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.

Chatham Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

HOLIDAYS at the PETITE MAISON

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Relax in the Country - Peace, quiet and family friendly

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Home Sweet Home in a Best Place to Live Locale

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beauty in the Berkshires

Rental Home
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Spectacular All Seasons Retreat with Amazing Views

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Heaven Cant Wait, On Beautiful Kinderhook

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!

Rental Home
7 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Designer Home with Panoramic Views near Hudson

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Chatham rentals sent straight to your email!

Cozy yet spacious lakefront cottage, Ideal for all seasons

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Quiet Get Away on the Lake! Kayaks and Fishing Equipments Provided

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Welcome to WIndswept Acres in the Berkshire Mts!

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

A Beautiful Retreat In a Stunning Home and Landscaped Lawns

Rental Home
7 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The Home in Malden Bridge, Columbia County, New York

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Heavenly Kinderhook Lake!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautifully Renovated Exposed Beam House

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Historical Dutch Gem In The Hudson Valley

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Carriage House Charmer

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Farm House on 460 Acre Working Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Modern Cozy Wooded Retreat On 30 Private Acres

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Book Your Summer Getaway Now! Pool, BBQ, Big Skies

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Hudson Old Chatham Loft

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Austerlitz , New York, Columbia County

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Secluded House with Picturesque Views in Historic Old Chatham, NY

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Long term availability Berkshire chalet with hot tub and fast WIFI

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

The hudson old chatham 2 bedroom bungalow

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning New Construction All SeasonLakefront Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection

Pure Berkshire Country Charm! Cozy Winter Work From Home with 1GB WiFi

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy apartment overlooking our small farm. Family Friendly.

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Secluded Family-Friendly Home

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Roaring Rapids Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
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
Payment Protection

Modern Cozy Wooded Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection

Stunning Newer Lakefront Home Near Berkshires wGourmet Kitchen

Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

NEW! Clean & Cozy Hillsdale Cabin, minutes to Catamount, Tanglewood

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Pet-friendly Cozy Farmhouse near Hudson, NY

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Hudson Valley Berkshires Cottage

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection

Ski House -charming house near Catamount/Butternut/ Jiminy Peak

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Cape Cod in Hudson River Valley

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Serene Berkshires Family Vacation Rental on 45 Acres

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Berkshires Hudson Valley View Cottage - Private & Quiet

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Fox Hill Wedding & Events - Wedding And Private Event Venue

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Chalet near 4 ski resorts with hot tub

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection

Spacious secluded yet close to everything

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Tentrr Signature Site - WATER + WOODS

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection

Tentrr Signature Site - WATER + WOODS

Rental Home
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Private Vacation Getaway - Berkshires

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1
Frequently Asked Questions about Chatham