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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chatham vacation rentals

Dining

1. 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.
$297 nightly
The price is $335
Sep 17 - Sep 18
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Terrace/patio

2. 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.
$303 nightly
The price is $342
Aug 24 - Aug 25
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
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.
$366 nightly
The price is $410
Aug 23 - Aug 24
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.
$549 nightly
The price is $615
Sep 13 - Sep 14
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, (168 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
$139 nightly
The price is $155
Aug 24 - Aug 25
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 24 - Aug 25
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 24 - Aug 25
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, (1,077 reviews)
"A nice place to stay in the Berkshires."
United States
Robert
$125 nightly
The price is $139
Aug 31 - Sep 1
Total with taxes and fees
Berkshire Mountain Lodge
Exterior

9. 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, (275 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
$201 nightly
The price is $217
Sep 17 - Sep 18
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, fridge, microwave, oven

10. 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.
$200 nightly
The price is $202
Aug 19 - Aug 20
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Terrace/patio

11. 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 24 - Aug 25
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
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.
$208 nightly
The price is $225
Aug 27 - Aug 28
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Pool

13. 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.
$349 nightly
The price is $391
Sep 9 - Sep 10
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
Interior

14. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (26 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
$149 nightly
The price is $167
Aug 20 - Aug 21
Total with taxes and fees
Catskill Cottage Walk to Downtown & River Views
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.
$236 nightly
The price is $239
Sep 14 - Sep 15
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Desk, iron/ironing board, WiFi, bed sheets

16. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
$170 nightly
The price is $190
Aug 19 - Aug 20
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Dining

17. 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.
$236 nightly
The price is $264
Aug 20 - Aug 21
Total with taxes and fees
Charming Yacht on Catskill Creek
Coffee/tea maker, fridge, microwave, oven

18. 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.
$166 nightly
The price is $184
Aug 19 - Aug 20
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Outdoor dining

19. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$320 nightly
The price is $358
Aug 21 - Aug 22
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Coffee/tea maker, fridge, microwave, oven

20. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$139 nightly
The price is $155
Aug 31 - Sep 1
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Large resort with many amenities -- 2 pools, grills, volleyball court, extensive walking paths. GREAT for a family of kids since there are a lot of events planned for them by resort. Beautiful setting. Our two-suite rental roomy, comfortable, well-equipped. Have come here for years. Love little balcony overlooking greenery AND gas fireplace."
Christine 3-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

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 $127 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.