Holiday rentals near Dutchess County Fairgrounds
We found 1,118 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:3 Oct - 10 Oct
Image gallery for Farmette Roquette Hudson Valley
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Farmette Roquette Hudson Valley
Germantown, NY
8% off
Price is AU$7,719
AU$7,719
AU$1,103 per night
includes taxes & fees
Image gallery for Sunset Mountain Retreat - mins from Woodstock
1010 out of 10 rating
Exceptional
(20 reviews)
Sunset Mountain Retreat - mins from Woodstock
Mount Tremper, NY
11% off
Price is AU$6,432
AU$6,432
AU$919 per night
includes taxes & fees
Image gallery for Beautiful Village 2BR loaded with extras
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful Village 2BR loaded with extras
Saugerties, NY
16% off
Price is AU$3,497
AU$3,497
AU$500 per night
includes taxes & fees
Image gallery for Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
9.49.4 out of 10 rating
Exceptional
(67 reviews)
Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
Rhinebeck, NY
8% off
Price is AU$13,657
AU$13,657
AU$1,951 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$8,419
AU$8,419
AU$1,203 per night
includes taxes & fees
Image gallery for Tower Hill - Hilltop Country Retreat with Panoramic Views
1010 out of 10 rating
Exceptional
(15 reviews)
Tower Hill - Hilltop Country Retreat with Panoramic Views
Millbrook, NY
8% off
Price is AU$10,381
AU$10,381
AU$1,483 per night
includes taxes & fees
Image gallery for Cabin 85 - 2bd rooms w/ 2 lofty chic spaces
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Cabin 85 - 2bd rooms w/ 2 lofty chic spaces
Hurley, NY
12% off
Price is AU$2,959
AU$2,959
AU$423 per night
includes taxes & fees
Image gallery for Stunning Light-Filled Contemporary Home on 7 Acres
1010 out of 10 rating
Exceptional
(25 reviews)
Stunning Light-Filled Contemporary Home on 7 Acres
Salt Point, NY
22% off
Price is AU$5,400
AU$5,400
AU$771 per night
includes taxes & fees
Image gallery for Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
1010 out of 10 rating
Exceptional
(16 reviews)
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook, NY
8% off
Price is AU$3,489
AU$3,489
AU$498 per night
includes taxes & fees
Image gallery for The House In Highland- Secluded Retreat
1010 out of 10 rating
Exceptional
(6 reviews)
The House In Highland- Secluded Retreat
Highland, NY
8% off
Price is AU$7,384
AU$7,384
AU$1,055 per night
includes taxes & fees
Image gallery for Perfect Getaway - Luxury Cabin w/ Mtn View
1010 out of 10 rating
Exceptional
(11 reviews)
Perfect Getaway - Luxury Cabin w/ Mtn View
Germantown, NY
12% off
Price is AU$3,758
AU$3,758
AU$537 per night
includes taxes & fees
Image gallery for Stunning Custom Designer Home in the Catskills!
1010 out of 10 rating
Exceptional
(18 reviews)
Stunning Custom Designer Home in the Catskills!
Saugerties, NY
8% off
Price is AU$8,112
AU$8,112
AU$1,159 per night
includes taxes & fees
Image gallery for Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
1010 out of 10 rating
Exceptional
(6 reviews)
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
New Paltz, NY
8% off
Price is AU$8,337
AU$8,337
AU$1,191 per night
includes taxes & fees
Image gallery for Glamping in the woods, beautiful property one hour from NYC.
1010 out of 10 rating
Exceptional
(5 reviews)
Glamping in the woods, beautiful property one hour from NYC.
Pleasant Valley, NY
11% off
Price is AU$1,597
AU$1,597
AU$228 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$9,819
AU$9,819
AU$1,403 per night
includes taxes & fees
Image gallery for Higashi: New Paltz family home with King bed minutes to downtown
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Higashi: New Paltz family home with King bed minutes to downtown
New Paltz, NY
8% off
Price is AU$4,279
AU$4,279
AU$611 per night
includes taxes & fees
Image gallery for MODERN FARMHOUSE, Saugerties Woodstock, Deck, Fireplace, Fire Pit, WiFi, TV
1010 out of 10 rating
Exceptional
(52 reviews)
MODERN FARMHOUSE, Saugerties Woodstock, Deck, Fireplace, Fire Pit, WiFi, TV
Saugerties, NY
6% off
Price is AU$5,456
AU$5,456
AU$779 per night
includes taxes & fees
Image gallery for Cheerful Circa 1700 3 Bedroom Farmhouse
1010 out of 10 rating
Exceptional
(6 reviews)
Cheerful Circa 1700 3 Bedroom Farmhouse
Hyde Park, NY
30% off
Price is AU$4,645
AU$4,645
AU$664 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$9,057
AU$9,057
AU$1,294 per night
includes taxes & fees
Image gallery for COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!
9.89.8 out of 10 rating
Exceptional
(72 reviews)
COUNTRY HOME Fenced Backyard, 1 mi. to Town, Kids & Dogs OK!
Woodstock, NY
9% off
Price is AU$5,235
AU$5,235
AU$748 per night
includes taxes & fees
Image gallery for THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
9.89.8 out of 10 rating
Exceptional
(7 reviews)
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Saugerties, NY
9% off
Price is AU$3,998
AU$3,998
AU$571 per night
includes taxes & fees
Image gallery for Heated pool, outdoor deck, fire pit, basketball court, fireplaces, central air.
9.69.6 out of 10 rating
Exceptional
(34 reviews)
Heated pool, outdoor deck, fire pit, basketball court, fireplaces, central air.
Woodstock, NY
12% off
Price is AU$8,081
AU$8,081
AU$1,154 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
(183 reviews)
Pool is open & heated! Country lux w/ Priv hot tub! Explore the Carskills!
Hurley, NY
8% off
Price is AU$4,282
AU$4,282
AU$612 per night
includes taxes & fees
Image gallery for Sweet spot studio on village outskirts
1010 out of 10 rating
Exceptional
(27 reviews)
Sweet spot studio on village outskirts
New Paltz, NY
8% off
Price is AU$2,906
AU$2,906
AU$415 per night
includes taxes & fees
Find spaces that suit your style
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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
23 reviews(23 reviews)
The HITS House. Golf cart, bicycle, or walk to the show. Heated saltwater pool
Sleeps 10 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
26 reviews(26 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
198 reviews(198 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
166 reviews(166 reviews)
Peacock Garden Cottage, A Unique Upstate Find
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
12 reviews(12 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