Chatham Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Chatham holiday 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.
The price is HK$1,684
HK$2,791 total
includes taxes & fees
25 May - 26 May
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)
"The place exceeded expectations. Clean, cute space. Roomier than expected. Hot tub was on and at a good temperature. The Main Street with restaurants and bars is literally a 4 minute walk, yet the house feels secluded in a good way. Really enjoyed our stay."
United States
jack h.
The price is HK$1,958
HK$2,464 total
includes taxes & fees
20 May - 21 May
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
9.6 out of 10, Exceptional, (4 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$1,449
HK$2,500 total
includes taxes & fees
18 May - 19 May
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Outdoor dining

Private Yacht on Catskill Creek

Private Yacht on Catskill Creek
Catskill
9.8 out of 10, Exceptional, (28 reviews)
"Host was very responsive and ensured a fun stay for us."
United States
Yannie C.
The price is HK$1,163
HK$2,215 total
includes taxes & fees
18 May - 19 May
Private Yacht on Catskill Creek
Dining

Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.0 out of 10, Wonderful, (11 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$1,022
HK$2,039 total
includes taxes & fees
25 May - 26 May
Charming Yacht on Catskill Creek
Property grounds

Beautiful Yacht on Catskill Creek

Beautiful Yacht on Catskill Creek
Catskill
10.0 out of 10, Exceptional, (21 reviews)
"So much fun for me and my boys to stay. AJ and Melissa are great hosts!"
United States
Amy G.
The price is HK$1,233
HK$2,548 total
includes taxes & fees
18 May - 19 May
Beautiful Yacht on Catskill Creek
1 bedroom, in-room safe, desk, laptop workspace

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (225 reviews)
"Everything was great we can’t wait to return !"
United States
Diana
The price is HK$1,402
HK$1,852 total
includes taxes & fees
1 Jun - 2 Jun
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is HK$775
HK$1,208 total
includes taxes & fees
18 May - 19 May
Taborton Harvest Boulder Pines Cabin in the woods
1 bedroom, free WiFi, bed sheets

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Sand Lake
The price is HK$825
HK$1,263 total
includes taxes & fees
18 May - 19 May
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,359 reviews)
"great stay. "
United States
John
The price is HK$675
HK$840 total
includes taxes & fees
20 May - 21 May
Vacation Village in the Berkshires
Fridge, microwave, oven, stovetop

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$775
HK$1,208 total
includes taxes & fees
18 May - 19 May
Taborton Harvest Timber Trails Unique cabin experience
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.6 out of 10, Exceptional, (39 reviews)
"The house was beautiful, clean, and filled with helpful amenities! "
United States
John C.
The price is HK$1,269
HK$2,736 total
includes taxes & fees
18 May - 19 May
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$768
HK$1,036 total
includes taxes & fees
18 May - 19 May
All comforts of home
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is HK$832
HK$1,107 total
includes taxes & fees
25 May - 26 May
All the comforts of home
Outdoor dining

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)
"Great communication, house was cozy and clean. "
United States
Seth A.
The price is HK$1,410
HK$2,789 total
includes taxes & fees
19 May - 20 May
Charming Cottage in the Heart of Catskill & Pet Friendly
TV

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is HK$1,347
HK$4,228 total
includes taxes & fees
18 May - 19 May
Charles Cottage Near Warren St New Renovation
Gift shop

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"Condo location is great—very centrally located and convenient to get to everything. Room was clean and well maintained. Host is responsive and accommodating. Would call out space is a little tight for a family of 4 but works well for a quick weekend trip. "
United States
Lauren B.
The price is HK$846
HK$1,872 total
includes taxes & fees
18 May - 19 May
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 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$1,237
HK$1,561 total
includes taxes & fees
18 May - 19 May
The Brooks Motel: Exceptional Suite
Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$822
HK$1,846 total
includes taxes & fees
18 May - 19 May
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Terrace/patio

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is HK$1,723
HK$3,192 total
includes taxes & fees
31 May - 1 Jun
Boho Hot Tub Cottage | Pet-Friendly | 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

Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

6/10 Okay
"The hotel is under construction and definitely dated so construction is needed. The AC in our room smelled but we had to have it on as it was stuffy. Beds were comfy. Lots of pillows. New bathroom which was small but nice. Room was clean. Breakfast was good. The hair dryer in our room was broken. We went to the front desk to ask for another and the girl was clueless and of no help. I had just showered and I have long hair so I was late to my daughter’s graduation because I had to wait for my hair to dry. "
Donna 1-night trip
Posted 1 hour ago
Comfort Inn Glenmont - Albany South

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:

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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?

Spacious rustic house in Chatham, NY: This highly rated holiday home rental in Chatham offers a patio, a garden and air conditioning to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Chatham?

With 13 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 Martin Van Buren National Historic Site 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.