Old Chatham Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Rentals in Old Chatham

Interior
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
$418 nightly
The price is $468
Dec 1 - Dec 2
Total with taxes and fees
Artists’ Hideaway in Old Chatham
Terrace/patio
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.
$325 nightly
The price is $366
Dec 1 - Dec 2
Total with taxes and fees
Sugar Shack - 300 square feet of pure sweetness.
Exterior
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
$170 nightly
The price is $190
Dec 17 - Dec 18
Total with taxes and fees
Huttopia Berkshires
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)
"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.
$325 nightly
The price is $366
Dec 1 - Dec 2
Total with taxes and fees
BLUSH: Boutique TINY home*private spa*walk to town
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
$94 nightly
The price is $105
Nov 29 - Nov 30
Total with taxes and fees
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
$149 nightly
The price is $166
Nov 30 - Dec 1
Total with taxes and fees
Jiminy Peak Mountain Resort
Dining tables
2 bed room Apartment

2 bed room Apartment

South End
10.0 out of 10, Exceptional, (5)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
$165 nightly
The price is $178
Nov 30 - Dec 1
Total with taxes and fees
2 bed room Apartment
Smart TV, books
Chic Madison Parkview

Chic Madison Parkview

Albany
9.6 out of 10, Exceptional, (31)
"Location close to restaurants and parks."
United States
Alex B.
$162 nightly
The price is $175
Nov 29 - Nov 30
Total with taxes and fees
Chic Madison Parkview
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)
"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
Nov 29 - Nov 30
Total with taxes and fees
Taborton Harvest Timber Trails Unique cabin experience
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

Hancock
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
$212 nightly
The price is $237
Dec 3 - Dec 4
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Property grounds
All comforts of home

All comforts of home

Hudson
9.8 out of 10, Exceptional, (51)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Dec 1 - Dec 2
Total with taxes and fees
All comforts of home
1 bedroom, desk, iron/ironing board, free WiFi
Albany Business Class Apartment

Albany Business Class Apartment

2.0 star property
Center Square
9.0 out of 10, Wonderful, (2)
" this place is perfect for short or long stay. Host was attentive to any needs!! Highly recommended:)"
United States
Gaudy H.
$174 nightly
The price is $188
Dec 1 - Dec 2
Total with taxes and fees
Albany Business Class Apartment
Outdoor spa tub
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.
$120 nightly
The price is $130
Dec 2 - Dec 3
Total with taxes and fees
Tiny Home w/ Hot Tub and Sunset View!
Smart TV, video games, stereo, printers
✨Historic Full Amenities 2BR Apt @ Downtown Albany

✨Historic Full Amenities 2BR Apt @ Downtown Albany

Pastures
9.0 out of 10, Wonderful, (18)
"Good place to rest after an active day "
United States
Julie B.
$184 nightly
The price is $198
Nov 30 - Dec 1
Total with taxes and fees
✨Historic Full Amenities 2BR Apt @ Downtown Albany
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
$189 nightly
The price is $208
Nov 30 - Dec 1
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$212 nightly
The price is $237
Dec 3 - Dec 4
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Fridge, microwave, oven, stovetop
Business Travelers Retreat

Business Travelers Retreat

Albany
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.
$171 nightly
The price is $185
Nov 30 - Dec 1
Total with taxes and fees
Business Travelers Retreat
Fridge, microwave, oven, stovetop
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.
$213 nightly
The price is $227
Nov 30 - Dec 1
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (28)
"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
Nov 30 - Dec 1
Total with taxes and fees
All the 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.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Chatham Hotel Reviews

Albany Plaza Hotel

Albany Plaza Hotel

10/10 Excellent
"It served its purpose, was fairly dates and a bit on the dirty side. Overall it was what you would expect. Staff were all amazing and very helpful!"
Dylan 1-night trip
Posted 1 day ago
Albany Plaza Hotel

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 $105 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?

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!: 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 5 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.