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Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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.
$292 nightly
The price is $329
Sep 8 - Sep 9
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
$307 nightly
The price is $344
Sep 20 - Sep 21
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Dining

3. 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.
$292 nightly
The price is $329
Sep 8 - Sep 9
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
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, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
$658 nightly
The price is $737
Sep 7 - Sep 8
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, (171 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
$133 nightly
The price is $150
Sep 7 - Sep 8
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, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Sep 7 - Sep 8
Total with taxes and fees
All comforts of home
Lobby

7. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,127 reviews)
"Clean & comfortable stay"
United States
Robert
$113 nightly
The price is $126
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge
Property grounds

8. 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
Sep 10 - Sep 11
Total with taxes and fees
All the comforts of home
Terrace/patio

9. 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.
$324 nightly
The price is $363
Sep 7 - Sep 8
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Exterior

10. 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, (293 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
$209 nightly
The price is $226
Sep 7 - Sep 8
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, fridge, microwave, oven

11. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
$204 nightly
The price is $207
Sep 10 - Sep 11
Total with taxes and fees
NEW RENO - Chalet-style farm loft near Tanglewood
Pool

12. 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.
$338 nightly
The price is $379
Sep 7 - Sep 8
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
Lobby

13. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,607 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
$122 nightly
The price is $136
Sep 7 - Sep 8
Total with taxes and fees
Vacation Village in the Berkshires
TV, DVD player, books, video library

14. 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.
$220 nightly
The price is $223
Sep 14 - Sep 15
Total with taxes and fees
1800s Carriage house in Berkshires / Hudson Valley
Terrace/patio

15. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
$339 nightly
The price is $380
Sep 7 - Sep 8
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
Exterior

16. Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (17 reviews)
"This was a dash away and perfect! "
United States
Linda R.
$165 nightly
The price is $183
Sep 6 - Sep 7
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Outdoor spa tub

17. Pet Friendly Glamping • Hot Tub • Fire Pit • Patio

Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Ravena
8.0 out of 10, Very Good, (2 reviews)
"The host was very friendly. We had a great time."
United States
Richard H.
$202 nightly
The price is $218
Sep 14 - Sep 15
Total with taxes and fees
Pet Friendly Glamping • Hot Tub • Fire Pit • Patio
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
$148 nightly
The price is $165
Sep 12 - Sep 13
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Desk, iron/ironing board, WiFi, bed sheets

19. 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
Sep 7 - Sep 8
Total with taxes and fees
The Brooks Motel: Exceptional Suite
Dining

20. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (16 reviews)
"We had never stayed overnight on a boat before and were a little nervous. Now we can't wait to stay on one again! Melissa and AJ were so accommodating and extremely nice....perfect place to stay if seeing a concert at Catskill Point. They dropped us off at concert and picked us up on pontoon - how fun is that? To wake up to a sunny and serene morning while having coffee on the creek was priceless. I never do reviews but felt compelled to do this one only because if you are having...
United States
Frances K.
$235 nightly
The price is $263
Sep 8 - Sep 9
Total with taxes and fees
Charming Yacht on Catskill Creek
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

10/10 Excellent
"Unit was clean and comfortable. Staff was friendly and helpful."
Edwina 2-night trip
Posted 1 hour 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 $126 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?

Catskill Cottage Walk to Downtown & River Views: This vacation home near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site 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.