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Pet-friendly holiday rentals in Chatham

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

  • Nightly prices starting at

    Chatham holiday rentals start at €26 per night before taxes and fees

  • Verified guest reviews

    Over 1,050 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chatham rentals

  • 5 Average rating

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

Top-rated pet-friendly home rentals in Chatham

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

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Top guest favourite
Tiny home in Chatham

Romantic-Private-Western Tiny Cabin w/HOT TUB

Sept. SPECIAL (Mon-Thurs): Prosecco/s’mores kit/firepit supplies. Just 2.5 hours from NYC, escape to The Hitching Post—a romantic Western-inspired tiny home in Chatham, NY w/private hot tub, firepit, outdoor shower & rustic luxury throughout. Once the hideout of a legendary samurai cowboy, this unique retreat features a cozy queen bed nook, luxe bath & kitchenette. Just a 2-minute walk to Chatham’s restaurants, shops, brewery & theater. A perfect Hudson Valley getaway for couples. @artparkhomes

5.0 out of 5 average rating, 104 reviews
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!

4.97 out of 5 average rating, 107 reviews
Guest favourite
A spacious living area features a large, orange sectional sofa adorned with various throw pillows. A massive stone fireplace is positioned against one wall, with a flat-screen television mounted nearby. Natural light is welcomed through windows, complementing the rustic stone and wood ceiling.
Cottage in Chatham Center

Kinderhook Creek Private Retreat

Charming home at the end of a country road on the Kinderhook Creek surrounded by fields and woods with hiking/biking trails and a very private swimming hole! HVAC and a cozy fireplace make this a comfortable year-round getaway and a wonderful place to enjoy the fall colors! Within easy drive of endless things to do and places to explore such as the quaint town of Chatham (5 min), Tanglewood (35 min), antiquing in Hudson (20 min) and good skiing too (Catamount 30 min, Butternut 45 min)!

4.87 out of 5 average rating, 182 reviews
Guest favourite
A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.
Cabin in Town of Hillsdale

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

4.91 out of 5 average rating, 128 reviews
Top guest favourite
A charming colonial home is depicted, featuring white siding and a green front door. Potted flowers decorate the entryway, and several windows provide natural light. The well-maintained lawn is surrounded by colorful blooms, contributing to the home's inviting curb appeal.
Home in Kinderhook

Modern and cozy 3 bedroom with outdoor oasis

Kick back and relax in this serene, stylish, and totally updated colonial home in Upstate New York. Enjoy views of a beautiful apple orchard and the Catskill Mountains, while relaxing in the back yard oasis, with a hot tub, dining area, gas fire pit, and gas grill. Located walking distance from local restaurants in the Village of Kinderhook and attractions, including the Samascott Orchard and Samascott's Garden Market. Drive 20 minutes to Hudson and 30 minutes to Albany.

4.95 out of 5 average rating, 125 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

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

4.98 out of 5 average rating, 134 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 Retreat Near Hudson & the Berkshires

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. A private outdoor sauna will be ready for all stays beginning October 1, 2026. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

4.96 out of 5 average rating, 112 reviews
Guest favourite
Home in Chatham

Chatham on the Creek. Pet friendly. F Trump

This is a recently renovated 120-year-old house. There are no neighbors in sight. The backyard is a wooded area. There is a stream, fire pit, table, and chairs. The garage has been converted into a game room with ping pong, pool, couches and a bar. Across the road is farmland. It's less than one mile off the Taconic State Parkway exit, and about a half hour to both Catamount and Jimminy Peak (ski resorts). Twenty minutes from Hudson.

4.91 out of 5 average rating, 295 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!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

4.83 out of 5 average rating, 304 reviews
Guest favourite
Cottage in Craryville

Farm Cottage w/ Donkeys, Fire Pit & Wood Stove

Welcome to The Cottage at Raspberry Ridge, a charming Hudson Valley farm stay surrounded by gardens, woodlands, donkeys, and chickens. This cozy 3-bedroom retreat blends rustic character with modern comfort, offering a wood-burning stove, peaceful outdoor spaces, and access to the farm grounds. Just minutes from Hudson, Great Barrington, hiking trails, and local farms, it's the perfect place to slow down and reconnect.

4.91 out of 5 average rating, 599 reviews
Superhost
Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

4.91 out of 5 average rating, 149 reviews
Guest favourite
An outdoor area is illuminated by warm lights, featuring a hot tub nestled beneath a canopy. Comfortable seating is arranged nearby, surrounded by lush greenery. A wooden deck provides a relaxing space, with a partially enclosed yard that enhances privacy.
Home in Hudson

Vibing Hot Tub Cottage | Pet-Friendly | Hudson, NY

Step into The Vine — a sun-warmed, pet-friendly vineyard-inspired boho cottage in Hudson Valley, NY. Warm wood, cork accents, a wine bar, and a neon "Vibing in the Vine" sign set the mood. Your private hot tub and backyard fire await. Guests call it an incredible escape from the city — bigger, cozier, and better stocked than expected. Minutes from downtown Hudson, wineries, and trails.

4.95 out of 5 average rating, 170 reviews

Popular amenities for Chatham pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
The exterior of a single-story home is showcased, featuring a classic mid-century modern design. A spacious screened-in porch and well-maintained grounds overlook the serene river. The backdrop includes rolling hills and a cloudy sky, hinting at the scenic beauty of the surrounding landscape.
Home in Hudson

Owl's Nest (Rip's Retreat)

4.87 out of 5 average rating, 118 reviews
Superhost
Home in Hudson

19th Century Mill House with River View

4.85 out of 5 average rating, 152 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

4.98 out of 5 average rating, 108 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

4.97 out of 5 average rating, 231 reviews
Guest favourite
A cozy living area features a leather sectional sofa alongside a plush, oversized armchair. A low coffee table is positioned on a patterned area rug. Light streams through large windows adorned with sheer curtains, creating a warm and inviting atmosphere in the space.
Home in Hudson

Spacious 2BR Flat in the Heart of Hudson

4.95 out of 5 average rating, 222 reviews
Top guest favourite
A serene landscape is captured, featuring a tall tree with budding leaves beside a rustic barn. Mist gently envelops the grassy area, creating a tranquil atmosphere as light filters through the trees in the background.
Home in Saugerties

The Stone House

4.98 out of 5 average rating, 195 reviews
Top guest favourite
The open-concept dining area features a wooden table surrounded by white chairs, set against large windows that allow natural light. A modern kitchen with a central island, stylish pendant lights, and access to a staircase is visible, creating a seamless flow throughout the space.
Home in Albany

Modern Cottage-Perfect for Families!

4.96 out of 5 average rating, 176 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!

4.95 out of 5 average rating, 188 reviews

Pet-friendly home rentals with a pool

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.

4.96 out of 5 average rating, 150 reviews
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

4.95 out of 5 average rating, 170 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.

5.0 out of 5 average rating, 111 reviews
Top guest favourite
A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.
Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

4.98 out of 5 average rating, 108 reviews
Top guest favourite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens

Private lakefront home, hot tub & resort amenities

4.95 out of 5 average rating, 192 reviews
Superhost
An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.
Holiday home in Athens

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

4.86 out of 5 average rating, 128 reviews
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

4.88 out of 5 average rating, 220 reviews
Guest favourite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

4.94 out of 5 average rating, 398 reviews

Private, pet-friendly home rentals

Guest favourite
A spacious bedroom is bathed in natural light from large windows, showcasing a cozy queen-size bed with crisp linens. An inviting red chair and a small side table create a nook for relaxation, while a vintage lamp adds warmth to the serene atmosphere.
Flat in Hudson

Chic Parisian Apartment on Warren St | Hudson

4.93 out of 5 average rating, 434 reviews
Top guest favourite
An aerial view captures the serene landscape surrounding the red barn, nestled among lush green fields. Pastures and trees create a tranquil setting, with distant farmland visible in the background, providing a sense of seclusion in the countryside.
Farm stay in Kinderhook

Barn House: open layout isolated farm Hudson area

4.87 out of 5 average rating, 272 reviews
Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top

Contemporary Cabin in Catskill Mountains

4.99 out of 5 average rating, 179 reviews
Guest favourite
A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.
Guest house in Great Barrington

Sweet Victorian in Housatonic

4.95 out of 5 average rating, 174 reviews
Guest favourite
A modern kitchen features rich blue cabinetry paired with a white countertop. A double sink and stainless steel appliances create a functional space. A window allows natural light to brighten the area, while a patterned rug adds warmth to the wooden flooring.
Flat in Valatie

Apartment w/Hudson-Electric Trail Access

4.96 out of 5 average rating, 101 reviews
Guest favourite
A well-lit studio space features a spacious bed dressed in white linens with decorative pillows. Light wooden cabinets and a dining table with four chairs are visible in the background, complemented by a full kitchen equipped with essential appliances.
Guest suite in Hudson

Harmony Valley Home, bright & inviting studio

4.94 out of 5 average rating, 231 reviews
Top guest favourite
The kitchen features deep black cabinetry paired with warm wood countertops. A window above the sink allows natural light to illuminate the floral wallpaper. Modern fixtures and a stylish faucet enhance the space, offering a functional area for meal preparation.
Cabin in Hudson

Cozy Grove Luxury Cabin

4.96 out of 5 average rating, 124 reviews
Top guest favourite
An open living area showcases exposed brick walls and wooden flooring, complemented by large windows allowing natural light. Two turquoise couches are positioned on a light area rug, facing a modern fireplace. A spiral staircase leads to the upper level, enhancing the space's architectural interest.
Loft in Hudson

Spacious Loft on Warren Street

5.0 out of 5 average rating, 264 reviews

Destinations to explore