Vacation rentals in Old Chatham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Old Chatham

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

0 of 0 items showing

1 of 3 pages

Superhost

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 184 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Superhost

The chalet is set among trees, featuring a wooden exterior and a spacious deck adorned with warm lights. The two-story structure includes a balcony on the upper level and large windows inviting natural light. A garage is visible to the right, situated on a green lawn.

Cabin in Ghent

4.99 out of 5 average rating, 268 reviews

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom (5-beds), 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features an open floor plan, luxury bathrooms, new, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. The home is surrounded by nature—trees, trails, streams, and farms—all close by. Hike, bike, kayak, or go to a brewery. Discover the nearby Hudson Valley farms, ski in the Berkshires, or visit the trendy town of Hudson, NY.

Superhost

A winding pathway of rectangular stepping stones leads through a lush green lawn. Flower beds with colorful blooms border the path, complemented by a bird feeder and decorative fencing nearby. Towering trees provide a natural backdrop, enhancing the serene outdoor setting.

Cottage in Old Chatham

4.89 out of 5 average rating, 9 reviews

Cozy Cottage Retreat

This is an idyllic private one-bedroom cottage nestled in the woods on a dirt road. Equipped with a private queen-sized bedroom; there is also a full-sized pull-out couch in the living room. A fully equipped kitchen, dining area, bathroom with a tub & shower. Perfect for hikers, hunters, fly fishers, or just relax and unwind. Easy access to Columbia , Greene, Albany & Berkshire Ctys; Hancock Shaker Village, Tanglewood, MA, or Ski Resorts. The hosts live in the main house. No Smoking. No pets.

Superhost

A serene swimming hole is surrounded by lush greenery and rocky terrain. Calm waters reflect the foliage; a child is perched on a large stone at the water's edge, enjoying the natural setting. The area invites guests for outdoor relaxation and exploration.

Cottage in Chatham Center

4.89 out of 5 average rating, 158 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)!

Superhost

Cottage in New Lebanon

4.95 out of 5 average rating, 191 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 table.

Superhost

A wooden porch features structural beams and railings, providing a welcoming entrance to the house. Surrounding greenery includes trees and low-growing plants, creating a natural and shaded ambiance. The exterior is painted in a dark tone, complemented by red doors, enhancing the structure's character.

Home in Chatham

4.89 out of 5 average rating, 171 reviews

Country house on Indian Creek

Tucked away in a beautiful valley, this house is surrounded by farm hills and creeks. Located on 5 acres of grassland and 10 acres of woodland. Close to 3 ski mountains, 2 lakes, and tons of hiking and mountain biking trails. Very peaceful and spacious place to unwind. Just 5 minutes away from town center but feels miles away from everything. If you open my profile picture you will find my guidebook, which gives you a idea of some places to eat and attractions around the area.

Superhost

A front porch is adorned with a single plastic chair resting on wooden decking. Surrounding greenery includes a flowering hedge, providing a natural border. A gravel pathway is visible beyond the porch, leading to a grassy area shaded by trees.

Home in Old Chatham

5 out of 5 average rating, 19 reviews

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

Superhost

A sunlit hallway features a long wooden shelf, lined with an assortment of books. Two windows provide natural light, revealing views of the surrounding greenery. The space opens into the kitchen and dining area, showcasing a blend of rustic and modern design elements.

Home in Old Chatham

4.98 out of 5 average rating, 48 reviews

The Red House

Welcome to our historic and charming home, tucked away on 50 acres of beautiful, serene woodland. Built in 1840, our 2200 square foot residence combines the authenticity of centuries-old wood beams with cozy, comfortable interiors. The Red House is close to the charming towns of the Hudson Valley: Chatham, Kinderhook, Ghent and Hudson. There is also easy access to Tanglewood, Jacob's Pillow, Mass MOCA, Williamstown and Tannery Pond.

Superhost

A small table with a bronze metal base and a wooden top is set beside a gently flowing stream. A wrought iron chair accompanies the table, surrounded by lush greenery. The area features a peaceful woodland backdrop, enhancing the sense of nature.

Home in Chatham

4.9 out of 5 average rating, 237 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.

Superhost

A modern kitchen with green cabinetry showcases a floral backsplash. A farmhouse sink rests under a window. Various kitchen appliances, including a coffee maker, are arranged neatly. The open layout leads to a living area featuring a wood stove and exposed beams.

Cabin in East Nassau

4.99 out of 5 average rating, 104 reviews

Artistic Blue Cabin with private creek and forest

Our wood cabin is located in a secluded area on 5 acres of forest and a creek flowing through the property that you see from every room. Newly renovated, our cabin is finished with refined colonial details and decorated with furniture from all over the world. Enjoy a morning coffee with a view of the creek by the wood burning stove or take a hike through our 5 acres of backyard forest. This property is the perfect escape.

Superhost

Three decorative ceramic figures are positioned on a countertop, their colorful designs creating a cheerful focal point. Two white mugs are visible nearby, alongside a white utensil holder that contains various kitchen tools. Natural light filters through a window, enhancing the vibrant hues of the figures.

Tiny home in Chatham

4.99 out of 5 average rating, 414 reviews

Sugar Shack | Romantic Tiny Home + Hot Tub

Sugar Shack | Romantic Tiny Home + Hot Tub. Escape to this 300 sq ft tiny home with private hot tub and she-shed. A peaceful, romantic getaway in the heart of Chatham—just steps from shops, dining, and theater. Only 2.5 hrs from NYC & Boston. Hike, explore, soak under the stars, or cozy up by the firepit. Thoughtfully designed for privacy, comfort, and indulgence. A blissful upstate NY retreat at @artparkhomes.

Superhost

A white chicken stands near a basket of eggs, surrounded by daffodils. The setting includes a background of a variety of chickens and natural greenery, highlighting the farm's vibrant agricultural life.

Loft in East Nassau

4.99 out of 5 average rating, 181 reviews

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Old Chatham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Old Chatham

Guest favorite

A patio area features a stone fire ring surrounded by wooden Adirondack chairs. A red umbrella shades a dining table nearby, with additional seating areas visible. Lush green trees and shrubs provide a natural setting beside the barn's vibrant exterior.

Farm stay in New Lebanon

4.95 out of 5 average rating, 225 reviews

Barn Stay at Shadowbrook Farm

JenniferRating, 5 stars1 month ago

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

Top guest favorite

A wooden deck is surrounded by lush greenery, overlooking a serene natural landscape. Outdoor seating is provided, featuring a coffee table and comfortable chairs. A grill is visible nearby, situated against a backdrop of trees and hills, creating a peaceful retreat.

Home in Canaan

4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

Superhost

A view of an open living space features a black fireplace and a round dining table. Light wood flooring extends towards a hallway that leads to various rooms. A colorful wall art piece adds a pop of interest, while a plant on the table introduces a touch of greenery.

Home in Chatham

5 out of 5 average rating, 3 reviews

Chatham Farmhouse Hudson Valley

NazariyRating, 5 stars4 months ago

We had an amazing weekend stay at Micah’s place! The home was absolutely stunning—super clean, beautifully furnished, and stocked with everything you could possibly need. The kitchen was fully equipped with all the appliances, making it easy to cook and enjoy meals. The highlight was the TV room, which had incredible sound quality and made for a perfect spot to relax. The home was also very child-friendly, which made our stay even more enjoyable. Overall, a fantastic experience! Highly recommend this place.

Top guest favorite

Home in Canaan

5 out of 5 average rating, 65 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

MichelleRating, 5 stars6 days ago

We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

Top guest favorite

The exterior of the A-Frame Log Cabin displays a dark wooden facade, accented by multiple balconies. Warm lights illuminate the windows, hinting at the cozy interior. The cabin is surrounded by trees, and a gravel parking area is visible in the foreground.

Cabin in Hannacroix

4.99 out of 5 average rating, 67 reviews

A-Frame Log Cabin: Hot tub, views, & EV2 charger!

MinetteRating, 5 stars6 days ago

Really enjoyed our stay! Was perfect for our family to stay all in one place. Darin responded in a timely manner and was very helpful. Pool table was a great addition! Loved the location, it was beautiful & peaceful. We were disappointed we didn't see any bears :0) LOL

Guest favorite

A serene view of a creek surrounded by trees displaying autumn foliage. The water reflects the colorful leaves and the clear sky, creating a tranquil atmosphere. Rocks line the creek's edge, offering a natural contrast to the vibrant scenery.

Cottage in Malden Bridge

4.96 out of 5 average rating, 23 reviews

Cozy, charming cottage by the creek w/2 queen beds

BonnieRating, 5 stars12 months ago

Martha was a great host! The cabin was perfect and exactly as described. The fenced in yard was perfect for our pup! She took time to make a list of local things to do. I hope to come back and stay here again soon!

Top guest favorite

A spacious living area features a creamy sectional sofa paired with a minimalist round coffee table. Natural light streams through large windows, casting soft shadows on the light wooden floor. A cozy armchair is complemented by decorative accents, enhancing a calm and inviting vibe.

Cabin in Saugerties

5 out of 5 average rating, 35 reviews

Luxury A-Frame Cabin w/ Hot Tub

ChrisRating, 5 stars4 days ago

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

Guest favorite

A bright living space features large floor-to-ceiling windows that allow natural light to fill the room. A cozy seating arrangement includes modern chairs and a round coffee table on a patterned rug, with a view of the trees and lake visible through the glass.

Home in Valatie

4.97 out of 5 average rating, 32 reviews

Majestic lake front house

PeterRating, 5 stars1 month ago

We had a great time at Francois & Ann's oasis by the lake. It was so relaxing to wake up, look at the lake, and listen to birds chirp. If you are looking for isolation, this place does the trick, We didn't see anyone all week on the lake or at the other cabins until the day we left. The lake has excellent fishing. With little effort, we caught several decent-sized bass and pickerel right off the dock. The location is ideal. You feel like you are out in the country, but are close to great restaurants in Kinderhook and only 25 minutes from Hudson or Albany. It's also only an hour from Mass Moca and 90 minutes to Cooperstown. Francois and Ann were very communicative and quickly responded to questions and comments.

Show all

Vacation rentals in Old Chatham

Top-rated vacation rentals in Old Chatham

Vacation rentals for every style

Popular amenities for Old Chatham vacation rentals

Other great vacation rentals in Old Chatham

Destinations to explore