Chatham Vacation Rentals
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Distinctive Features
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5 mi
44 rentals in Chatham.
Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Spacious Serviced Apartment above Chatham Staple
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
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Home Sweet Home in a Best Place to Live Locale
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Cozy Chatham Retreat
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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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Nordic Cabin: your summertime haven
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous large renovated historic home on 10 acres with pool
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
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La Petite Maison, Chatham, NY
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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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
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Award-winning architectural gem, 17 acres, swimming pond, sited in state forest
Rental Home
4 bedrooms
6 bathrooms
Sleeps 4
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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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The following properties within 20 miles of Chatham match all your filters:
Hennett Road Hideaway
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
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Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!
Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Birds’ Nest Bungalow
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated Cabin in the Country
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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Ghent Getaway, Minutes from Hudson
Condo/Apartment
1 bedroom
0 bathrooms
Sleeps 3
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Suite 5 - Quiet and private accommodations in a country setting.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Suite 1 - Quiet and private accommodations in a country setting.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Suite 3 - Quiet and private accommodations in a country setting.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Suite 4 - Quiet and private accommodations in a country setting.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Martin Van Buren lake cottage 1
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Suite 2 - Quiet and private accommodations in a country setting.
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
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Martin Van Buren lake Cottage 2
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Welcome to the Red Bridge Cottage!
Rental Home
2 bedrooms
1 bathroom
Sleeps 2
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Cozy apartment overlooking our small farm. Family Friendly.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
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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 5
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Cute little ranch in the country
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
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Remodeled historic home w/backyard, steps to farmer's market, coffee, food, bars
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
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Welcome to WIndswept Acres in the Berkshire Mts!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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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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Evergreen House
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Family-Friendly Home
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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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19th Century Farm House on 300 Acre Farm
Rental Home
4 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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Secluded House with Picturesque Views in Historic Old Chatham, NY
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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A Country Retreat with Pool and Spacious Grounds
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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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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Country Estate Outside Hudson - Heated Pool Open on Mother's Day Weekend
Rental Home
6 bedrooms
4 bathrooms
Sleeps 14
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Spectacular All Seasons Retreat with Amazing Views
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
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Hillsdale Mountain View Estate on 7 Private Acres
Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
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Showing results 1-44 of 44
Frequently Asked Questions about Chatham
- Yes, here are some popular vacation rentals in Chatham that have a pool:
- Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
- Spacious Serviced Apartment above Chatham Staple
- Home Sweet Home in a Best Place to Live Locale
- Yes, here are some popular vacation rentals in Chatham that have internet access:
- Charming 1871 farmhouse retreat, wooded views in the historic village of Chatham
- Spacious Serviced Apartment above Chatham Staple
- Home Sweet Home in a Best Place to Live Locale
- The best pet friendly rentals in Chatham are:
- Cozy Chatham Retreat
- Nordic Cabin: your summertime haven
- Gorgeous large renovated historic home on 10 acres with pool
- Some of the most popular kid friendly rentals in Chatham are:
- Cozy Chatham Retreat
- 2,000 sq ft loft located "downtown" with access to dining..shops...movie theater
- Nordic Cabin: your summertime haven