
Pet-friendly holiday rentals in Roxbury
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Roxbury
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com
PetsOutdoor spacesLocation
4.88 out of 5 average rating, 222 reviews
Your Perfectly Wonderful Woodbury Sanctuary!
Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this rambling, light-filled 2 story 4 bedroom 2.5 bath historic district home on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from popular restaurants and diners. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."
WalkabilityOutdoor spacesLaundry
4.99 out of 5 average rating, 147 reviews
Come and enjoy the BURY's of CT!
Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.
WalkabilityPetsSleep quality
4.95 out of 5 average rating, 106 reviews
Cozy Cottage |Quintessential CT | Pet Friendly
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.
Outdoor spacesPetsFamily
4.99 out of 5 average rating, 173 reviews
Beautiful country house in Cornwall CT.
If you love being in touch with nature, this is a perfect and pleasant place to enjoy with family and friends and wake up to the sound of birds! and enjoy all the seasons of the year. And in winter you can escape 15 minutes to this area of Mohawk paradise and if you are a fishing lover, the House-tonic River is just 5 minutes away, 2 minutes to Kent Falls, 7 minutes to Kent where you can find restaurants and a grocery store! You can enjoy beautiful flower gardens from spring to fall.
Outdoor spacesPetsQuiet
4.98 out of 5 average rating, 105 reviews
Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.
PetsOutdoor spacesNearby
4.99 out of 5 average rating, 148 reviews
(°) The Wandering Peacock (°)
The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.
WalkabilityPetsFamily
4.88 out of 5 average rating, 370 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 two-person kayaks are available for use from May 1 to November 1.
WalkabilityPetsHiking
4.96 out of 5 average rating, 462 reviews
Charming Historic Cottage in the Redwoods
Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.
Outdoor spacesPetsHeating
4.98 out of 5 average rating, 103 reviews
Sleeps 18 LAKE VIEWS! Perfect for large group!
*We only book to 25 or older PERFECT SPOT TO BRING YOUR BOAT! This home sleeps up to 18 people + is perfect for large groups, wedding parties or team retreats. You’ll love the sunset views, large living room and kitchen for entertaining and hanging out, pool table, dart board and large yard for games. There’s even a spot to bring your own boat or jet ski and room to park your trailer! IG stay_at_the_lake
Outdoor spacesPetsLocation
4.93 out of 5 average rating, 141 reviews
Cozy Cottage with Fire Pit, near Beach
Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities.
Outdoor spacesPetsParks
4.96 out of 5 average rating, 232 reviews
Stunning Views, Bucolic Bliss in 1790s Farmhouse
Sweetbrier Farm was built in 1793 and renovated early in the 21st century. The house features 5 bedrooms including a master suite, ample common spaces, huge kitchen, enclosed porch, luxurious pool, and a pond.
PetsWalkabilityCheck-in
4.93 out of 5 average rating, 213 reviewsPopular amenities for Roxbury pet-friendly home rentals
Pet-friendly house rentals

Charming and relaxing 4b farmhouse group getaway
PetsOutdoor spacesCheck-in
4.9 out of 5 average rating, 240 reviews
Slate Cabin - Stylish Country Escape x Rhinebeck
PetsOutdoor spacesAmenities
4.98 out of 5 average rating, 132 reviews
Beautifully Restored Barn With New England Charm
Outdoor spacesWalkabilityParks
4.96 out of 5 average rating, 355 reviews
Cozy house w/ screened porch near Kent & falls
PetsWalkabilityWi-Fi
4.97 out of 5 average rating, 112 reviews
The Waterfall House
WalkabilityOutdoor spacesGetting around
4.96 out of 5 average rating, 240 reviews
Cozy Family Home - Kid & Pet Friendly
WalkabilityPetsIndoor spaces
4.92 out of 5 average rating, 241 reviews
County Seat Colonial/Walk to Town-HOST&Co
Outdoor spacesPetsSleep quality
5.0 out of 5 average rating, 128 reviews
Lux Bungalow on the Lake
WalkabilityOutdoor spacesNearby
4.93 out of 5 average rating, 231 reviewsPet-friendly home rentals with a pool

Huge eclectic space w/fireplace. 1.5hr to city
WalkabilityPetsBarbecue
4.97 out of 5 average rating, 225 reviews
Peaceful Light-Filled Guesthouse salt pool/sauna
Outdoor spacesWalkabilityEV charging
5.0 out of 5 average rating, 190 reviews
Modern Upstate Cabin, near Rhinebeck NY
PetsWalkabilityIndoor spaces
4.96 out of 5 average rating, 397 reviews
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
PetsOutdoor spacesTV
4.95 out of 5 average rating, 137 reviews
The Cottage by the Lake: Hudson Valley Indulgence
PetsWalkabilityAccuracy
4.99 out of 5 average rating, 330 reviews
Sackett & Van Dam Guest House @ Little 9 Farm 1706
PetsWalkabilityComfort
4.98 out of 5 average rating, 178 reviews
Magic Red Barn with Heated Salt Pool (opened now)
Outdoor spacesPetsQuiet
4.96 out of 5 average rating, 145 reviews
Eco Cottage in the Woods
Outdoor spacesPetsBackyard
4.93 out of 5 average rating, 204 reviewsPrivate, pet-friendly home rentals

The Treehouse Lovenest
Outdoor spacesWalkabilityCondition
4.84 out of 5 average rating, 520 reviews
Suite Hill Studio
Outdoor spacesPetsRiver
4.85 out of 5 average rating, 122 reviews
Cozy Apartment with Water View of Brook
PetsWalkabilityCondition
4.94 out of 5 average rating, 169 reviews
Top Side
Outdoor spacesWalkabilityDecor
5.0 out of 5 average rating, 148 reviews
Serenity in the Roxbury Woods!
Outdoor spacesPetsSleep quality
4.87 out of 5 average rating, 31 reviews
NEW! Luxury Barn with Panoramic Views
QuietIndoor spacesGetting around
5.0 out of 5 average rating, 13 reviews
The Art House: 5-Acre Getaway w/ AC & Firepit
Outdoor spacesWalkabilityAccuracy
5.0 out of 5 average rating, 50 reviews
Peaceful 3BR Getaway
PetsOutdoor spacesHiking
5.0 out of 5 average rating, 17 reviewsDestinations to explore
- Yale University
- Bear Mountain State Park
- Six Flags New England
- Fairfield Beach
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Storm King Art Center
- Taconic State Park
- Sunken Meadow State Park
- Mohonk Preserve
- Kent Falls State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Compo Beach
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Millbrook Vineyards & Winery
- Storm King Art Center
- Sherwood Island State Park
- Ski Sundown





