We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Vacation Rentals
Restaurants
Things to do
Skip to main content
Review
Trips
Alerts
Sign in
Inbox
See all
Sign in
to get trip updates and message other travelers.
Chatham
Chatham Tourism
Chatham Hotels
Chatham Vacation Rentals
Chatham Vacation Packages
Flights to Chatham
Things to Do in Chatham
Chatham Travel Forum
Chatham Photos
Chatham Map
Chatham Travel Guide
Hotels
All Chatham Hotels
Chatham Hotel Deals
By Hotel Class
Popular Chatham Categories
Near Airports
5-stars Hotels in Chatham
4-stars Hotels in Chatham
3-stars Hotels in Chatham
Chatham Motels
Hotels near (ALB) Albany Intl Airport
Things to do
Restaurants
Flights
Vacation Rentals
Shopping
Vacation Packages
Cruises
Rental Cars
Tours
Add a Place
Travel Forum
Airlines
Best of 2022
Road Trips
Help Center
Travel Articles
Vacation Rentals in Chatham, NY
Vacation Rentals
USA
New York (NY)
Vacation Rentals in Chatham, NY
Search
Chatham Vacation Rentals
List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
View Map
Bedrooms
Any
Bathrooms
Any
Amenities
Parking (47)
Internet (43)
Air Conditioning (43)
Washer/Dryer (42)
Show more
Suitability
Kid friendly (41)
Elder access (3)
Smoking allowed (2)
Pet friendly (1)
Show more
Property type
Vacation Rental House (47)
Condominium/Apartment (3)
Cabin Vacation Rental (0)
Private Room (0)
Show more
Distinctive Features
Boat Available (6)
Waterfront (2)
Water Views (2)
Housekeeping Included (2)
Show more
Distance from
1 mi
50 rentals
in Chatham.
Sort by:
Tripadvisor Sort
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
30 reviews
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
HOLIDAYS at the PETITE MAISON
7 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Relax in the Country - Peace, quiet and family friendly
5 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Home Sweet Home in a Best Place to Live Locale
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beauty in the Berkshires
99 reviews
Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
Spectacular All Seasons Retreat with Amazing Views
37 reviews
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Heaven Cant Wait, On Beautiful Kinderhook
58 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!
57 reviews
Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check in
Check out
Show Prices
Designer Home with Panoramic Views near Hudson
33 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!
21 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Save time - get the best
Chatham
rentals sent straight to your email!
Get the List
Cozy yet spacious lakefront cottage, Ideal for all seasons
22 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
Quiet Get Away on the Lake! Kayaks and Fishing Equipments Provided
27 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
16 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Welcome to WIndswept Acres in the Berkshire Mts!
14 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
A Beautiful Retreat In a Stunning Home and Landscaped Lawns
13 reviews
Rental Home
7 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
The Home in Malden Bridge, Columbia County, New York
16 reviews
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Heavenly Kinderhook Lake!
15 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautifully Renovated Exposed Beam House
14 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check in
Check out
Show Prices
Historical Dutch Gem In The Hudson Valley
14 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Carriage House Charmer
9 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Charming Farm House on 460 Acre Working Farm
10 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Modern Cozy Wooded Retreat On 30 Private Acres
14 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Book Your Summer Getaway Now! Pool, BBQ, Big Skies
9 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Hudson Old Chatham Loft
13 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
More info
Check in
Check out
Show Prices
Austerlitz , New York, Columbia County
7 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Secluded House with Picturesque Views in Historic Old Chatham, NY
4 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Long term availability Berkshire chalet with hot tub and fast WIFI
5 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
The hudson old chatham 2 bedroom bungalow
4 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Stunning New Construction All SeasonLakefront Home
3 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Pure Berkshire Country Charm! Cozy Winter Work From Home with 1GB WiFi
5 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Cozy apartment overlooking our small farm. Family Friendly.
2 reviews
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Secluded Family-Friendly Home
2 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Roaring Rapids Cottage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Total Privacy! Tanglewood Retreat With Berkshire Views!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Modern Cozy Wooded Retreat
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Pet-friendly Cozy Farmhouse near Hudson, NY
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check in
Check out
Show Prices
Hudson Valley Berkshires Cottage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Ski House -charming house near Catamount/Butternut/ Jiminy Peak
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Charming Cape Cod in Hudson River Valley
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Serene Berkshires Family Vacation Rental on 45 Acres
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Berkshires Hudson Valley View Cottage - Private & Quiet
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check in
Check out
Show Prices
Fox Hill Wedding & Events - Wedding And Private Event Venue
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Chalet near 4 ski resorts with hot tub
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Spacious secluded yet close to everything
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Tentrr Signature Site - WATER + WOODS
Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Payment Protection
Tentrr Signature Site - WATER + WOODS
Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match:
Sleeps
More info
Check in
Check out
Show Prices
Private Vacation Getaway - Berkshires
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check in
Check out
Show Prices
Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm
Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check in
Check out
Show Prices
Previous
Next
1
Frequently Asked Questions about Chatham
Do any vacation rentals in Chatham have a pool?
Yes, here are some popular vacation rentals in Chatham that have a pool:\n
\n
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
\n
Relax in the Country - Peace, quiet and family friendly
\n
Home Sweet Home in a Best Place to Live Locale
\n
\n
See all vacation rentals with a pool in Chatham on Tripadvisor
Do any vacation rentals in Chatham have internet access?
Yes, here are some popular vacation rentals in Chatham that have internet access:\n
\n
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
\n
Relax in the Country - Peace, quiet and family friendly
\n
Home Sweet Home in a Best Place to Live Locale
\n
\n
See all vacation rentals in Chatham on Tripadvisor
What are the best pet friendly rentals in Chatham?
The best pet friendly rentals in Chatham are:\n
\n
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
\n
Relax in the Country - Peace, quiet and family friendly
\n
Home Sweet Home in a Best Place to Live Locale
\n
\n
See all pet friendly vacation rentals in Chatham on Tripadvisor
What are some great rentals in Chatham that are kid friendly?
Some of the most popular kid friendly rentals in Chatham are:\n
\n
CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI/ 1NIGHT CANYON RANCH CHEF AVAILABLE
\n
Relax in the Country - Peace, quiet and family friendly
\n
HOLIDAYS at the PETITE MAISON
\n
\n
See all kid friendly vacation rentals in Chatham on Tripadvisor