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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 564 Vacation Homes in Annandale-on-Hudson with updated reviews, rates, and availability.

Quaint Cottage with Peloton Bike & Sauna near Skiing
Cozy Catskills cottage living room

Quaint Cottage with Peloton Bike & Sauna near Skiing

9.6 out of 10, Exceptional, (12)
"Once you connect to the wifi you can use your phone. The landlord as well as property manager are helpful and actually respond. Property is very peaceful!"
Quaint Cottage with Peloton Bike & Sauna near Skiing
The Tipsy Gypsy
Exterior

The Tipsy Gypsy

9.8 out of 10, Exceptional, (20)
"Great location. Very clean and cozy. Very nice people to work with. My kids loved it as well."
The price is SAR 844
SAR 1,703 total
includes taxes & fees
23 Feb - 24 Feb
The Tipsy Gypsy
Esopus Creek modern Tiny house Retreat!
Interior

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"Great little house for the holidays. We were looking for a place nearby or family where we could have our own space but still be close by. "
The price is SAR 581
SAR 843 total
includes taxes & fees
26 Feb - 27 Feb
Esopus Creek modern Tiny house Retreat!
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Living area

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

9.6 out of 10, Exceptional, (23)
"Beautiful place. Right across from Hunter mountain. We enjoyed our stay."
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY
View of the wood-burning stove, sectional sofa, kitchen and dining area

Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY

10.0 out of 10, Exceptional, (36)
"We rented this house for ourselves and our friends for our wedding weekend around the corner. It was the best decision, large group and we had plenty of places to sleep, the yard gave ample space for activities, the sound system kept us entertained, and the kitchen made hosting a large group a breeze. Yuri was amazing in making himself available and our stay memorable. Can’t wait to visit again!"
Luxurious & Enchanting Log House in Heart of Hudson Valley/Catskills, Upstate NY
Experience Woodstock charm while staying in a cozy cabin in the woods
Driveway and Entrance

Experience Woodstock charm while staying in a cozy cabin in the woods

9.8 out of 10, Exceptional, (23)
"Missy was a fantastic communicator from the beginning. Her place was perfect for two families of four. The house is well kept and the perfect distance from town, hiking, Opus 40 and much more. Highly recommend."
Experience Woodstock charm while staying in a cozy cabin in the woods
Charming cottage with lake access, wood burning fire place, and WiFi
Sun room with pull out sofa bed.

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles
Cozy on the Hudson River

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles
Hudson River Way by Woodstock Way Hotel
Exterior

Hudson River Way by Woodstock Way Hotel

5.0 star property
The price is SAR 1,171
SAR 1,364 total
includes taxes & fees
5 Mar - 6 Mar
Hudson River Way by Woodstock Way Hotel
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
The Hudson Valley is calling!

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Living area

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.4 out of 10, Exceptional, (23)
"This property is clean, updated and warm! We were up for a race at Catamount and this cottage was perfect for our weekend stay. The host, Robert, was quick to respond when contacted with a quick question and otherwise there were no issues. "
The price is SAR 731
SAR 1,409 total
includes taxes & fees
20 Feb - 21 Feb
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Always a great stay at this beautiful house!"
Beautiful new house 3/4 mile from Hunter Mountain
Amenity Packed Waterfront Retreat w/ Hot Tub & Wood Burning Stove!
Usable waterfront with kayaks and life vest provided!

Amenity Packed Waterfront Retreat w/ Hot Tub & Wood Burning Stove!

10.0 out of 10, Exceptional, (5)
"I rented this house for my bridal party to stay at the weekend of my wedding. This place was absolutely stunning. It was very cozy and had a fantastic view. The check in process and communicating with the hosts was so easy. Would love to go back there again at some point. "
Amenity Packed Waterfront Retreat w/ Hot Tub & Wood Burning Stove!
Catskills Country House with Hot Tub and Sauna Near Skiing
Living room space

Catskills Country House with Hot Tub and Sauna Near Skiing

9.6 out of 10, Exceptional, (10)
"Another great stay"
Catskills Country House with Hot Tub and Sauna Near Skiing
Winter Ski House with gym +spa access
Exterior

Winter Ski House with gym +spa access

9.6 out of 10, Exceptional, (13)
"We loved our stay for the holidays. Home is warm, inviting, and clean. Host was accommodating. Beds are comfy and the kitchen was big and modern. Will definitely be back! "
Winter Ski House with gym +spa access
NEW! Bright and Cheerful Historic Cottage in Woodstock
Living area

NEW! Bright and Cheerful Historic Cottage in Woodstock

10.0 out of 10, Exceptional, (1)
"My husband and I had a wonderful stay. Kristin was quick to respond, provided easy and accurate check in instructions, and even came by in the morning after a snowstorm to shovel the stairs and driveway. The house itself is so great! Pictured as is from the listing- clean, well stocked kitchen, eclectically and thoughtfully designed, and working fireplace with wood provided was definitely a plus. If you’re planning a trip to the Woodstock area, I would highly recommend Kristin’s place and we...
NEW! Bright and Cheerful Historic Cottage in Woodstock
Mountaintop Lookout with Hot Tub under the Stars - Ultimate Family Getaway!
Welcome to The Mountaintop Lookout. Inspired by Nature, crafted with Love

Mountaintop Lookout with Hot Tub under the Stars - Ultimate Family Getaway!

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay- 3 families with 6 adults and 3 kids. Clean and fun and great area- we hiked and went to hunter mountain!"
Mountaintop Lookout with Hot Tub under the Stars - Ultimate Family Getaway!
Kingston Crawfish Cottage Near Catskills!
Kingston Vacation Rental | Studio | 1BA | 400 Sq Ft | Small Step for Entry

Kingston Crawfish Cottage Near Catskills!

10.0 out of 10, Exceptional, (11)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!
New! Thoughtful and Cozy Craftsman Waiting for You! Walk to village center!
Exterior shot of the backyard

New! Thoughtful and Cozy Craftsman Waiting for You! Walk to village center!

10.0 out of 10, Exceptional, (3)
"Loved our little stay at this property. You can tell the space is well taken care of and extra stocked with little needs which is extra appreciated. Would highly recommend!"
New! Thoughtful and Cozy Craftsman Waiting for You! Walk to village center!
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

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is SAR 469
SAR 506 total
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Eastern Catskills
Hamptons on the Hudson in South Saugerties
Pool

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (14)
"We had an absolutely wonderful stay at this Vrbo! From the moment we arrived, everything was spotless, beautifully decorated, and thoughtfully equipped with everything we needed. The hosts went above and beyond to ensure a comfortable and seamless experience, providing clear instructions and even thoughtful touches that made us feel right at home.The location was perfect—close enough to attractions and restaurants but still peaceful and private. The beds were incredibly comfortable, the kitchen...
Hamptons on the Hudson in South Saugerties
Streamside Cottage Half Mile to Town of Woodstock
Front Entrance to Cottage

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (228)
"We totally enjoyed our stay at the cottage! Exactly as advertised, except the views of the river from the home are are even better than pictured. We would definitely recommend!"
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.