Airbnb your place

Pet-friendly holiday rentals in Richmond

Find and book unique pet-friendly homes on Airbnb

Quick stats about holiday rentals that are pet-friendly in Richmond

  • Total holiday rentals

    Explore 20 holiday rentals in Richmond

  • Nightly prices starting at

    Richmond holiday rentals start at $128 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Richmond holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Richmond rentals

  • 4.9 Average rating

    Richmond stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated pet-friendly home rentals in Richmond

Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

PetsOutdoor spacesBack garden

4.97 out of 5 average rating, 109 reviews
Top guest favourite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

WalkabilityOutdoor spacesTV

4.95 out of 5 average rating, 320 reviews
Guest favourite
An open kitchen and dining area feature a wooden dining table surrounded by black chairs. The space is illuminated by natural light from large windows, with a breakfast bar visible in the background. A neutral color palette adds warmth to the inviting layout.
Home in Pittsfield

Net Zero home with rustic Berkshire charm

Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Outdoor spacesWalkabilityLaundry

4.93 out of 5 average rating, 136 reviews
Guest favourite
An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.
Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Outdoor spacesWalkabilityHospitality

4.95 out of 5 average rating, 191 reviews
Guest favourite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

PetsOutdoor spacesDecor

4.96 out of 5 average rating, 114 reviews
Top guest favourite
An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.
Home in Dalton

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Outdoor spacesPetsQuiet

4.93 out of 5 average rating, 212 reviews
Guest favourite
A modern living area features large windows allowing natural light to fill the space. A cozy sofa and a comfortable chair invite relaxation, while a country-style table accommodates dining or work. The decor is enhanced by a colorful area rug and minimalistic furnishings.
Guest suite in Richmond

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

WalkabilityOutdoor spacesValue

4.94 out of 5 average rating, 207 reviews
Guest favourite
A serene view of a winding driveway surrounded by vibrant perennial gardens. Colorful flowers grow abundantly along the path, leading to a scenic landscape of rolling hills and distant mountains under a partly cloudy sky.
Home in Pittsfield

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

WalkabilityOutdoor spacesCleanliness

4.97 out of 5 average rating, 157 reviews
Guest favourite
The bedroom features a spacious bed with a light grey coverlet, accentuated by decorative pillows. Natural light filters through two windows adorned with bamboo shades. A light-colored dresser and a cozy armchair add functionality, complemented by a soft area rug on the hardwood floor.
Flat in Lenox

Lovely Downtown Lenox apt, walk to everything!

Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

PetsOutdoor spacesComfort

4.95 out of 5 average rating, 154 reviews
Top guest favourite
A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.
Home in Lee

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

Outdoor spacesPetsQuiet

4.97 out of 5 average rating, 143 reviews
Superhost
A two-story duplex is surrounded by greenery, showcasing a wooden deck with latticework. The exterior is clad in light-colored siding, with green shutters adorning the windows. A landscaped yard features various plants, and a road is visible in the background.
Serviced apartment in Canaan

Comfy - Country Family Home- Affordable

Book now!! The fall is approaching. Come enjoy the easy restful place in the Berkshires, Columbia County. We are close to apple picking and hiking, or enjoying the turning of the leaves. Quaint one bedroom duplex in the center of our little town. Shop and dine in Chatham, Lenox, Stockbridge, Great Barrington, Woodstock, Saratoga, or grill on the deck.

Outdoor spacesPetsComfort

4.84 out of 5 average rating, 117 reviews
Guest favourite
A two-story lodge is nestled among tall trees, with a babbling brook flowing in the foreground. The exterior is a rich brown wood, complemented by green foliage and rocks near the water. A small balcony is visible on the second floor, enhancing the picturesque setting.
Cottage in Austerlitz

Harvey Mountain Lodge by State Forest

Charming, fully equipped 2 1/2 bed/3 bath lodge at the end of a dirt road next to a babbling brook surrounded by 3000 acres of forest. Spend time enjoying the outdoors skiing, hiking, mountain biking, fishing, and creek walking. or exploring the Hudson Valley and the Berkshires. This is the perfect place to unplug and recharge!

PetsOutdoor spacesLong stay

4.93 out of 5 average rating, 129 reviews

Popular amenities for Richmond pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Guest favourite
The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.
Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Outdoor spacesPetsKitchen

4.93 out of 5 average rating, 109 reviews
Top guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket

Cozy lakehouse

PetsOutdoor spacesGrill

5.0 out of 5 average rating, 119 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

WalkabilityPetsGetting around

4.89 out of 5 average rating, 152 reviews
Guest favourite
A single-story wooden lodge with a green metal roof is set amidst a grassy area. The exterior is lined with windows, allowing natural light to fill the interior. Surrounding trees provide a backdrop, and a paved driveway leads to the entrance, enhancing accessibility.
Home in Pittsfield

Dancing Horse Lodge

Outdoor spacesPetsCheckout

4.87 out of 5 average rating, 331 reviews
Guest favourite
Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Outdoor spacesPetsGrill

4.94 out of 5 average rating, 135 reviews
Top guest favourite
A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.
Home in Catskill

Cheerful Catskill Village Cottage

WalkabilityOutdoor spacesLocation

4.97 out of 5 average rating, 235 reviews
Guest favourite
A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.
Home in Hudson

Bright, Airy Home in Hudson w/ TONS of Character!

PetsWalkabilityValue

4.83 out of 5 average rating, 308 reviews
Guest favourite
A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.
Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

PetsOutdoor spacesAmenities

4.88 out of 5 average rating, 108 reviews

Pet-friendly home rentals with a pool

Top guest favourite
A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.
Cottage in Averill Park

Cozy cottage with pool, walking distance to lake

PetsWalkabilityCheckout

4.95 out of 5 average rating, 171 reviews
Top guest favourite
Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

PetsWalkabilityCheck-in

4.97 out of 5 average rating, 185 reviews
Top guest favourite
The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.
Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

Outdoor spacesPetsLayout

4.98 out of 5 average rating, 135 reviews
Guest favourite
A snow-covered entrance showcases a wooden sign featuring 'SMITH UNITS 1061 - 1064.' The residential building, adorned with white siding, includes a window unit air conditioner protruding from the wall. Surrounding shrubs are blanketed with fresh snow.
Townhouse in Hancock

Beautiful Jiminy Peak Townhome Family Friendly

Outdoor spacesPetsTV

4.83 out of 5 average rating, 109 reviews
Top guest favourite
A spacious white cottage is set against a vibrant green lawn, framed by blooming white flowers. Expansive trees surround the property, overlooking rolling hills that stretch towards a tranquil river in the distance under a clear blue sky.
Home in Coxsackie

Hudson River estate guest cottage

Outdoor spacesPetsLayout

4.98 out of 5 average rating, 109 reviews
Superhost
Home in Becket

Berkshires Lodge | Pool, Hot Tub & Fire Pit

Outdoor spacesWalkabilityAmenities

4.86 out of 5 average rating, 118 reviews
Guest favourite
A cozy living area features a dark sofa with decorative pillows, complemented by a yellow armchair. A wooden coffee table sits in the center, holding books, with a rug beneath. Natural light enters through two windows, illuminating the warm wooden walls.
Tiny home in Ghent

Country Getaway Tiny House in Woods w/Pool/Sauna.

PetsWalkabilityPool

4.96 out of 5 average rating, 151 reviews
Top guest favourite
A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.
Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

WalkabilityOutdoor spacesAccess

5.0 out of 5 average rating, 114 reviews

Private, pet-friendly home rentals

Top guest favourite
Tiny home in Chatham

Romantic-Private-Western Tiny Cabin w/HOT TUB

Outdoor spacesWalkabilityCheck-in

5.0 out of 5 average rating, 105 reviews
Guest favourite
A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.
Guest house in Stockbridge

Modern barn in the heart of the Berkshires

PetsOutdoor spacesCleanliness

4.91 out of 5 average rating, 175 reviews
Guest favourite
Tiny home in New Marlborough

Bedroom Forest View I Sauna I Fire-pit I Trails

PetsOutdoor spacesAir conditioning

4.94 out of 5 average rating, 201 reviews
Guest favourite
Guest house in Great Barrington

Sweet Victorian in Housatonic

WalkabilityPetsFamily

4.95 out of 5 average rating, 177 reviews
Top guest favourite
Guest house in North Adams

Netherwood - North Adams Guest House with Views

WalkabilityPetsShared spaces

5.0 out of 5 average rating, 337 reviews
Guest favourite
Home in Richmond

Classic New England Home with direct trail access

Outdoor spacesLayoutCondition

4.95 out of 5 average rating, 21 reviews
Guest favourite
A cozy living room features a stone fireplace as the focal point, surrounded by two blue couches and an orange couch. Light streams in through two windows, enhancing the room's natural warmth. A decorative area rug adds a touch of color to the space.
Home in Pittsfield

Summer on the Lake - Berkshires near Tanglewood

WalkabilityOutdoor spacesCleanliness

4.96 out of 5 average rating, 77 reviews
Superhost
The cabin is nestled in a wooded area, surrounded by lush greenery. A large deck extends from the front of the home, with firewood stacked neatly beside it. The architecture features an A-frame design, blending harmoniously with the natural landscape.
Chalet in Lenox

Modern Chalet Near Tanglewood & Downtown Lenox

WalkabilityPetsKitchen

4.87 out of 5 average rating, 46 reviews

When is the best time to visit Richmond?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$424 SGD$439 SGD$338 SGD$339 SGD$343 SGD$426 SGD$581 SGD$484 SGD$459 SGD$424 SGD$385 SGD$448 SGD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Destinations to explore