Pet-friendly vacation 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 favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 318 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

Home in Millerton

4.92 out of 5 average rating, 399 reviews

Mountaintop Skyloft

This glorious Silver Mountain SKYLOFT is perfect for a getaway; equipped with hi-speed WiFi (429 mbps) and 60" HD TV. Huge private deck amid the treetops, with 100's of acres of tranquility and privacy Enjoy a romantic evening by the wood burning fire. Jupiter and Mars in the Spring sky. Lots of trails for hiking. Local gourmet food bistro & organic farm market nearby. Just 7 miles from Millerton antiques and cafe. Pets welcome- extra $65/pet/stay (Sofa bed @$99/person/night after 2 )

Top guest favorite

Home in New Milford

4.97 out of 5 average rating, 106 reviews

Idyllic retreat on the water <1.5 hrs to NYC.

Private getaway on 3+ acres on the river with no visible neighbors, sit by the river or in the enclosed patio with view of the water, walk the trails in the area. Great for short escapes or longer discounted stays enjoy great restaurants, antiquing, swimming, hiking, and access to all New England has to offer. In spring, summer and fall lots of open air activities to be had. Fishing, boating, farmers markets and flea markets. In winter many nice walks to be had, skiing is not too far away.

Top guest favorite

Apartment in Pine Plains

4.98 out of 5 average rating, 167 reviews

Newly renovated cutie

Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Guest favorite

Cottage in Cornwall

4.93 out of 5 average rating, 147 reviews

Newly Built Cottage in Housatonic Valley

This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Guest favorite

Cottage in Bethlehem

4.98 out of 5 average rating, 100 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

Home in Milford

5 out of 5 average rating, 101 reviews

Steps2Beach, Fish Pond w/Tropical Backyard Oasis!

🌴Steps from Walnut Beach & Silver Sands State Park, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Guest favorite

Cottage in Plymouth

4.94 out of 5 average rating, 113 reviews

Lakefront Cozy Oasis 2BR w/ stunning sunset views

It’s the Lakefront Paradise you’ve been searching for: Escape to Cozy Oasis where peaceful waters meet modern comfort! Wake to stunning views, spend the day kayaking around the lake, and unwind with breathtaking sunsets from your private deck. This pet-friendly retreat offers high-speed WiFi for remote work, fully equipped kitchen for home-cooked meals, and cozy entertainment spaces. Perfect for romantic getaways or family adventures - your serene lakeside escape awaits!

Guest favorite

Home in Bristol

4.92 out of 5 average rating, 171 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Guest favorite

Cottage in North East

4.87 out of 5 average rating, 151 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

Guest favorite

Cottage in Sharon

4.92 out of 5 average rating, 171 reviews

Foxfire Hill: A Bit of Luxury in the Countryside

Enjoys luxurious Get away to lovely Sharon, CT, just 2 hours from NYC/3 hours from Boston. Enjoy a chill vibe, garden and mountain views, and fresh organic eggs from our lovely flock of hens. We’ve created a luxurious and spacious modern feel, in a bucolic farmland setting. All newly refurbished with a luxurious modern bath with rain shower and fabulous marble stone work. Coyuchi bedding, soft organic cotton linens, and gourmet kitchen!

Guest favorite

Home in Stratford

4.94 out of 5 average rating, 173 reviews

Cozy Colonial - Private Hot Tub & Entire House

The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.