Top 50 Chatham Vacation Rentals

Houses (331)
Apartments (56)
Cottages (47)
Golf rental (404)
Ski rental (213)
Mountain view (207)

Explore a selection of Chatham vacation rentals

Modern Cozy Wooded Retreat On 30 Private Acres
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$234 avg/night
2 beds
2 Bathrooms
Guests 6
6 reviews
Spectacular all season well equipped, private retreat with...
Guests24
Bedrooms7
Bathrooms4
Wonderful 5 / 5
$728 avg/night
7 beds
4 Bathrooms
Guests 24
17 reviews
Designer's Home In Idylic Country Setting, Near Hudson, Chatham...
Guests8
Bedrooms3
Bathroom1
Wonderful 5 / 5
$475 avg/night
3 beds
1 Bathroom
Guests 8
3 reviews
Modern and cozy, nestled on a private perch above Chatham village.
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$225 avg/night
3 beds
2 Bathrooms
Guests 8
5 reviews
Quiet Country Living
Guests7
Bedrooms4
Bathrooms3
Wonderful 0 / 5
$400 avg/night
4 beds
3 Bathrooms
Guests 7
Peace, Quiet and close to The Berkshires and Hudson
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$200 avg/night
3 beds
2 Bathrooms
Guests 6
3 reviews
Breathtaking Views of the Berkshires & Catskills, Gorgeous Newl...
Guests10
Bedrooms4
Bathrooms3
Wonderful 0 / 5
$750 avg/night
4 beds
3 Bathrooms
Guests 10
Secluded Woodland Retreat - Berkshires, Hudson Valley
Guests4
Bedroom1
Bathroom1
Wonderful 4.5 / 5
$153 avg/night
1 bed
1 Bathroom
Guests 4
6 reviews
Chatham Village Hideaway
Guests2
Studio
Bathroom1
Wonderful 0 / 5
$275 avg/night
Studio
1 Bathroom
Guests 2
Country Estate-Year Round Resort - Pool and Hot tub
Guests10
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$500 avg/night
4 beds
3 Bathrooms
Guests 10
15 reviews
Two Ponds: Unique, Contemporary Compound with Magical Views in...
Guests13
Bedrooms5
Bathrooms4
Wonderful 0 / 5
$1,116 avg/night
5 beds
4 Bathrooms
Guests 13
Spectacular River Views-Luxury Chalet w/ Indoor Pool & Spa on 23...
Guests4
Bedroom1
Bathrooms2
Wonderful 4.9 / 5
$398 avg/night
1 bed
2 Bathrooms
Guests 4
56 reviews
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and...
Guests20
Bedrooms6
Bathrooms5
Wonderful 4.9 / 5
$703 avg/night
6 beds
5 Bathrooms
Guests 20
37 reviews
Idyllic Berkshire Get Away: Balance of relaxation and convenience
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.2 / 5
$114 avg/night
3 beds
2 Bathrooms
Guests 6
5 reviews
Minutes from downtown Great Barrington, Convenient location
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.7 / 5
$325 avg/night
4 beds
3 Bathrooms
Guests 8
7 reviews
Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox...
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$361 avg/night
4 beds
3 Bathrooms
Guests 12
35 reviews
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town...
Guests10
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$260 avg/night
3 beds
3 Bathrooms
Guests 10
20 reviews
Cultural Playground of the East 2+ bed Cottage, 5 mins walk to the...
Guests7
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
2 beds
2 Bathrooms
Guests 7
14 reviews
Family and Dog Friendly Retreat from the City ! (insta/fb...
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.9 / 5
$480 avg/night
4 beds
2 Bathrooms
Guests 10
7 reviews
Quiet Renovated Barn
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$89 avg/night
1 bed
1 Bathroom
Guests 3
17 reviews
A Small Oasis in the Heart of Lenox
Guests3
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$152 avg/night
1 bed
1 Bathroom
Guests 3
37 reviews
Camp Kinderhook Lake House
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.8 / 5
$164 avg/night
4 beds
2 Bathrooms
Guests 10
33 reviews
Cozy Modern Berkshires Rental (mins From Lenox, Kripalu...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$127 avg/night
2 beds
1 Bathroom
Guests 6
16 reviews
Chic Berkshire Carriage House
Guests5
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$200 avg/night
2 beds
1 Bathroom
Guests 5
23 reviews
The Red Cottage on Copake Lake - A Stylishly Updated Home
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$178 avg/night
3 beds
2 Bathrooms
Guests 6
9 reviews
Romantic Retreat Overlooking Lake
Guests5
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$250 avg/night
1 bed
1 Bathroom
Guests 5
36 reviews
General Williams Estate House Lenox/Stockbridge
Guests16
Bedrooms6
Bathrooms5
Wonderful 5 / 5
$849 avg/night
6 beds
5 Bathrooms
Guests 16
19 reviews
Beautiful Berkshire Cabin Close to All Attractions and Beach
Guests8
Bedrooms2
Bathroom1
Wonderful 4.1 / 5
$175 avg/night
2 beds
1 Bathroom
Guests 8
15 reviews
Lovely Catskill Views, Close to Hudson, 5 minutes from Lake...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$417 avg/night
4 beds
3 Bathrooms
Guests 10
24 reviews
Luxury Living at the Lake
Guests15
Bedrooms5
Bathrooms4
Wonderful 4.9 / 5
$478 avg/night
5 beds
4 Bathrooms
Guests 15
28 reviews
Sunny, Large, Home with beautiful gardens on pond. Walking...
Guests10
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$199 avg/night
3 beds
2 Bathrooms
Guests 10
6 reviews
Nature Lover's Paradise close to everything the Berkshires has to...
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$250 avg/night
2 beds
2 Bathrooms
Guests 4
9 reviews
Restored 1780 Cottage Nestled In The Pastures Of Kinderhook Farm
Guests6
Bedrooms3
Bathroom1
Wonderful 5 / 5
$257 avg/night
3 beds
1 Bathroom
Guests 6
20 reviews
Ideal Location, Freshly Renovated, Sleeps 6; Check for Date...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$357 avg/night
3 beds
2 Bathrooms
Guests 8
9 reviews
Designers Own Year-Round Hudson Valley Getaway Cottage
Guests5
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$195 avg/night
2 beds
2 Bathrooms
Guests 5
28 reviews
Stunning Mountain Views Atop Blueberry Hill w/ 40 Private Acres
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.6 / 5
$240 avg/night
3 beds
2 Bathrooms
Guests 6
16 reviews
Enjoy Relaxing Organic Living in the Heart of the Berkshires!
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$243 avg/night
3 beds
2 Bathrooms
Guests 8
38 reviews
Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms
Guests8
Bedrooms4
Bathrooms2
Wonderful 4.3 / 5
$421 avg/night
4 beds
2 Bathrooms
Guests 8
9 reviews
Romantic Victorian Home
Guests6
Bedrooms2
Bathrooms3
Wonderful 5 / 5
$225 avg/night
2 beds
3 Bathrooms
Guests 6
16 reviews
Lovingly restored Victorian in Lee's Historic District
Guests12
Bedrooms5
Bathrooms5
Wonderful 4.8 / 5
$286 avg/night
5 beds
5 Bathrooms
Guests 12
32 reviews
Newly renovated 4 bedroom lakefront house in The Berkshires.
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$532 avg/night
4 beds
2 Bathrooms
Guests 10
7 reviews
Secluded Luxury, Perfectly Situated Between Tanglewood And...
Guests15
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$800 avg/night
5 beds
3 Bathrooms
Guests 15
28 reviews
Rare setting overlooking river - West Stockbridge Dream
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 8
24 reviews
Paradise Found in Up State New York Secluded, Beautiful, Private...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$363 avg/night
2 beds
1 Bathroom
Guests 6
14 reviews
Grey House-Hudson Valley/Berkshires
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 8
17 reviews
Newly Renovated Colonial on the River! Ready for Guests!
Guests5
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$241 avg/night
3 beds
2 Bathrooms
Guests 5
25 reviews
Quiet Get Away on the Lake!
Guests6
Bedrooms3
Bathroom1
Wonderful 4.9 / 5
$189 avg/night
3 beds
1 Bathroom
Guests 6
8 reviews
Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 8
7 reviews
Luxury Lakefront Lodge on 5 acre penninsula. Wi-Fi, Beach, Boats...
Guests16
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$329 avg/night
5 beds
3 Bathrooms
Guests 16
119 reviews
Blissful Beauty Near the Berkshires: 100+ Acres of Quiet in...
Guests6
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$239 avg/night
3 beds
3 Bathrooms
Guests 6
2 reviews

Chatham, NY, USA Vacation Rentals

Modern Cozy Wooded Retreat On 30 Private Acres

Spectacular all season well equipped, private retreat with...

Designer's Home In Idylic Country Setting, Near Hudson, Chatham...

Modern and cozy, nestled on a private perch above Chatham village.

Quiet Country Living

Peace, Quiet and close to The Berkshires and Hudson

Breathtaking Views of the Berkshires & Catskills, Gorgeous Newl...

Secluded Woodland Retreat - Berkshires, Hudson Valley

Chatham Village Hideaway

Country Estate-Year Round Resort - Pool and Hot tub

Two Ponds: Unique, Contemporary Compound with Magical Views in...

Spectacular River Views-Luxury Chalet w/ Indoor Pool & Spa on 23...

The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and...

Idyllic Berkshire Get Away: Balance of relaxation and convenience

Minutes from downtown Great Barrington, Convenient location

Stockbridge! 1/2 mile from Red Lion inn. Great Barrington, Lenox...

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town...

Cultural Playground of the East 2+ bed Cottage, 5 mins walk to the...

Family and Dog Friendly Retreat from the City ! (insta/fb...

Quiet Renovated Barn

A Small Oasis in the Heart of Lenox

Camp Kinderhook Lake House

Cozy Modern Berkshires Rental (mins From Lenox, Kripalu...

Chic Berkshire Carriage House

The Red Cottage on Copake Lake - A Stylishly Updated Home

Romantic Retreat Overlooking Lake

General Williams Estate House Lenox/Stockbridge

Beautiful Berkshire Cabin Close to All Attractions and Beach

Lovely Catskill Views, Close to Hudson, 5 minutes from Lake...

Luxury Living at the Lake

Sunny, Large, Home with beautiful gardens on pond. Walking...

Nature Lover's Paradise close to everything the Berkshires has to...

Restored 1780 Cottage Nestled In The Pastures Of Kinderhook Farm

Ideal Location, Freshly Renovated, Sleeps 6; Check for Date...

Designers Own Year-Round Hudson Valley Getaway Cottage

Stunning Mountain Views Atop Blueberry Hill w/ 40 Private Acres

Enjoy Relaxing Organic Living in the Heart of the Berkshires!

Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms

Romantic Victorian Home

Lovingly restored Victorian in Lee's Historic District

Newly renovated 4 bedroom lakefront house in The Berkshires.

Secluded Luxury, Perfectly Situated Between Tanglewood And...

Rare setting overlooking river - West Stockbridge Dream

Paradise Found in Up State New York Secluded, Beautiful, Private...

Grey House-Hudson Valley/Berkshires

Newly Renovated Colonial on the River! Ready for Guests!

Quiet Get Away on the Lake!

Berkshires, Ma. Close to Tanglewood, Jacob's PIllow, Berkshire...

Luxury Lakefront Lodge on 5 acre penninsula. Wi-Fi, Beach, Boats...

Blissful Beauty Near the Berkshires: 100+ Acres of Quiet in...