Holiday rentals near Hudson Chatham Winery
We found 974 holiday rentals — enter your dates for availability
Find the perfect private holiday rental that's close to Hudson Chatham Winery. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Hudson Chatham Winery
Showing deals for:7 Nov - 14 Nov
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
15% off
Price is £3,841
£3,841
£549 per night
includes taxes & fees
Image gallery for Modern Glass House designed by renowned architect Thomas Phifer
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Modern Glass House designed by renowned architect Thomas Phifer
Hudson, NY
8% off
Price is £2,511
£2,511
£359 per night
includes taxes & fees
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, NY
11% off
Price is £1,755
£1,755
£251 per night
includes taxes & fees
Image gallery for Charming cottage with lake access, wood burning fire place, and WiFi
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Charming cottage with lake access, wood burning fire place, and WiFi
Elizaville, NY
12% off
Price is £1,082
£1,082
£155 per night
includes taxes & fees
Image gallery for Perfect home for a getaway from NYC
1010 out of 10 rating
Exceptional
(12 reviews)
Perfect home for a getaway from NYC
Athens, NY
8% off
Price is £3,098
£3,098
£443 per night
includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is £6,709
£6,709
£958 per night
includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
8% off
Price is £7,518
£7,518
£1,074 per night
includes taxes & fees
Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
1010 out of 10 rating
Exceptional
(24 reviews)
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Ghent, NY
10% off
Price is £4,894
£4,894
£699 per night
includes taxes & fees
Image gallery for Cozy Red Cottage on Robinson Pond nestled between the Berkshires and Catskills.
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy Red Cottage on Robinson Pond nestled between the Berkshires and Catskills.
Copake, NY
15% off
Price is £1,551
£1,551
£222 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is £3,432
£3,432
£490 per night
includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
8% off
Price is £1,888
£1,888
£270 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
7% off
Price is £1,312
£1,312
£187 per night
includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
30% off
Price is £41,992
£41,992
£5,999 per night
includes taxes & fees
Image gallery for Casa Bartolo, Your Oasis on the Hudson!
1010 out of 10 rating
Exceptional
(29 reviews)
Casa Bartolo, Your Oasis on the Hudson!
Hudson, NY
12% off
Price is £1,767
£1,767
£252 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(27 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
7% off
Price is £6,237
£6,237
£891 per night
includes taxes & fees
Image gallery for "Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
1010 out of 10 rating
Exceptional
(6 reviews)
"Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
Castleton-on-Hudson, NY
8% off
Price is £4,469
£4,469
£638 per night
includes taxes & fees
Image gallery for Country living close to the capital region 100 acres of nature to explore
1010 out of 10 rating
Exceptional
(5 reviews)
Country living close to the capital region 100 acres of nature to explore
Nassau, NY
7% off
Price is £1,818
£1,818
£260 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(53 reviews)
Stunning Renovated Victorian
Great Barrington, MA
15% off
Price is £5,729
£5,729
£818 per night
includes taxes & fees
Image gallery for Heaven on Earth - Hudson Riverfront Home
1010 out of 10 rating
Exceptional
(16 reviews)
Heaven on Earth - Hudson Riverfront Home
Catskill, NY
8% off
Price is £2,890
£2,890
£413 per night
includes taxes & fees
Image gallery for OMG! 3 Houses,10 Acres, Pickleball, Pool, Hot Tub,10 miles to Hunter Mountain
1010 out of 10 rating
Exceptional
(5 reviews)
OMG! 3 Houses,10 Acres, Pickleball, Pool, Hot Tub,10 miles to Hunter Mountain
Catskill, NY
8% off
Price is £7,500
£7,500
£1,071 per night
includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(24 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is £2,995
£2,995
£428 per night
includes taxes & fees
Image gallery for The Hideaway: Berkshire Home - Village of Egremont
9.69.6 out of 10 rating
Exceptional
(25 reviews)
The Hideaway: Berkshire Home - Village of Egremont
Great Barrington, MA
16% off
Price is £1,613
£1,613
£230 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(7 reviews)
Taghkanic Glass House
Hudson, NY
9% off
Price is £25,325
£25,325
£3,618 per night
includes taxes & fees
Image gallery for Fun Getaway Lakehouse in the Hudson Valley
1010 out of 10 rating
Exceptional
(15 reviews)
Fun Getaway Lakehouse in the Hudson Valley
Craryville, NY
12% off
Price is £2,504
£2,504
£358 per night
includes taxes & fees
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Find the best place to stay - Hudson Chatham Winery
Charming Cottage in Private Lake Community (Pet-Friendly!)
Sleeps 7 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Spacious 3-bedroom apartment in Catskill village - walkable to area attractions
Sleeps 6 · 3 bedrooms · 1 bathroom
Private luxury with heated pool less than 10 min from downtown Great Barrington
Sleeps 8 · 3 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Olive Pit: Scenic Designer Retreat +Pool—Sleeps 12
Sleeps 12 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Beautifully Designed 4BR Home with Heated Pool and HotTub
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Hudson: Martin Van Buren 2 bedroom lake house cottage
Sleeps 4 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value