Old 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 Old Chatham vacation rentals

TV, fireplace
Artists’ Hideaway in Old Chatham

Vacation Home in Old Chatham

Artists’ Hideaway in Old Chatham
$493 nightly
The price is $552
Jan 4 - Jan 5
Total with taxes and fees
Artists’ Hideaway in Old Chatham
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
$194 nightly
The price is $217
Jan 18 - Jan 19
Total with taxes and fees
Huttopia Berkshires
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
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.

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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.
$320 nightly
The price is $361
Jan 12 - Jan 13
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2197)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Jan 4 - Jan 5
Total with taxes and fees
Vacation Village in the Berkshires
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Cabin in Sand Lake

Taborton Harvest Timber Trails Unique cabin experience
10.0 out of 10, Exceptional, (1)
"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.
$165 nightly
The price is $183
Jan 2 - Jan 3
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
Balcony
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
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
Fridge, microwave, oven, stovetop
Newly Renovated Gem in Melrose - Pet Friendly

Apartment in Albany

Newly Renovated Gem in Melrose - Pet Friendly
10.0 out of 10, Exceptional, (8)
"Very nice space. Just what I was looking for"
United States
Isadora S.
$190 nightly
The price is $206
Jan 6 - Jan 7
Total with taxes and fees
Newly Renovated Gem in Melrose - Pet Friendly
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
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 3 - Jan 4
Total with taxes and fees
All comforts of home
Fridge, microwave, oven, stovetop
Business Travelers Retreat

Apartment in Albany

Business Travelers Retreat
10.0 out of 10, Exceptional, (1)
"Place was as advertised and Rodney was a great host. Very responsive. Location was ideal for the Capital Region and parking was super convenient. Highly reccomend."
United States
Chas K.
Business Travelers Retreat
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
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.
$229 nightly
The price is $244
Jan 3 - Jan 4
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Smart TV, books
Chic Madison Parkview

Apartment in Albany

Chic Madison Parkview
9.6 out of 10, Exceptional, (33)
"Location close to restaurants and parks."
United States
Alex B.
$162 nightly
The price is $175
Jan 2 - Jan 3
Total with taxes and fees
Chic Madison Parkview
Terrace/patio
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
$330 nightly
The price is $366
Jan 4 - Jan 5
Total with taxes and fees
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Smart TV
The Rizzy Apartment

Apartment in Washington Square

The Rizzy Apartment
7.2 out of 10, Good, (10)
"Great time "
United States
Patrick
$132 nightly
The price is $142
Jan 5 - Jan 6
Total with taxes and fees
The Rizzy Apartment
WiFi
Chic, Renovated Brownstone in Prime DT Albany

Apartment in Arbor Hill

Chic, Renovated Brownstone in Prime DT Albany
8.0 out of 10, Very Good, (1)
$197 nightly
The price is $213
Jan 2 - Jan 3
Total with taxes and fees
Chic, Renovated Brownstone in Prime DT Albany
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
$185 nightly
The price is $203
Jan 4 - Jan 5
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Outdoor spa tub
Tiny Home w/ Hot Tub and Sunset View!

Vacation Home in Selkirk

Tiny Home w/ Hot Tub and Sunset View!
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

Vacation Home in Hudson

All the comforts of home
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 2 - Jan 3
Total with taxes and fees
All the comforts of home
Property grounds
❣️Historic, Spacious & Fun 2BR Apt @ Downtown Albany

Apartment in Pastures

❣️Historic, Spacious & Fun 2BR Apt @ Downtown Albany
8.6 out of 10, Excellent, (24)
"We want to thank the host. Nice apartment. Great location near our Rotary Conference and easy to access. The tub was not available for a bath but that was the only thing."
United States
Charles G.
$182 nightly
The price is $196
Jan 18 - Jan 19
Total with taxes and fees
❣️Historic, Spacious & Fun 2BR Apt @ Downtown Albany
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$230 nightly
The price is $257
Jan 5 - Jan 6
Total with taxes and fees
Home in Great Barrington
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 Old Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"great stall and friendly pet friendly place"
bonnie 2-night trip
Posted 20 hours ago
Berkshire Mountain Lodge

Find out more about Old Chatham

Everything you need to know about Old 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 Old 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 Old Chatham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Chatham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old 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 Old 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 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 Old Chatham rentals

At Expedia, we put the best Old 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 Old 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 Old 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 Old 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 Old Chatham?

Yes, we offer vacation rentals close to well known points of interest in Old Chatham, or you can choose a more remote option if you'd like a relaxing place to stay. Old Chatham is known for its museums.

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

5 Star Private Estate w/ Pool, Pond, Gym, Trail, Library, Arcade! Book by 12/31!: Visitors like this Old Chatham vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a library so you can immerse yourself in your vacation.

How many vacation rentals will I find in Old Chatham?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Old Chatham stay.

What’s there to see and do in Old Chatham?

Enjoy the area's cultural attractions such as Shaker Museum and Library, or get outdoors into nature at a spot like Kinderhook Lake. Queechy Lake and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What’s a vacation rental in Old Chatham like?

Vacation rentals are privately owned properties you can book for several days or longer in Old Chatham. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.