Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Chatham vacation rentals

Fridge, microwave, oven, stovetop

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is ￥33,996
￥63,297 total
includes taxes & fees
Jan 29 - Jan 30
HunnyHAUS: Deluxe TINY*private spa*walk to town
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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 ￥33,996
￥57,058 total
includes taxes & fees
Jan 28 - Jan 29
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, (6 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 ￥33,996
￥57,058 total
includes taxes & fees
Jan 20 - Jan 21
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
Chatham
The price is ￥27,753
￥48,313 total
includes taxes & fees
Jan 25 - Jan 26
Renovated house. Built in 1890s. No neighbors in sight.
Exterior

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ￥30,240
￥33,778 total
includes taxes & fees
Jan 18 - Jan 19
Huttopia Berkshires
View from property

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, (130 reviews)
"I loved every single part of the stay "
United States
Srijana
The price is ￥17,337
￥25,556 total
includes taxes & fees
Jan 27 - Jan 28
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,210 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,440
￥20,099 total
includes taxes & fees
Jan 27 - Jan 28
Vacation Village in the Berkshires
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (135 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
Micosta Leisure Inn
Outdoor dining

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,904
￥50,987 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
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, (1 review)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is ￥19,765
￥28,960 total
includes taxes & fees
Jan 26 - Jan 27
Taborton Harvest Timber Trails Unique cabin experience
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, (21 reviews)
"Perfect place for a visit to the Hudson Valley. Very comfortable and well taken care of. Friendly neighbors. 3 blocks from Downtown Catskill"
United States
Kirk N.
The price is ￥15,415
￥38,572 total
includes taxes & fees
Jan 21 - Jan 22
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is ￥17,235
￥34,002 total
includes taxes & fees
Jan 21 - Jan 22
Charming loft cottage in tranquil Germantown with WiFi, AC
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is ￥21,662
￥43,625 total
includes taxes & fees
Jan 19 - Jan 20
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Exterior

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥34,628
￥38,680 total
includes taxes & fees
Jan 22 - Jan 23
Jiminy Peak Mountain Resort
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is ￥18,658
￥24,439 total
includes taxes & fees
Feb 2 - Feb 3
All the comforts of home
Interior

Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers
Stephentown
7.0 out of 10, Good, (2 reviews)
"It’s a duplex, half of an old farm house. The bedrooms are all up a steep staircase to the second floor. The only bathroom is on the main floor with the kitchen and LR. It was clean but had a mild old house smell. It’s out in the country with a great view from the enclosed porch and the open deck. The kitchen was well stocked with appliances and everything worked. It needs more seating and lights in the LR. "
United States
Bill B.
The price is ￥24,509
￥51,250 total
includes taxes & fees
Jan 26 - Jan 27
Charming 3-bedroom Cabin for nature lovers
Exterior

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

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.8 out of 10, Exceptional, (35 reviews)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
The price is ￥23,481
￥51,829 total
includes taxes & fees
Jan 21 - Jan 22
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ￥30,992
￥87,540 total
includes taxes & fees
Jan 22 - Jan 23
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Smart TV

2 bed room Apartment

2 bed room Apartment
South End
8.8 out of 10, Excellent, (8 reviews)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is ￥15,066
￥28,261 total
includes taxes & fees
Jan 20 - Jan 21
2 bed room Apartment
Property grounds

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (52 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,512
￥20,913 total
includes taxes & fees
Jan 23 - Jan 24
All comforts of home
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
"It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds. "
Maria 4-night trip
Posted 22 hours ago
Vacation Village in the Berkshires

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 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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Chatham offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable 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 selection of games and a hot tub.

How many vacation rentals are there in Chatham?

With 13 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 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.