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, 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

Top guest favorite

A covered outdoor seating area features a combination of woven chairs and a sofa arranged around a stone floor. Soft lighting is provided by string lights overhead, while rustic wooden beams and walls create a warm, inviting backdrop.

Guesthouse in Southbury

4.93 out of 5 average rating, 322 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).

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, 195 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, 299 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, 44 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, 114 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

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.

Top guest favorite

A bright and airy living area features a comfortable seating arrangement with a grey sofa, accented by decorative cushions. Natural light enters through multiple large windows, highlighting the rich wooden floor. A desk and ergonomic chair are positioned alongside a window, creating a functional workspace.

Home in Roxbury

5 out of 5 average rating, 17 reviews

Bright Mid-Century Modern Retreat-90 min from NYC

Mid-Century Modern, newly renovated 3 bedroom, 2.5 bath located on a secluded road. Inground heated pool & mature landscaping. Enjoy Sonos inside and out. Light shines into the living room, vaulted ceiling, wall of windows and sliders to a wooden deck overlooking the pool. Dining room with floor-to-ceiling windows and skylights. 2 bedrooms and 2 full baths on the main level; a 3rd bedroom with balcony, and a half bath. Electric charging station. Pool is open for the season.

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, 280 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.

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, 120 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.

Top guest favorite

The exterior of a two-story house is shown, featuring a covered porch with seating and planters. Lush greenery surrounds the property, including shrubs and flowering plants. A rustic shed is visible in the background, adding charm to the tranquil setting.

Guest suite in Washington

5 out of 5 average rating, 64 reviews

Custom industrial farmhouse Apt in Washington Dpt

Cozy and quiet one bedroom suite with a full kitchen. This space is on the 2nd floor over an attached garage with an entrance separate from the main house. It is newly constructed and has its own heat and AC, complete kitchen, full bath with shower and king sized bed. Just around the bend from Steep Rock Land Preserve and walking trails, and convenient to the center of town with galleries, restaurants and shops.

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Popular amenities for Roxbury vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Roxbury

Superhost

A decorative stone turtle sculpture rests on a wooden floor, complementing a potted plant placed in a metal stand. The turtle is crafted from smooth, multi-colored pebbles, adding a touch of natural texture to the space.

Cottage in Bethlehem

5 out of 5 average rating, 3 reviews

Lakefront Charming Cottage Retreat

RicardoRating, 5 stars2 weeks ago

The Lake House was a great choice to stay! Everything went smooth from arrival till departure. We didn't have a single issue during our stay. The house was perfectly clean and very complete. It offered everything we needed. The view over the lake is fantastic and ease of access to the water for kayaking. We had a great time here, and would definitely stay here again.

Superhost

A spacious house is set against a backdrop of dense greenery, featuring large windows that offer abundant natural light. The outdoor area includes a deck with seating and a covered space, surrounded by well-kept gardens and open lawn.

Place to stay in New Milford

4.74 out of 5 average rating, 27 reviews

Large, comfortable, sunny space

John PaulRating, 5 stars5 days ago

Thanks for a kind and helpful stay. A calm peaceful garden spot to stay in the area.

A modern living area features a large circular coffee table surrounded by a plush sofa and a contrasting area rug. Tall windows allow natural light to filter in, while a series of pendant lights hang above. A dining table is positioned nearby, creating a functional gathering space.

Guesthouse in Roxbury

4.75 out of 5 average rating, 4 reviews

Modern Country

Jennifer FlynnRating, 5 stars3 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.

Superhost

A bear is seen crossing a quiet, tree-lined road. Green foliage surrounds the area, and a stop sign stands nearby, indicating the presence of a residential or rural setting. Sunlight filters through the leaves, creating a soft illumination of the scene.

Home in Watertown

4.8 out of 5 average rating, 44 reviews

Cozy Cottage

KatieRating, 5 stars2 weeks ago

This was the perfect place to relax after visiting family all day. Hector's place was clean, private, and peaceful. the drive way is a little hard to find but GPS will get you there fine. The airbnb had everything we needed and loved the back deck for grilling. highly recommend.

Guest favorite

Home in Roxbury

5 out of 5 average rating, 65 reviews

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.

Top guest favorite

A gentle horse is seen among a field of daisies, creating a serene scene against the backdrop of a dark barn with a distinctive white cross pattern on the door. The horse's mane is slightly windswept, enhancing the tranquil atmosphere.

Guesthouse in Washington

5 out of 5 average rating, 10 reviews

Large studio cottage on horse farm

KellyRating, 5 stars2 months ago

Catharine was a great host! The cottage was so cute and exactly what was pictured. She was great and responsive and even let us feed the horses and pet them. It was a beautiful property and a great place to stay just a quick drive to Washington and we got to see Pos cafe and the Mayflower Inn and it was a quick twenty min drive to New Milford where we were attending a Gilmore Girls convention. The WiFi was great and super important because there is no service in that area. I would definitely stay here again.

Top guest favorite

Home in Newtown

5 out of 5 average rating, 5 reviews

Rustic farmhouse in the country, walk to village!

EmilyRating, 5 stars1 week ago

A beautiful space to gather with friends for a quick weekend getaway!

Top guest favorite

A modern coffee maker is positioned on a dark granite countertop, featuring a transparent water reservoir on one side and a stainless steel carafe on the other. The sleek design includes a black handle and a power button, complemented by a glossy white tiled backsplash.

Guesthouse in Washington

5 out of 5 average rating, 40 reviews

Private, cozy woodland getaway.

JingRating, 5 stars3 weeks ago

This charming cabin is an absolute hidden gem - a true sanctuary that offers both serene tranquility and thoughtful comforts. Clare's responsiveness and warm hospitality made us feel instantly welcome, especially when we discovered the delightful homemade treats awaiting our arrival. The cabin's proximity to our kid's school made it incredibly convenient for quick meet-ups and cozy breaks between schedules. We loved how the space effortlessly blended rustic charm with modern comforts, creating that perfect 'home away from home' feeling. Every detail reflected Clare's considerate hosting style. We'll definitely be returning!

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Vacation rentals in Roxbury

Top-rated vacation rentals in Roxbury

Vacation rentals for every style

Popular amenities for Roxbury vacation rentals

Other great vacation rentals in Roxbury

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