place that matches its description and more. Outfitted for anything one would need when traveling, The place is extremely well maintained, everything works, great WIFI, and the hosts were instantaneously communicative, pro-active and responsive.

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!!

Guest house in Roxbury

4.75 out of 5 average rating, 4 reviews

Modern Country

Jennifer FlynnRating, 5 stars4 weeks 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.

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

4.98 out of 5 average rating, 59 reviews

Guest house in Newtown

Guest Suite at Wisteria Gardens

JuliaRating, 5 stars2 weeks ago

We really enjoyed our stay at this adorable and cozy Airbnb. Our one-year-old loved seeing the chickens and goats, and we found the area peaceful. Everything about the Airbnb was excellent — clean, beautifully decorated, with lots of thoughtful touches.

5 out of 5 average rating, 65 reviews

Home in Roxbury

Twilight Dreams Farm

AlexRating, 5 stars6 months ago

Charming farmhouse on a vast property. Anne is a wonderful host, very communicative and easy to deal with. She was kind enough to show our kids around the farm and teach them a bit about ducks. The surrounding area is lovely. All in all this place worked out great for us.