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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chatham vacation rentals

Terrace/patio

1. 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.
$282 nightly
The price is $318
Sep 7 - Sep 8
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Dining

2. 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.
$294 nightly
The price is $332
Aug 11 - Aug 12
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Property grounds

3. 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.
$361 nightly
The price is $404
Aug 10 - Aug 11
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Exterior detail

4. 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.
$578 nightly
The price is $647
Aug 31 - Sep 1
Total with taxes and fees
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Exterior

5. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 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 11 - Aug 12
Total with taxes and fees
Micosta Leisure Inn
Property grounds

6. 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 10 - Aug 11
Total with taxes and fees
All comforts of home
Property grounds

7. 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 10 - Aug 11
Total with taxes and fees
All the comforts of home
Lobby

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,054 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
$140 nightly
The price is $154
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Coffee/tea maker, fridge, microwave, oven

9. 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.
$226 nightly
The price is $229
Aug 13 - Aug 14
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Terrace/patio

10. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
$328 nightly
The price is $367
Aug 16 - Aug 17
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Exterior

11. 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, (266 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
$201 nightly
The price is $217
Sep 8 - Sep 9
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Outdoor spa tub

12. 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.
$207 nightly
The price is $224
Aug 20 - Aug 21
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Dining

13. Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
$363 nightly
The price is $406
Aug 14 - Aug 15
Total with taxes and fees
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Dining

14. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (16 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
$232 nightly
The price is $259
Aug 10 - Aug 11
Total with taxes and fees
Charming Yacht on Catskill Creek
TV, DVD player, books, video library

15. 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.
$242 nightly
The price is $245
Sep 9 - Sep 10
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Pool

16. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$347 nightly
The price is $389
Sep 9 - Sep 10
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
Coffee/tea maker, fridge, microwave, oven

17. 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
Aug 10 - Aug 11
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Interior

18. Magic Forest Farm's Enchanted Cabin

Magic Forest Farm's Enchanted Cabin
Coeymans Hollow
9.6 out of 10, Exceptional, (12 reviews)
"Such a cute little cabin. Great place to get some rest to break up a long drive. "
United States
Anonymous traveler
$122 nightly
The price is $131
Aug 12 - Aug 13
Total with taxes and fees
Magic Forest Farm's Enchanted Cabin
Interior

19. 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.
$311 nightly
The price is $336
Sep 9 - Sep 10
Total with taxes and fees
Pet Friendly • Fenced Yard • Hot Tub • Romantic
Desk, iron/ironing board, WiFi, bed sheets

20. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$178 nightly
The price is $199
Aug 10 - Aug 11
Total with taxes and fees
The Brooks Motel: Exceptional Suite
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The staff were friendly, helpful with finding restaurants and other local attractions. Our room was immaculate and nicely furnished with modern furnishings in great condition. The room was quiet--we never heard our neighbors. It was pleasant to sit on the balcony and read. The location is great, 15 or 20 mins to Tanglewood depending on time. A very nice breakfast with lots of choices. We would definitely recommend this Inn to friends, and plan to return for future trips to Tanglewood and The Berkshires. ."
John 2-night trip
Posted 1 hour ago
The Yankee Inn

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 $143 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 4 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 Queechy Lake 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.