Holiday Rentals in Chatham
Holiday Rentals in Chatham
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50 rentals in Chatham.
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Beautiful & Private w/ Heated Pool, Jacuzzi, Pond! Summer weeks available!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Farm House on 460 Acre Working Farm
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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La Petite Maison, Chatham, NY
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Secluded Cabin in the Berkshires
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Relax in the Country - Peace, quiet and family friendly
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Upstate Cabin: A secluded getaway in the woods
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Scandi-style modern cabin in Chatham
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Two Ponds: Modern Compound with Magical Views in Columbia County
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Serenity on Stony Kill: 3BR Creek Front Cottage
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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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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Award-winning architectural gem, 17 acres, swimming pond, sited in state forest
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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The Honeydew: Cozy*hot tub*fire pit*walk to dinner
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious Serviced Apartment above Chatham Staple
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Berkshire Country Estate: Enjoy beautiful 60 acre estate for a special vacation!
Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Spectacular All Seasons Retreat with Amazing Views
Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Designer Home with Panoramic Views near Hudson
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Pond View Cottage in Old Chatham WEEKLY & MONTHLY DISCOUNTS OFFERED!!!!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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A Beautiful Retreat In a Stunning Home and Landscaped Lawns
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
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Beautifully Renovated Exposed Beam Bungalow
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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18th Century Hilltop Home Nestled in Bucolic Oasis
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Hudson 2 bedroom bungalow apartment at the Wilbur Estate
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Hudson Old Chatham Loft
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Secluded House with Picturesque Views in Historic Old Chatham, NY
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley Chalet with hot tub/nearby skiing
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy apartment overlooking our small farm. Family Friendly.
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Secluded Family-Friendly Home
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A 200 year old center hall colonial between the Berkshires and the Hudson River
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - WATER + WOODS
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Welcome to the Red Bridge Cottage!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Cozy Wooded Retreat
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to WIndswept Acres in the Berkshire Mts!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Samuel Wilbur Estate ~ Established 1810
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley Berkshires Cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Home Sweet Home in a Best Place to Live Locale
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Incredible Estate w/ Pool, Pond, Barn, Trails & More! RESERVE for SUMMER NOW!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Berkshires Hudson Valley View Cottage - Private & Quiet
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chalet near 4 ski resorts with hot tub
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Ghent Getaway, Minutes from Hudson
Condo/Apartment
1 bedroom
0 bathrooms
Sleeps 3
Match: Sleeps
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Tentrr Signature Site - WATER + WOODS
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful 6+ Bedroom Farmhouse On 460 Acre Working Farm
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Cute little ranch in the country
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Martin Van Buren lake cottage 1
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Country Retreat with Pool and Spacious Grounds
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Suite 3 - Quiet and private accommodations in a country setting.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Suite 5 - Quiet and private accommodations in a country setting.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Martin Van Buren lake Cottage 2
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Bucolic country home near local villages and Hudson Valley happenings
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy Ski Getaways at Beautiful, Special 5 Star Estate! Free Ski Pass w/Booking!
Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Showing results 1-50 of 50
Frequently Asked Questions about Chatham
- Yes, here are some popular holiday rentals in Chatham that have a pool:
- Two Ponds: Modern Compound with Magical Views in Columbia County
- Relax in the Country - Peace, quiet and family friendly
- Cozy Secluded Cabin in the Berkshires
- Yes, here are some popular holiday rentals in Chatham that have internet access:
- Two Ponds: Modern Compound with Magical Views in Columbia County
- Relax in the Country - Peace, quiet and family friendly
- Cozy Secluded Cabin in the Berkshires
- Some of the most popular kid friendly rentals in Chatham are:
- Two Ponds: Modern Compound with Magical Views in Columbia County
- Relax in the Country - Peace, quiet and family friendly
- Cozy Secluded Cabin in the Berkshires