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Vacation rentals in Roxbury

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Top-rated vacation rentals in Roxbury

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Brookfield

4.98 out of 5 average rating, 136 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

Guesthouse in Southbury

4.94 out of 5 average rating, 309 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 suite in Watertown

4.92 out of 5 average rating, 183 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!

Guest suite in Bethlehem

4.99 out of 5 average rating, 257 reviews

Breezy Crest private & restful w/antique charm

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 ski slopes.

Guesthouse in Dover Plains

4.89 out of 5 average rating, 104 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!

Cabin in New Milford

4.95 out of 5 average rating, 175 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.

Home in New Fairfield

4.93 out of 5 average rating, 107 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Rental unit in Litchfield

4.98 out of 5 average rating, 128 reviews

Artist's Garden Apartment

Private second floor apartment with entrance. Detached from the host's main house. Overlooks perennial herb and flower gardens located in the backyard. Walking distance to White Memorial Nature Preserve and the historic Litchfield Center. Walk or bike from the backyard to shopping, restaurants, art galleries, bakeries, or to a 3000 acre nature preserve and take in the Flora and Fauna. Quiet residential neighborhood that is close to so many amenities and activities.

Guesthouse in Gaylordsville

4.97 out of 5 average rating, 105 reviews

Adorable Cottage in Pastoral Setting

"Farm Cottage" is a charming and comfortable one bedroom cottage apartment that is tucked back in its own private pastoral setting alongside a farm. The cottage is ideally situated between the towns of Kent and New Milford, with easy access to all local attractions. Beautifully furnished with a mixture of antiques and vintage furnishings, the cottage offers a large deck overlooking a rolling meadow plus a full kitchen and washer/dryer. Ideal for one-two guests.

Cabin in Sherman

4.97 out of 5 average rating, 347 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, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Home in Bethlehem

4.97 out of 5 average rating, 286 reviews

Litchfield County Farmhouse with a Modern Twist

Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Cottage in Pawling

4.98 out of 5 average rating, 106 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.

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Popular amenities for Roxbury vacation rentals

Free parking on premises

Air conditioning

Stay near Roxbury's top sights

The Institute For American Indian Studies12 locals recommend

Mine Hill Preserve11 locals recommend

Woodbury Ski Area5 locals recommend

Maple Bank Farm4 locals recommend

Roxbury Market & Deli LLC4 locals recommend

Mine Hill Distillery3 locals recommend

Other great vacation rentals in Roxbury

Guesthouse in Roxbury

5 out of 5 average rating, 16 reviews

Modern Country

Guesthouse in New Milford

5 out of 5 average rating, 22 reviews

Cozy House in the Trees w/ Fireplace

Home in New Fairfield

4.94 out of 5 average rating, 16 reviews

Escape to a Celebrity Chef's Waterfront Sanctuary

Guesthouse in Newtown

4.93 out of 5 average rating, 72 reviews

Farm Cottage

Home in Bridgewater

5 out of 5 average rating, 19 reviews

The Art House: 5-Acre Private Getaway w/ Firepit

Guesthouse in Sharon

4.99 out of 5 average rating, 95 reviews

Cottage with a Waterfall View

Home in Roxbury

4.96 out of 5 average rating, 28 reviews

Zoom In 5* Town Roxbury "Moosehorn" PoshPadsCT

Guesthouse in Washington

5 out of 5 average rating, 31 reviews

Private, cozy woodland getaway.

Quick stats about vacation rentals in Roxbury

Total rentals
30 properties
Nightly prices starting at
$80 before taxes and fees
Total number of reviews
590 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Do house rentals in Roxbury have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Roxbury. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Roxbury?
Yes! Work meets play with ease at over 20 vacation rentals in Roxbury featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Roxbury?
Roxbury has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Roxbury?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Roxbury have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Roxbury. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Roxbury have wifi?
Absolutely! We offer over 20 house rentals with wifi in Roxbury. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Roxbury?
Four-legged friends are welcome in Roxbury. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Roxbury?
Experience the best of Roxbury with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Roxbury vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Roxbury, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Roxbury have free parking?
Absolutely! We offer over 20 house rentals with free parking in Roxbury. Enjoy a tailored experience with all the comforts you desire.

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