Search Vacation Homes in Old Chatham

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Vacation Homes 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
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
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!
Exterior
Albany Retreat- Free Breakfast & Parking Included

Albany Retreat- Free Breakfast & Parking Included

West End
$68 nightly
The price is $73
Nov 30 - Dec 1
Total with taxes and fees
Albany Retreat- Free Breakfast & Parking Included
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
$243 nightly
The price is $271
Dec 15 - Dec 16
Total with taxes and fees
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$217 nightly
The price is $242
Dec 1 - Dec 2
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$482 nightly
The price is $523
Dec 6 - Dec 7
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
$326 nightly
The price is $365
Nov 30 - Dec 1
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Modern & Cozy Cntr Square Townhouse Gem from 1854

Modern & Cozy Cntr Square Townhouse Gem from 1854

Albany
10.0 out of 10, Exceptional, (62)
"Great stay, thank you"
United States
Olga K.
$242 nightly
The price is $261
Dec 1 - Dec 2
Total with taxes and fees
Modern & Cozy Cntr Square Townhouse Gem from 1854
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$441 nightly
The price is $493
Dec 2 - Dec 3
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop
Modern and Cozy Pine Hills Home from Early 1900s

Modern and Cozy Pine Hills Home from Early 1900s

Pine Hills
10.0 out of 10, Exceptional, (56)
"This was an excellent stay! Clean, comfortable, and responsive hosts. Will stay again if back in that area. "
United States
Amy S.
$239 nightly
The price is $259
Dec 3 - Dec 4
Total with taxes and fees
Modern and Cozy Pine Hills Home from Early 1900s
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.4 out of 10, Exceptional, (6)
$253 nightly
The price is $283
Nov 30 - Dec 1
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Terrace/patio
Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!

West Sand Lake
10.0 out of 10, Exceptional, (8)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
$355 nightly
The price is $394
Dec 1 - Dec 2
Total with taxes and fees
Treat yourself at the stunning June Farms Wellness Huts!
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape

2.0 star property
Stottville
$302 nightly
The price is $306
Dec 3 - Dec 4
Total with taxes and fees
Hudson Hot Tub & Pet Escape
Private kitchen
Honey Comb Hideout 3Br. House Albany

Honey Comb Hideout 3Br. House Albany

Albany
$514 nightly
The price is $555
Nov 30 - Dec 1
Total with taxes and fees
Honey Comb Hideout 3Br. House Albany
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
$490 nightly
The price is $547
Nov 30 - Dec 1
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$464 nightly
The price is $518
Nov 30 - Dec 1
Total with taxes and fees
Great Barrington Get Away
Outdoor dining
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany

Pine Hills
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at this property and will rent again when in the area. The owners were very responsive and great to work with. The apt was beautiful and immaculate. We enjoyed our stay very much. The only area that was perfect was the outside stairs to the front door— uneven, steep, etc. We had older guest with us and this was concerning. But we managed. Thanks again for a great stay"
United States
Melissa A.
$428 nightly
The price is $462
Dec 14 - Dec 15
Total with taxes and fees
“The Allen House” Charming 3-Bed / 2-Bath Sleeps 8. Fantastic location in Albany
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
10.0 out of 10, Exceptional, (57)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
$477 nightly
The price is $534
Nov 30 - Dec 1
Total with taxes and fees
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Living area
Charming 3-bedroom house with pool table

Charming 3-bedroom house with pool table

Pine Hills
7.6 out of 10, Good, (4)
"We had a great stay as we played one night at the Empire. The house is very quaint and there is ample shared parking in the back. If ever we come back to Albany, I'll be sure to consider this house. "
United States
Chiqui R.
$367 nightly
The price is $396
Dec 7 - Dec 8
Total with taxes and fees
Charming 3-bedroom house with pool table
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

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

10/10 Excellent
"The room was great and cleaned. Breakfast was fantastic. The buffet choices were great. The atmosphere of the entire place was just wonderful. The host at the desk, Laniya was great at helping us check in after we had some issues with a third party app. Will definitely stay here again when I am in town! "
ZaVea 1-night trip
Posted 2 days ago
Hyatt Place Albany/Downtown

Find out more about Old Chatham

Old Chatham Vacation Homes information

Number of reviews
357
Accommodation
465 Vacation Homes
Lowest Price
$73
Highest Price
$555

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