Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Chatham vacation rentals

Outdoor spa tub
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"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.
$355 nightly
The price is $400
Jan 6 - Jan 7
Total with taxes and fees
HunnyHAUS: Deluxe TINY*private spa*walk to town
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

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)
"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
Jan 6 - Jan 7
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds
Sugar Shack - 300 square feet of pure sweetness.

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)
"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.
$303 nightly
The price is $342
Jan 7 - Jan 8
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$186 nightly
The price is $208
Jan 18 - Jan 19
Total with taxes and fees
Huttopia Berkshires
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2202)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 6 - Jan 7
Total with taxes and fees
Vacation Village in the Berkshires
Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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, (118)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
$150 nightly
The price is $162
Jan 13 - Jan 14
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
$133 nightly
The price is $150
Jan 9 - Jan 10
Total with taxes and fees
Micosta Leisure Inn
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very Good, (988)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
$219 nightly
The price is $245
Jan 6 - Jan 7
Total with taxes and fees
Jiminy Peak Mountain Resort
Exterior detail
Charming loft cottage in tranquil Germantown with WiFi, AC

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, (8)
"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.
$191 nightly
The price is $214
Jan 6 - Jan 7
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds
All comforts of home

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Jan 6 - Jan 7
Total with taxes and fees
All comforts of home
Exterior
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
$335 nightly
The price is $371
Jan 6 - Jan 7
Total with taxes and fees
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Outdoor spa tub
Tiny Home w/ Hot Tub and Sunset View!

Tiny Home w/ Hot Tub and Sunset View!

Tiny Home w/ Hot Tub and Sunset View!
Selkirk
10.0 out of 10, Exceptional, (2)
"Very nice place. Was in a quiet area and hosts were great."
United States
Brian H.
$111 nightly
The price is $120
Jan 7 - Jan 8
Total with taxes and fees
Tiny Home w/ Hot Tub and Sunset View!
Property grounds
All the comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29)
"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.
$126 nightly
The price is $141
Jan 6 - Jan 7
Total with taxes and fees
All the comforts of home
Dining tables
2 bed room Apartment

2 bed room Apartment

2 bed room Apartment
South End
8.8 out of 10, Excellent, (8)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
$165 nightly
The price is $178
Jan 12 - Jan 13
Total with taxes and fees
2 bed room Apartment
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
$223 nightly
The price is $237
Jan 6 - Jan 7
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
$165 nightly
The price is $183
Jan 6 - Jan 7
Total with taxes and fees
Taborton Harvest Boulder Pines Cabin in the woods
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Jan 6 - Jan 7
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

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, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$271 nightly
The price is $303
Jan 6 - Jan 7
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
$271 nightly
The price is $303
Jan 6 - Jan 7
Total with taxes and fees
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
TV, offices
The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$179 nightly
The price is $200
Jan 6 - Jan 7
Total with taxes and fees
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, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room was cozy and clean. Loved the fireplace & view. Great price too. Cameron at the front desk was pleasant and working hard the several times we saw him. Pool was warm & hot tub was nice! Overall, great stay! Will definitely stay again! "
Kimberly 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

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 $141 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?

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.