Annandale-on-Hudson Vacation Rentals

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Browse Select Annandale-on-Hudson Vacation Homes

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (46)
"4 of us stayed for a fishing trip and had a blast. Nice place at a reasonable price. Would stay again. "
The price is CA $206
CA $335 total
includes taxes & fees
Aug 24 - Aug 25
Esopus Creek modern Tiny house Retreat!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

Secluded family retreat within minutes of Woodstock village

10.0 out of 10, Exceptional, (42)
"My wife and I came for just the weekend and enjoyed the house as always! Comfortable, clean, spacious, and convenient to everything yet quiet as can be. "
Secluded family retreat within minutes of Woodstock village

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

Quaint Cottage w/ Peloton & Sauna near Hiking

9.4 out of 10, Exceptional, (22)
"Nice area, cute cottage."
Quaint Cottage w/ Peloton & Sauna near Hiking

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (5)
"We had a 2 night stay while in Catskill for a wedding. My hubby, 8 year old and 2 dogs in tow. House was just right for us. My son loved the board games available and the foosball table. House is uncluttered and very clean. Surrounding are is historic with a short walk to downtown shops. I would definitely rent here again. "
Charming Catskill getaway walking distance to Main St. Pet-friendly!

2025 Sheep & Wool Weekend Now Available !!

10.0 out of 10, Exceptional, (45)
"We loved the area lots to do great restaurants"
2025 Sheep & Wool Weekend Now Available !!

Cozy year round retreat! Close to skiing, hiking and swimming.

10.0 out of 10, Exceptional, (49)
"Summer in the Catskills is a treat and these are the accommodations to enjoy it to its fullest. Can’t wait to stay again!"
Cozy year round retreat! Close to skiing, hiking and swimming.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park

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

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (131)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain

9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres

9.8 out of 10, Exceptional, (7)
"Amazing home, fantastic host. Beautiful decor, comfortable beds and great amenities. Host was very friendly and responsive. Couldn't have asked for a better vacation. "
9BR/5BR/Hottub/2 Saunas 6 min to Hunter on 30 private acres

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (139)
"If you’re looking for a quiet, hidden retreat with endless things to do, this is your spot! Such a gem tucked away into the woods. "
<br>Escape to our incredibly private home on 30 acres!

Peaceful Cabin w/ Fire Pit & Creek Access

10.0 out of 10, Exceptional, (7)
"Great little space , clean, comfortable and equipped with everything I needed for a nice weekend! Would stay again if ever I return to the area ."
The price is CA $115
CA $321 total
includes taxes & fees
Sep 9 - Sep 10
Peaceful Cabin w/ Fire Pit & Creek Access

Bohemian style open LOFT

9.2 out of 10, Wonderful, (14)
"We had a wonderful stay at Stojan’s property! Great spot for a weekend getaway and Stojan was very helpful and responsive if/when needed. Highly recommend! "
Bohemian style open LOFT

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

10.0 out of 10, Exceptional, (64)
"This was an excellent place to stay in such a beautiful area."
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (28)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

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

9.6 out of 10, Exceptional, (30)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

10.0 out of 10, Exceptional, (183)
"The property was perfect! Beautiful, secluded & very welcoming "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter

10.0 out of 10, Exceptional, (48)
"We loved our time out here and hope to be back soon!"
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
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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Top Annandale-on-Hudson Hotel Reviews