East Chatham Holiday Rentals
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44 rentals in East Chatham.
Newly Renovated Cabin in the Country
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Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
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Welcome to WIndswept Acres in the Berkshire Mts!
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Hudson Valley Chalet
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Dream getaway - mtn views, ski, pool, BBQ, Firepit, Kid friendly, Lakes, WFH
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Luxury Barn Retreat — All-Season Escape Awaits!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Private Homestead - Cozy Comforts & Scenic Views!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Red Rock Summit: Mtn Escape w/ Pool, Pond + Views
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Secluded Family-Friendly Home
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Birds’ Nest Bungalow
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10 Acre Country Estate with Pool, Hot Tub & Views!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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The following properties within 20 miles of East Chatham match all your filters:
Cozy Cottage in the Woods
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Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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One-of-a-Kind Breathtaking Berkshire Retreat
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Berkshire Rural Retreat
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Secluded House with Picturesque Views in Historic Old Chatham, NY
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Private estate with Hot Tub, Tennis Court & Pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Amazing, Private Estate for up to 8 guests! Pool, Pond, Gym, Arcade, Barn & More
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Berkshires Lake House With Private Dock, gunite pool, and Chefs Kitchen
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Four season lake side oasis in the berkshirkes
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Mountain View Retreat in Hudson Valley near Berkshire Attractions
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Charming 1800s home with fenced in yard and bucolic farm views !
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Plan your Berkshires by the lake
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2,000 sq ft loft located "downtown" with access to dining..shops...movie
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Hilltop House
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Welcome to the Red Bridge Cottage!
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A charming private 3-bedroom country house with scenic views and sprawling lawn
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular All Seasons Retreat with Amazing Views
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Hudson River Valley/Berkshires Rural Retreat
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Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!
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Sugar Shack - 300 square feet of pure sweetness.
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Harmony House in Hudson Valley- Pet Friendly
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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SRC-Hudson Valley/Berkshires Cultural Corridor
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Black Friday Sale - Secluded Mountain and Lake View in Canaan, NY
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A 200 year old center hall colonial between the Berkshires and the Hudson River
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Renovated Country Retreat, 11+ Acres by Evergreen Home
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2
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Spacious Serviced Apartment above Chatham Staple
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9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
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Elegant Upstate Sanctuary on 20 Acres
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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HunnyHAUS: Deluxe TINY*private spa*walk to town
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Renovated Chatham Home ~ Half Mi to Downtown!
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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BLUSH: Boutique TINY home*private spa*walk to town
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Showing results 1-44 of 44
Frequently Asked Questions about East Chatham
- Yes, here are some popular holiday rentals in East Chatham that have a pool:
- Newly Renovated Cabin in the Country
- Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
- Welcome to WIndswept Acres in the Berkshire Mts!
- Yes, here are some popular holiday rentals in East Chatham that have internet access:
- Newly Renovated Cabin in the Country
- Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
- Welcome to WIndswept Acres in the Berkshire Mts!
- Some of the most popular kid friendly rentals in East Chatham are:
- Newly Renovated Cabin in the Country
- Comfortable and charming 3 Bedroom Retreat-Enjoy Hudson Valley & Berkshires
- Welcome to WIndswept Acres in the Berkshire Mts!
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