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Compare 554 Vacation Homes in Annandale-on-Hudson with updated reviews, rates, and availability.

The Farm at Hyde Park
9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AED 694
AED 1,357 total
includes taxes & fees
14 Nov - 15 Nov
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (33)
"Loved the house. Pictures don’t do it justice. We had a few issues and the property manager was super responsive and had everything corrected. Would stay there again. "
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Bright, historic Woodstock home close to town
9.8 out of 10, Exceptional, (6)
"We loved the historic nature of the property. It is in a beautiful setting, just a short walk from downtown Woodstock. Cheryl was very responsive and helpful. Wish we had more time to enjoy the outdoor space!"
Bright, historic Woodstock home close to town
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
10.0 out of 10, Exceptional, (6)
"My family stayed here while visiting our daughter for parents weekend at Bard College. We have stayed in a number of rentals in the area over the past few years, and this is by far the best! It was perfect in every way: spacious, very clean and comfortable, everything worked well and the hosts were super responsive and kind. We will absolutely want to stay here again! "
‘A Gathering Den’ 3-bedrm house. Central to Belleayre, Hunter and Windham slopes
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Esopus Creek modern Tiny house Retreat!
9.6 out of 10, Exceptional, (17)
"A great spot close to Woodstock ny"
The price is AED 569
AED 830 total
includes taxes & fees
14 Nov - 15 Nov
Esopus Creek modern Tiny house Retreat!
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is AED 1,402
AED 1,560 total
includes taxes & fees
14 Nov - 15 Nov
Hudson River Way by Woodstock Way Hotel
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
10.0 out of 10, Exceptional, (9)
"What a special place. The overlook is gorgeous and the entire home was so relaxing. Perfect stay. "
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
9.8 out of 10, Exceptional, (19)
"Really love the mountains and fall leaves and lots to do and see in the area, unlike some resort towns. The accommodations were very nice, thank you! "
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (25)
"Perfect house and perfect location. Look forward to this trip yearly. Stephen makes everything easy and is always available. Great escape and property! "
5-Star New Barn Home - Music Studio, Views & Hot Tub
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (119)
"Girls weekend! Three 49 year old college roommates meeting up for a quick weekend of laughs. Best time. The house is adorable, comfortable, cozy rustic charm but also totally modern. Enjoyed Tinker Street, dinners out and a short hike. Highly recommend."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
4-bedrooms with gym+spa access steps from Garlic Festival
9.4 out of 10, Exceptional, (16)
"We were happy to see there was a full sized kitchen beautifully renovated with a back door to the nice back yard in addition to the wonderful bedroom accommodations. Lots of nice amenities plus antique furnishings but updated baths, just lovely. My only suggestions is more pillows."
The price is AED 551
AED 841 total
includes taxes & fees
1 Dec - 2 Dec
4-bedrooms with gym+spa access steps from Garlic Festival
Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
9.2 out of 10, Wonderful, (65)
"We had a girls weekend at this lovely farm house. the bedrooms were great, Jacuzzi great, central kitchen room is spacious - we lived in that room. Fresh eggs every morning were icing on the cake. "
Majestic Oasis in Rhinebeck w/ Hot Tub, Pool, Lake, & Fire Pit
Stunning Modern Barn minutes from Woodstock 21N-195
10.0 out of 10, Exceptional, (38)
"Property was wonderful for a fall getaway. Everything was clean and organized. Labels and clear directions for the lights and heating. Enjoyed slow mornings with a cup of tea, sitting in the sun on the porch. Days spent hiking in the area - there are plenty of hikes within a half hour of the house and a rail trail within 10 min if you’re looking for something easy. Evenings reading on the comfy couches and soaking in the hot tub under the stars. I would recommend staying here to anyone who wants...
Stunning Modern Barn minutes from Woodstock 21N-195
Modern-Chic Athens Home - Fish, Ski & Swim!
10.0 out of 10, Exceptional, (14)
"Our group of 12 had a great stay at the house. There was plenty of room for us all with the spacious bedrooms and 2 living room areas. We had 2 kids use the floor mattresses which worked well for them. The house was clean, kitchen well stocked, grill was easy to use, very close walk to the pool and beach areas. Lastly, the owner Alex was very easy to communicate with and answered questions right away. Highly recommend this house!"
Modern-Chic Athens Home - Fish, Ski & Swim!
Steps to Garlic Festival Saugerties home with gym+spa access.
9.4 out of 10, Exceptional, (10)
"Super convenient to the show grounds which was the #1 draw for the house. We didn't realize there was no washer dryer - but not the end of the world with laundry service close by. House manager was great - very responsive. "
Steps to Garlic Festival Saugerties home with gym+spa access.
Cleo’s Cabin: Private Retreat with Fenced Dog Run
9.0 out of 10, Wonderful, (9)
"We really love this property and the communication with our hosts was seamless. Our group all appreciated the cozy living room with the warm stove. And the beds are beyond comfortable. "
Cleo’s Cabin: Private Retreat with Fenced Dog Run
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Annandale-on-Hudson

The Farm at Hyde Park
9.8 out of 10, Exceptional, (63)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (21)
"Kevin was great with being flexible about check in time! My sister and I didn't get in until past 9pm and it was no problem! And it's a plus that he's very pet friendly as I had my dog and cat with me!"
The price is AED 364
AED 584 total
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream
Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (223)
"The property was beautiful and secluded providing the peaceful getaway from the city that we needed. The host is also incredibly friendly and provided the easiest check in/out process I’ve seen. Loved Woodstock! "
The price is AED 657
AED 1,179 total
includes taxes & fees
27 Nov - 28 Nov
Streamside Cottage Half Mile to Town of Woodstock
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.