East Chatham Vacation Rentals
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Bedrooms
Bathrooms
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Suitability
Property type
Distinctive Features
Distance from
5 mi
50 rentals in East Chatham.
Newly Renovated Cabin in the Country
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Welcome to WIndswept Acres in the Berkshire Mts!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded Family-Friendly Home
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Hudson Valley Chalet with hot tub minutes to Chatham
Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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Dream getaway - mtn views, ski, pool, deck, nearby lake, work from home setups
Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
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Birds’ Nest Bungalow
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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Historic home in country hamlet. 30 min to Tanglewood, Hudson, Berkshires + more
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Chalet near 4 ski resorts with hot tub
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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The following properties within 20 miles of East Chatham match all your filters:
Charming Guest Suite
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Hudson Valley Berkshires Cottage
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!
Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
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Hudson Old Chatham Loft
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Round House
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Beautifully Renovated Exposed Beam Bungalow
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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The Upstate Cabin: A secluded getaway in the woods
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Welcome to the Red Bridge Cottage!
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Spacious Serviced Apartment above Chatham Staple
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
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The Hudson 2 bedroom bungalow apartment at the Wilbur Estate
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Berkshires Hudson Valley View Cottage - Private & Quiet
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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A 200 year old center hall colonial between the Berkshires and the Hudson River
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Hudson River Valley/Berkshires Rural Retreat
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
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2,000 sq ft loft located "downtown" with access to dining..shops...movie theater
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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The Home in Malden Bridge, Columbia County, New York
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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Nordic Cabin: your summertime haven
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Charming 1800s home with fenced in yard and bucolic farm views !
Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
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La Petite Maison, Chatham, NY
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Charming Farm House on 460 Acre Working Farm
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Serenity on Stony Kill: 3BR Creek Front Cottage
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Your Dream House: Pine Log Chalet, Sauna, Outdoor Pool
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Berkshire Rural Retreat
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Secluded House with Picturesque Views in Historic Old Chatham, NY
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Samuel Wilbur Estate ~ Established 1810
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Private Tennis court, hot tub & pool Berkshires 13 acre Estate 4 bedrooms
Rental Home
4 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Estate w/ Arcade, Library, Gym, Trails etc. Ask about Private Chef!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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August Summer weeks available! Pool, Jacuzzi, Pond, Private Chef & More!
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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Berkshires Lake House With Private Dock and Chefs Kitche
Rental Home
6 bedrooms
3 bathrooms
Sleeps 12
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Modern home w/Pool and Views near Chatham and Hudson
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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Spectacular All Seasons Retreat with Amazing Views
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm
Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
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Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!
Rental Home
9 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Hand Hollow Haven - A Home Away From Home
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Cottage in the Woods
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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One-of-a-Kind Breathtaking Berkshire Retreat
Rental Home
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Your Dream House: Log Chalet, Sauna, Close To Skiing
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Frequently Asked Questions about East Chatham
- Yes, here are some popular vacation rentals in East Chatham that have a pool:
- Newly Renovated Cabin in the Country
- Welcome to WIndswept Acres in the Berkshire Mts!
- Secluded Family-Friendly Home
- Yes, here are some popular vacation rentals in East Chatham that have internet access:
- Newly Renovated Cabin in the Country
- Welcome to WIndswept Acres in the Berkshire Mts!
- Secluded Family-Friendly Home
- Some of the most popular kid friendly rentals in East Chatham are:
- Newly Renovated Cabin in the Country
- Welcome to WIndswept Acres in the Berkshire Mts!
- Secluded Family-Friendly Home