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Chatham Holiday Rentals

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Check prices for these dates

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

Our top choices for Chatham holiday 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.
The price is HK$1,961
HK$2,495 total
includes taxes & fees
7 Sept - 8 Sept
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.
The price is HK$2,040
HK$2,601 total
includes taxes & fees
11 Aug - 12 Aug
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.
The price is HK$1,961
HK$3,172 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is HK$2,251
HK$5,078 total
includes taxes & fees
31 Aug - 1 Sept
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
The price is HK$1,063
HK$1,191 total
includes taxes & fees
11 Aug - 12 Aug
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
The price is HK$770
HK$1,038 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is HK$833
HK$1,109 total
includes taxes & fees
10 Aug - 11 Aug
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
The price is HK$742
HK$1,004 total
includes taxes & fees
31 Aug - 1 Sept
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.
The price is HK$549
HK$1,623 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is HK$1,467
HK$2,882 total
includes taxes & fees
16 Aug - 17 Aug
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
The price is HK$1,263
HK$1,703 total
includes taxes & fees
8 Sept - 9 Sept
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.
The price is HK$840
HK$1,755 total
includes taxes & fees
20 Aug - 21 Aug
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
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.
The price is HK$1,024
HK$2,034 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is HK$824
HK$1,924 total
includes taxes & fees
9 Sept - 10 Sept
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.
The price is HK$1,632
HK$3,049 total
includes taxes & fees
9 Sept - 10 Sept
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.
The price is HK$981
HK$1,437 total
includes taxes & fees
10 Aug - 11 Aug
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 traveller
The price is HK$798
HK$1,031 total
includes taxes & fees
12 Aug - 13 Aug
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.
The price is HK$1,440
HK$2,665 total
includes taxes & fees
11 Aug - 12 Aug
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.
The price is HK$1,239
HK$1,564 total
includes taxes & fees
10 Aug - 11 Aug
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 5 hours ago
The Yankee Inn

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Chatham is located near skiing, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chatham?

With 12 Expedia holiday rentals, you're guaranteed 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 wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.