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Holiday rentals in Chatham

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Quick stats about holiday rentals in Chatham

  • Total holiday rentals

    Explore 10 holiday rentals in Chatham

  • Nightly prices starting at

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

  • Verified guest reviews

    Over 1,800 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Chatham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chatham rentals

  • 4.9 Average rating

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

Top-rated holiday rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cabin in Chatham

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

4.92 out of 5 average rating, 145 reviews
Top guest favourite
Home in Chatham

A unique village home steps to shops, café, nature

This spacious four-bedroom, one-and-a-half-bath listing invites you to unwind in an old home full of character and warmth, with original features and vintage décor. Well stocked eco friendly provisions and fragrance/toxin free. Two dedicated workspaces with desks provide quiet areas for focused work. 10 minute walk to Main Street Chatham via sidewalk, enjoy nearby cafés, shops, and trails. An easy drive to the Berkshires, Hudson, or Albany, this house is truly one of a kind. Check in at 2pm.

5.0 out of 5 average rating, 26 reviews
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
Superhost
An outdoor dining area is set under a large green umbrella, featuring a circular glass table surrounded by four wicker chairs. A propane barbecue grill stands nearby. Lush greenery and a wooden fence create a private atmosphere in the well-maintained gravel space.
Home in Chatham

Walk to Main Chatham Villg Fully stocked Priv Park

WELCOME ALL. Pedestrian/Bike friendly Village home 200' to Main St pubs pizza Crandall, Yianni's, Bimi's fine & fun dining. PS21/McHaydn live theaters, shopping. Town park w/swim pond, free tennis courts w/in a mile. 12mi Hudson Amtrak (taxi, Uber avail). ArtOmi, Hawthorne Valley, Tanglewood near. Keyless entry. 100% smoke/pet-free property. Check-in 4pm/-out 11am. 2 laundromats w/in 1/2 mile. High-speed wifi & parking at door. Stocked home. Private outdoor dining w/propane bbq. 2 guests max.

4.86 out of 5 average rating, 221 reviews
Guest favourite
A comfortably furnished living room features a gray sectional sofa and a wooden coffee table. A flat-screen television is positioned on a media console, complemented by two lamps on wooden side tables. Natural light filters through sheer window curtains, illuminating a colorful area rug.
Home in Chatham

Chatham Country Getaway

Highly rated, bright, open concept, two bedroom, one bath, duplex house. Conveniently located just one mile from Main St in Chatham between the Chatham Berry Farm and Mac-Haydn Theater. Just a 5 min drive from the TSP, a 10 minute drive to Art Omi, 20 min to Hudson about 35 to 40 minutes from Catamount Mountain, Bosquet, Jiminy Peak Ski Resort, Great Barrington, MA, and Tanglewood. Short term to semi long term stays are welcome and up to two pets may be allowed with prior approval from me.

4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Chatham

Private Penthouse Apt in Historic Landmark 3-BR

Enjoy the privacy of this 3 bdrm apartment with the convenience of a charming, full-service restaurant just 2 flights down. This newly renovated space is located in a private section of the historic 'Chatham House', once a resort for artists & tourists of the Catskill Mountains. While the space & ease of a cozy tavern just below may incur some lazy, make sure you take a stroll to Main St.Chatham just steps away where you can shop, eat or even take in a movie. 20 min drive to Hudson Amtrak

4.97 out of 5 average rating, 62 reviews
Guest favourite
The living room features a sectional couch in a neutral fabric, arranged invitingly around a coffee table. A flat-screen TV is positioned on a media console across from the seating area. A dining table with chairs and a hutch filled with tableware are visible in the background.
Flat in Chatham

Kinderhaus Loft in Chatham, New York

Kinderhaus Loft is on the 3rd floor accessed via an exterior stair case with a deck where you can enjoy views of the gardens & stars. There are lounge chairs and a grill for you to enjoy. The loft is in the center of the Village. You can walk to restaurants, shops, & the Crandall Theatre. You are within a mile of PS21 and MacHaydn Theater. You can also explore Hudson 12 miles away, Kinderhook 6 miles away & the Berkshires are 20-30 miles away. Close to hiking, skiing, theater & the arts.

5.0 out of 5 average rating, 45 reviews
Top guest favourite
A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.
Guest suite in Valatie

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

4.98 out of 5 average rating, 291 reviews
Top guest favourite
A spacious front porch features several wooden rocking chairs and a swing, positioned against stone columns. The floor is lined with wooden planks, and greenery is visible in the background. Sunlight filters through the trees, creating a serene outdoor seating area.
Home in Old Chatham

Monk's Bunk, Old Chatham

Forget your worries in this spacious and serene space. Tucked behind a large flowering hedge, Monk's Bunk is a rambling country home, surrounded by lawns, wildflowers and forest. Enjoy coffee on the back patio while listening to the brook and the birds. Stroll the forest path to Pinwheel Point overlook, or relax on the sunny front porch with a book. Haddock Hill Road is a cherished Dirt Road of Columbia County, and connects to the best hiking and biking in the Taconic Range

5.0 out of 5 average rating, 33 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
Top guest favourite
The exterior of the tiny house is presented, featuring a sleek, modern design with large windows allowing natural light. A spacious deck made of wooden planks leads to a seating area with a table and chairs, surrounded by open fields and trees.
Tiny home in Chatham

Peaceful Tiny House Escape by Hudson & Berkshires

Welcome to "The Tiny" at The Hemptons in the Hudson Valley. The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.

4.99 out of 5 average rating, 283 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

Popular amenities for Chatham holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Chatham

Guest favourite
A modern Nordic Cabin is nestled among tall trees, showcasing a blend of dark exterior siding and natural wood accents. Stone steps lead up to the entrance, framed by lush greenery. The setting is enhanced by a vibrant sunset sky, casting warm hues over the scene.
Home in Chatham

Nordic Cabin - Light-Filled & Spacious with Firepi

4.88 out of 5 average rating, 59 reviews
Top guest favourite
A wooden cabin nestled among green trees showcases a welcoming entrance with steps leading up to a spacious deck. Natural light fills the facade, accentuating the structure's earthy tones and inviting presence amidst the surrounding forest.
Cabin in Spencertown

Wake Up in the Woods · A Cozy Fall Escape

4.97 out of 5 average rating, 35 reviews
Top guest favourite
A serene view of expansive farmland stretches across the horizon, adorned with rolling hills and lush greenery. A wooden railing frames the scene, while a distant red barn is visible amid trees under a pastel sky at dusk.
Barn in East Chatham

The Loft @ Sweet Pea Farms

5.0 out of 5 average rating, 51 reviews
Guest favourite
A cozy living room is featured, showcasing two inviting sofas arranged around a round coffee table. Built-in shelves are adorned with decorative blue and white ceramics. A fireplace is centrally located, with light streaming in from multiple windows dressed with blue trim.
Home in Old Chatham

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

4.94 out of 5 average rating, 54 reviews
Guest favourite
Cottage in Chatham

Charming cottage w/ pool, fire pit & privacy

4.83 out of 5 average rating, 95 reviews
Top guest favourite
An aerial view captures the serene landscape surrounding the home, showcasing a mix of trees transitioning into autumn colors. The house is situated on a green patch of land, with a winding path leading towards it, surrounded by the natural beauty of the countryside.
Home in Town of Hillsdale

Gorgeous Mountain Views Retreat: Family & Nature

4.98 out of 5 average rating, 83 reviews
Top guest favourite
Farm stay in Ghent

The Farmhouse at Ten Barn Farm

4.99 out of 5 average rating, 97 reviews
Top guest favourite
The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.
Home in Old Chatham

The Red House

4.99 out of 5 average rating, 84 reviews

Frequently Asked Questions

  • What are the best places to stay in Chatham?

    Stays in Chatham range from village apartments to country homes with scenic views. Areas around the historic district and rural surroundings are frequently suggested for a peaceful experience.

  • What are the best things to do in Chatham with kids?

    Children enjoy exploring parks, visiting working farms, and attending performances or workshops at local theaters. Village playgrounds and hands-on art activities are popular family choices.

  • What are some of the best things to do in Chatham?

    Explore galleries, enjoy live theater, and sample local food at village cafes. Nearby natural areas and parks provide opportunities for walks, picnics, and outdoor activities throughout the year.

  • How is the weather in Chatham?

    Chatham has cold winters ranging from 16–33°F (-9–1°C) with some snowfall, and warm summers near 62–84°F (17–29°C) with frequent rain showers. Spring and autumn bring mild temperatures and colorful scenery.

  • When is the best time to visit Chatham?

    Late spring through early autumn is often recommended, with mild temperatures and seasonal events. Fall colors and local festivals give the village extra charm, while winter appeals to those seeking a quiet, cozy retreat.

  • What are the best places to visit in Chatham?

    Chatham has local art galleries, indie shops, and theaters known for plays and music. You can explore the village's cafes and stroll nature preserves around the area for a blend of culture and outdoor experiences.

  • What are some hiking trails in Chatham?

    Chatham has walking paths through its village and in nearby natural areas, with trails winding through forests and fields. Seasonal wildflower hikes and gentle routes along local preserves are frequently suggested.

  • What are some family activities we can do in Chatham?

    Families explore parks, visit farm stands, and enjoy performances at local theaters. Hands-on workshops, public playgrounds, and seasonal festivals bring opportunities for all ages.

  • What are some of the best day trip ideas from Chatham?

    Explore neighboring small towns with historic architecture, local markets, and antique shops. The region has scenic areas for hiking, nature reserves, and art galleries that invite discovery.

  • Are there any pet friendly accommodations available in Chatham?

    Chatham has several vacation rentals and stays that welcome pets. Many properties around the village and surrounding countryside are pet-friendly, making it easy to travel with your companion.

  • What are some local tips for visiting Chatham?

    Early mornings are quieter for exploring village shops, and weekends often fill with farmers markets or pop-up events. Locals suggest checking community notice boards for workshops or performances.

  • What is Chatham known for?

    Chatham is known for its vibrant arts scene, historic architecture, and welcoming atmosphere. The village hosts theater performances, artisan shops, and community events rooted in local traditions.

  • What are the best hidden gems to explore in Chatham?

    Discover locally owned bookshops, small-batch bakeries, and tucked-away art studios around the village. Many visitors seek out quiet nature preserves, historic libraries, and community gardens off the main streets.

  • What are the best foods to try in Chatham?

    Locally grown produce, farm-fresh cheeses, and baked goods are often recommended. The village has independent cafes, restaurants with seasonal menus, and markets featuring regional specialties.

  • What should I bring for a trip to Chatham?

    Pack layers for shifting weather, with warmer clothing for winter and lighter options in summer. Rain jackets are useful year-round, and comfortable shoes make exploring local shops and trails easier.

  • What is the nightlife in Chatham like?

    Chatham’s nightlife has cozy venues for live music, casual dining, and occasional arts performances. Evenings in the village often feature relaxed atmospheres and social gatherings linked to arts and culture.

  • What are the most popular events or festivals in Chatham?

    Community festivals, farmers markets, and arts events are often recommended, especially during late spring and autumn. The Chatham Film Festival draws visitors for independent screenings, while local harvest celebrations mark the season.

  • Are there family friendly vacation rentals in Chatham?

    Chatham has a variety of family-friendly vacation rentals, including larger homes and apartments in the village and countryside. Many properties offer amenities such as outdoor space, kitchens, and areas for kids to play.

Destinations to explore