Vacation rentals in Roxbury

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Top-rated vacation rentals in Roxbury

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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, 149 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

A serene backyard scene is captured, featuring a swimming pool surrounded by lush greenery. Lounge chairs are positioned nearby under the sun, providing a relaxing space. Clear blue water reflects the sky above, with people engaged in various activities within the pool.

Barn in Roxbury

4.97 out of 5 average rating, 39 reviews

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.

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, 304 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!

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 couple sits on a plaid blanket in the bed of a truck, accompanied by a dog. Lush green trees create a natural backdrop, and the tranquil setting suggests a peaceful outdoor atmosphere.

Farm stay in New Milford

5 out of 5 average rating, 115 reviews

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!

Guest favorite

Cottage in Bethlehem

4.98 out of 5 average rating, 107 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

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 favorite

A serene outdoor setting features several Adirondack chairs arranged around a fire pit, surrounded by lush green trees and natural rock formations. The calm river flows gently nearby, with sunlight filtering through the canopy, creating a peaceful retreat atmosphere.

Cottage in Weston

4.97 out of 5 average rating, 143 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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, 204 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 spacious living area features large windows that allow natural light to fill the room. A comfortable brown sectional sofa is complemented by a white coffee table, adorned with books and decorative items. Plants are positioned nearby, adding a touch of greenery to the space.

Home in Roxbury

4.91 out of 5 average rating, 22 reviews

Serenity in the Roxbury Woods!

Perfect cozy hideaway for families, writers, artists, couples, digital nomads or anyone seeking a peaceful, serene retreat in the woods! Set at the end of a private street, far back from the road, lies your 3BR, 2.5BA oasis with every amenity you can ask for! High-end appliances, blazing-fast wifi, soaking tub, Viking/Subzero chef's kitchen, all set on 8 quiet acres. The only sound you'll hear is the birds (and the occasional coyote howl at night). Inquire today!

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.

Superhost

Cabin in Roxbury

4.89 out of 5 average rating, 18 reviews

Roxbury Cabin Retreat

Take it easy at this unique and tranquil getaway. Escape to this charming cabin nestled on 10 acers of tranquil Roxbury, CT woodland. Tucked away down a secluded gravel road, this rustic retreat offers a peaceful escape from the hustle and bustle of city life. Enjoy the serenity of nature, unwind on the porch, and explore the surrounding woods. Perfect for a quiet getaway or a romantic retreat.