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Chatham Vacation Rentals

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  • Upfront pricing

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chatham vacation rentals

Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
$310 nightly
The price is $350
Aug 3 - Aug 4
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
$299 nightly
The price is $337
Aug 19 - Aug 20
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
$339 nightly
The price is $380
Aug 2 - Aug 3
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$584 nightly
The price is $654
Aug 25 - Aug 26
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,031 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$142 nightly
The price is $158
Aug 27 - Aug 28
Total with taxes and fees
Berkshire Mountain Lodge
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (161 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
$136 nightly
The price is $152
Aug 2 - Aug 3
Total with taxes and fees
Micosta Leisure Inn
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
$118 nightly
The price is $132
Aug 3 - Aug 4
Total with taxes and fees
All comforts of home
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
$126 nightly
The price is $141
Aug 3 - Aug 4
Total with taxes and fees
All the comforts of home
Terrace/patio

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (2 reviews)
$328 nightly
The price is $367
Aug 3 - Aug 4
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (262 reviews)
"It was great!"
United States
India
$209 nightly
The price is $226
Aug 3 - Aug 4
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Dining

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$327 nightly
The price is $366
Aug 6 - Aug 7
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
$139 nightly
The price is $155
Aug 11 - Aug 12
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
$242 nightly
The price is $245
Aug 3 - Aug 4
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,485 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
$134 nightly
The price is $150
Aug 11 - Aug 12
Total with taxes and fees
Vacation Village in the Berkshires
Pool

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$374 nightly
The price is $419
Aug 4 - Aug 5
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
Coffee/tea maker, fridge, microwave, oven

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (2 reviews)
"It was a great getaway "
United States
Chandra F.
$165 nightly
The price is $183
Jul 30 - Jul 31
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Interior

Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
$149 nightly
The price is $167
Aug 6 - Aug 7
Total with taxes and fees
Catskill Cottage Walk to Downtown & River Views
Outdoor spa tub

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Ravena
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly. We had a great time."
United States
Richard H.
$208 nightly
The price is $225
Aug 25 - Aug 26
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Interior

Pet Friendly • Fenced Yard • Hot Tub • Romantic

Pet Friendly • Fenced Yard • Hot Tub • Romantic
Ravena
10.0 out of 10, Exceptional, (1 review)
"This was a very quaint cottage type home the owner was very quick with replies. Loved that it had a fenced in yard for our dog. Was scheduled to work at the hospital all weekend, so this was a nice getaway from the hustle and bustle. We’ll stay again if we are ever in the area. "
United States
Sunshine G.
$299 nightly
The price is $323
Aug 3 - Aug 4
Total with taxes and fees
Pet Friendly • Fenced Yard • Hot Tub • Romantic
TV, DVD player, books, video library

1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
$239 nightly
The price is $242
Jul 30 - Jul 31
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"A great little place! We enjoyed the gorgeous property right by the woods. Loved the fire outside at night, and the lobby area was very beautiful. Rooms are small, but they do the trick. You can't tell from the photos, but this place is motel style, even though the rooms are elegant and upscale compared to a motel. Staff were all nice, though usually they are busy doing something or other. Seems to be very minimally staffed, but the staff were all great when we encountered them. They have a nifty self-service ipad at the front where you can do some things yourself, like make new keys if you are locked out of your room. Location is excellent, very close to Lenox, as well as The Mount, Arrrowhead, Ventfort Hall, and more!"
Whitney 2-night trip
Posted 2 hours ago
Berkshires Untold

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental near Chatham is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chatham?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Kinderhook Lake. The Mac-Haydn Theatre and Hudson Chatham Winery are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.