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.

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Guest favourite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck

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
Top Guest favourite
Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.
Home in Woodbury

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
Guest favourite
A cozy living room features a stone fireplace with a mounted television above. Natural light enters through a large window, accented by sheer curtains. A plush rug covers the floor, surrounded by a sectional sofa and a chair, offering a comfortable gathering space.
Home in Waterbury

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
Top Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem

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
Top Guest favourite
Cabin in Cornwall

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
Top Guest favourite
Home in Newtown

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
Top Guest favourite
A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.
Farm stay in Kent

(°) 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
Top Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

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
Top Guest favourite
A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.
Farm stay in Redding

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
Superhost
A spacious deck is furnished with several striped lounge chairs surrounding a central table. Soft glow lights are suspended overhead, illuminating the area. A panoramic view of the lake and vibrant sunset colors create a serene setting for relaxation and social gatherings.
Home in Brookfield

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
Top Guest favourite
Home in Fairfield

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
Guest favourite
A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.
Home in Litchfield

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 reviews

Popular amenities for Roxbury pet-friendly home rentals

Pet-friendly home rentals with a pool

Guest favourite
A rustic stone fireplace is showcased, featuring a roaring fire that provides warmth and ambiance. A wooden bench sits in front, while logs are neatly stacked beside the hearth. Colorful artwork is displayed above the mantel, enhancing the charm of the space.
Guest suite in Holmes

Huge eclectic space w/fireplace. 1.5hr to city

WalkabilityPetsBarbecue

4.97 out of 5 average rating, 225 reviews
Top Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

Outdoor spacesWalkabilityEV charging

5.0 out of 5 average rating, 190 reviews
Top Guest favourite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

PetsWalkabilityIndoor spaces

4.96 out of 5 average rating, 397 reviews
Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

PetsOutdoor spacesTV

4.95 out of 5 average rating, 137 reviews
Guest favourite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

PetsWalkabilityAccuracy

4.99 out of 5 average rating, 330 reviews
Top Guest favourite
The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.
Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

PetsWalkabilityComfort

4.98 out of 5 average rating, 178 reviews
Guest favourite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Outdoor spacesPetsQuiet

4.96 out of 5 average rating, 145 reviews
Top Guest favourite
A bright living room features a sofa facing large glass doors that open to a view of the forest. A cozy armchair is situated nearby, along with a simple coffee table. A bookshelf contains various items, and a wood stove is positioned in the corner.
Guesthouse in Stanfordville

Eco Cottage in the Woods

Outdoor spacesPetsBackyard

4.93 out of 5 average rating, 204 reviews