Holiday rentals near Dutchess County Fairgrounds
We found 1,115 holiday rentals — enter your dates for availability
If you are looking to stay near Dutchess County Fairgrounds, take a look at holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, which might include Wi-Fi and a fireplace. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Dutchess County Fairgrounds
Showing deals for:19 Sept - 26 Sept
Image gallery for Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
1010 out of 10 rating
Exceptional
(40 reviews)
Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views
High Falls, NY
8% off
Price is AU$14,304
AU$14,304
AU$2,043 per night
includes taxes & fees
Image gallery for Pool is open & heated! Country lux w/ Priv hot tub! Explore the Carskills!
1010 out of 10 rating
Exceptional
(181 reviews)
Pool is open & heated! Country lux w/ Priv hot tub! Explore the Carskills!
Hurley, NY
8% off
Price is AU$4,344
AU$4,344
AU$621 per night
includes taxes & fees
Image gallery for Charming rustic home in the Hudson Valley. New Hot Tub! Close to Hunter/Windham
1010 out of 10 rating
Exceptional
(5 reviews)
Charming rustic home in the Hudson Valley. New Hot Tub! Close to Hunter/Windham
Saugerties, NY
12% off
Price is AU$7,004
AU$7,004
AU$1,001 per night
includes taxes & fees
Image gallery for Rustic Quarry Luxury with Private Lake
1010 out of 10 rating
Exceptional
(6 reviews)
Rustic Quarry Luxury with Private Lake
Saugerties, NY
17% off
Price is AU$13,720
AU$13,720
AU$1,960 per night
includes taxes & fees
Image gallery for Beautiful Saugerties Rental, close to HITS, Hiking, Festivals, Skiing
1010 out of 10 rating
Exceptional
(24 reviews)
Beautiful Saugerties Rental, close to HITS, Hiking, Festivals, Skiing
Saugerties, NY
8% off
Price is AU$9,961
AU$9,961
AU$1,423 per night
includes taxes & fees
Image gallery for Ashokan ArtHaus, Private Hot Tub, Wags Welcome!
1010 out of 10 rating
Exceptional
(7 reviews)
Ashokan ArtHaus, Private Hot Tub, Wags Welcome!
West Shokan, NY
20% off
Price is AU$3,558
AU$3,558
AU$508 per night
includes taxes & fees
Image gallery for Modern Hudson Valley Creekside Retreat + Hot Tub!
1010 out of 10 rating
Exceptional
(12 reviews)
Modern Hudson Valley Creekside Retreat + Hot Tub!
Hyde Park, NY
16% off
Price is AU$5,805
AU$5,805
AU$829 per night
includes taxes & fees
Image gallery for Secluded House with hot tub at base of Shawangunk Ridge
1010 out of 10 rating
Exceptional
(8 reviews)
Secluded House with hot tub at base of Shawangunk Ridge
New Paltz, NY
8% off
Price is AU$8,240
AU$8,240
AU$1,177 per night
includes taxes & fees
Image gallery for Stunning Modern Barn minutes from Woodstock 21N-195
1010 out of 10 rating
Exceptional
(41 reviews)
Stunning Modern Barn minutes from Woodstock 21N-195
Mount Tremper, NY
8% off
Price is AU$5,978
AU$5,978
AU$854 per night
includes taxes & fees
Image gallery for Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
1010 out of 10 rating
Exceptional
(5 reviews)
Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
Ancram, NY
8% off
Price is AU$3,981
AU$3,981
AU$569 per night
includes taxes & fees
Image gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
1010 out of 10 rating
Exceptional
(68 reviews)
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
Bearsville, NY
8% off
Price is AU$8,541
AU$8,541
AU$1,220 per night
includes taxes & fees
Image gallery for Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
1010 out of 10 rating
Exceptional
(93 reviews)
Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
Saugerties, NY
8% off
Price is AU$2,353
AU$2,353
AU$336 per night
includes taxes & fees
Image gallery for In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,
9.69.6 out of 10 rating
Exceptional
(43 reviews)
In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,
Woodstock, NY
16% off
Price is AU$2,973
AU$2,973
AU$425 per night
includes taxes & fees
Image gallery for Mid-Century Modern Gem, Heated Pool, 1 Mile from Town
1010 out of 10 rating
Exceptional
(33 reviews)
Mid-Century Modern Gem, Heated Pool, 1 Mile from Town
Woodstock, NY
8% off
Price is AU$7,128
AU$7,128
AU$1,018 per night
includes taxes & fees
Image gallery for Pet Friendly Cabin Doh-Ray up @ 1500 ft
1010 out of 10 rating
Exceptional
(62 reviews)
Pet Friendly Cabin Doh-Ray up @ 1500 ft
Woodstock, NY
8% off
Price is AU$3,672
AU$3,672
AU$525 per night
includes taxes & fees
Image gallery for Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
Ancram, NY
12% off
Price is AU$6,787
AU$6,787
AU$970 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(6 reviews)
Taghkanic Glass House
Hudson, NY
9% off
Price is AU$50,998
AU$50,998
AU$7,285 per night
includes taxes & fees
Image gallery for NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
1010 out of 10 rating
Exceptional
(127 reviews)
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Ulster Park, NY
8% off
Price is AU$12,947
AU$12,947
AU$1,850 per night
includes taxes & fees
Image gallery for Modern Cabin In the Woods
1010 out of 10 rating
Exceptional
(13 reviews)
Modern Cabin In the Woods
Kingston, NY
11% off
Price is AU$5,394
AU$5,394
AU$771 per night
includes taxes & fees
Image gallery for UNIQUE! 40 Pvt. Ac. Fireplace, Grill, Enclosed Heated Pool & Hot Tub
9.89.8 out of 10 rating
Exceptional
(17 reviews)
UNIQUE! 40 Pvt. Ac. Fireplace, Grill, Enclosed Heated Pool & Hot Tub
Saugerties, NY
6% off
Price is AU$8,925
AU$8,925
AU$1,275 per night
includes taxes & fees
Image gallery for Private oasis, ideal for families! Hot tub always open! Heated pool open in May!
1010 out of 10 rating
Exceptional
(39 reviews)
Private oasis, ideal for families! Hot tub always open! Heated pool open in May!
Woodstock, NY
16% off
Price is AU$6,602
AU$6,602
AU$943 per night
includes taxes & fees
Image gallery for Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
9.49.4 out of 10 rating
Exceptional
(68 reviews)
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Pine Plains, NY
8% off
Price is AU$2,895
AU$2,895
AU$414 per night
includes taxes & fees
Image gallery for Hilltop Home on 10 acres w/ hot tub, fire-pit + solar
1010 out of 10 rating
Exceptional
(13 reviews)
Hilltop Home on 10 acres w/ hot tub, fire-pit + solar
Pine Plains, NY
8% off
Price is AU$5,467
AU$5,467
AU$781 per night
includes taxes & fees
Image gallery for Luxury in Saugerties - Hot tub - Theater - Firepit
1010 out of 10 rating
Exceptional
(6 reviews)
Luxury in Saugerties - Hot tub - Theater - Firepit
Saugerties, NY
8% off
Price is AU$5,430
AU$5,430
AU$776 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Dutchess County Fairgrounds
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Hamptons on the Hudson in South Saugerties
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
197 reviews(197 reviews)
The HITS House. Golf cart, bicycle, or walk to the show. Heated saltwater pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Sleeps 2 · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Charming Stone Chalet in Wooded Surroundings with Heated Pool Spring to Fall.
Sleeps 7 · 4 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
165 reviews(165 reviews)
Top rated rentals - Dutchess County Fairgrounds
Family getaway
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Clean, comfortable and cozy
1010 out of 10
Exceptionalexceptional
166 reviews(166 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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value