Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

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Top guest favorite

The charming farmhouse stands amid lush greenery, framed by mature trees. A wraparound porch invites relaxation, while well-maintained grass leads to the entrance. Large windows allow natural light to fill the interior, enhancing the welcoming atmosphere of the property.

Home in Ghent

4.98 out of 5 average rating, 131 reviews

Stylish Hawthorne Valley Farmhouse Retreat

Hawthorne is a renovated 1920s farmhouse set on 11 acres of pastoral fields, forest and pond, featuring stylish, comfortable, art-filled white and green rooms. Take in the view from the sun porch, nap on the big L-shaped sofa, share cocktails in the field overlooking the valley, and cozy up by the fieldstone fireplace at night. A fully equipped house, with Watson Kennedy goods throughout. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, with Malin+Goetz & Molton Brown supplies make this your luxe country getaway. Now with unlimited WiFi. The perfect getaway for one to three couples, Hawthorne offers multiple rooms and lots of space for maximum relaxation and taking in the country. >> Enjoy the view from the sun-drenched front porch. >> Nap on the big L-shaped sofa in the living room. The two extra deep Restoration Hardware couches are 7’ long; they also serve as larger than usual single beds >> Cozy up with a book by the fieldstone fireplace in the fully screened back porch (with glass panels in Fall and Winter). >> Share sunset cocktails in the Adirondack chairs up in the field overlooking the valley. >> Cook in the well-equipped kitchen. >> Eat your candle-lit dinner in the dining room overlooking the valley. This is a fully equipped country farmhouse, with Watson Kennedy goods throughout the home. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, and Malin+Goetz bath supplies make this your luxe country getaway. You will be the only guests in the house, with no one else on-site. Lots of hiking in the valley and nearby conservancy areas, biking on country roads, cross-country, downhill or snowshoe during the snowy months, or take in all the antique shops and history year-round. This peaceful property is minutes from the Hawthorne Valley Farm store, 20 minutes to the world-class food and vintage mecca of Hudson, and 30 minutes from the culture and history of Tanglewood, Jacobs PIllow and the Berkshires. For recreation there is hiking in the valley and nearby conservancy areas, biking on country roads, or cross-country, downhill or snowshoeing during the snowy months. Hawthorne is a 2-hour drive from NYC or a 2-hour Amtrak ride from Penn Station to Hudson, and then a 20 minute drive by car or taxi. The house is conveniently close to the Taconic Parkway, while set in a peaceful and quiet valley.

Guest favorite

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

4.89 out of 5 average rating, 193 reviews

Chatham Villg Walk to Main. 100% Smoke/Animal Free

WELCOME ALL. Pedestrian/Bike friendly Village home 200' to Main St pubs/pizza/Crandall/Yianni's/Bimi's fine & fun dining. PS21/McHaydn live theatrs, shopping, town park w/swim pond/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. Free high-speed WiFi & parking at door. Fully stocked home. Private outdoor dining w/propane bbq. 2 guests max. Look forward to your stay! 😊

Superhost

An airy interior showcases exposed wooden beams and a blend of modern and rustic decor. A kitchen counter with stools is positioned towards the left, complemented by a dining table with chairs in the center. A cozy bedroom is visible through the doorway on the right.

Apartment in Philmont

4.9 out of 5 average rating, 120 reviews

Beautiful space in the heart of Philmont

Enjoy the elegant ambience of this airy and bespoke space, just two doors up from the excellent restaurant Local 111, as well as the Co-op, where you can pick up delicious local produce, meats, and baked goods. A couple blocks from the Philmont Pub, another fantastic place to eat and enjoy the evenings. Minutes from Hudson, this town is literally in the center of Columbia County. A short drive to Catamount, Bash Bish, the Hudson River, the Catskills, the Berkshires, no end of places to explore!

Top guest favorite

The charming cottage is set within a lush garden, featuring a gently curved stone pathway leading to the front door. Surrounding greenery includes well-maintained shrubs and trees, creating a tranquil and inviting outdoor setting.

Cottage in Kinderhook

4.98 out of 5 average rating, 226 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Guest favorite

A wooden rocking chair sits on a quaint porch, next to vibrant flower pots filled with blooming plants. Green grasses and a hint of autumn foliage create a serene outdoor setting, inviting relaxation and peaceful moments.

Cottage in New Lebanon

4.95 out of 5 average rating, 197 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

Guest favorite

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

4.9 out of 5 average rating, 162 reviews

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)!

Guest favorite

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

4.95 out of 5 average rating, 108 reviews

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.

Superhost

A modern tiny house is surrounded by the serene landscape of Columbia County. Bare trees and evergreen shrubs frame the structure, while the soft grass adds a natural touch. Large windows allow natural light to illuminate the interior, enhancing the connection to the outdoors.

Tiny home in Ghent

4.96 out of 5 average rating, 159 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

Tiny house on 30 private acres with a mile of walkable trails in beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in-ground pool and barn pool house. Enjoy the 4 person sauna year round. ** Pool closed mid-October - mid-May. Confirm before booking. Under 18 guests not permitted.

Top guest favorite

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

4.99 out of 5 average rating, 255 reviews

Tiny House, Big Adventure on 70 acres

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.

Guest favorite

The exterior of the house displays a light-colored façade with multiple windows allowing natural light to illuminate the space. A front porch area with steps leads to the entrance, and surrounding greenery adds a touch of nature to the setting.

Home in Chatham

4.9 out of 5 average rating, 251 reviews

Pet-friendly. Private. Host leans left. 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.

Guest favorite

A bright bedroom features a spacious bed with neutral bedding, framed by wooden walls and beams. Natural light fills the room through a large window, showcasing a glimpse of the outdoor area. A small side table and a decorative plant complement the simple, serene design.

Cabin in Chatham

4.97 out of 5 average rating, 139 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Guest favorite

An open kitchen and dining area feature rustic wooden beams and warm wooden floors. A round dining table with black chairs is positioned near double glass doors leading to a deck. An island with stools offers additional seating, with kitchen amenities visible in the background.

Home in Ghent

4.95 out of 5 average rating, 253 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!