Annandale-on-Hudson Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Annandale-on-Hudson Vacation Homes

The Farm at Hyde Park
Set amidst lush greenery and mature trees, this charming building features a steeply pitched roof and a brick facade.

The Farm at Hyde Park

9.8 out of 10, Exceptional, (75)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Cozy year round retreat! Close to skiing, hiking and swimming.
Relax on the covered deck with Adirondack chairs, a table, and a grill for outdoor cooking.

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

10.0 out of 10, Exceptional, (48)
"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.
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Enjoy a peaceful forest view from the large window, featuring a comfortable bed below.

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (176)
"Loved our stay and the house. Everything was wonderful. I will say it was a little farther than 'a walk into town' and we did Uber everywhere. Everything at the house was great - nice relaxing spot!!"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Esopus Creek modern Tiny house Retreat!
Enjoy a romantic dinner for two on this deck with a beautiful floral arrangement and a bottle of wine.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (45)
"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 $204
CA $332 total
includes taxes & fees
Aug 17 - Aug 18
Esopus Creek modern Tiny house Retreat!
Charming cottage with lake access, wood burning fire place, and WiFi
Relax in this inviting living room with a sofa, dresser, and small table.

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

2.0 star property
9.0 out of 10, Wonderful, (7)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Relax in a spacious bedroom with a large bed, bedside table, and lamp, offering a view of the balcony and adjacent room.

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
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Enjoy cooking in this well-lit kitchen with a central island and modern appliances.

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

10.0 out of 10, Exceptional, (3)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Enjoy cooking in this well-lit kitchen with a central island and stainless steel appliances.

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
Secluded family retreat within minutes of Woodstock village
Relax on the deck with a sofa, armchairs, and ottomans, taking in the view of the wooded area.

Secluded family retreat within minutes of Woodstock village

10.0 out of 10, Exceptional, (41)
"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
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Relax by the serene pool surrounded by lush greenery and trees.

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

10.0 out of 10, Exceptional, (63)
"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!
Stylish Cozy Home with Gorgeous Views!
Enjoy cooking in this well-equipped kitchen with a central island and modern appliances.

Stylish Cozy Home with Gorgeous Views!

10.0 out of 10, Exceptional, (25)
"Second time staying here; check in and out is super easy. Place is beautiful and comfortable. Perfect place to relax."
Stylish Cozy Home with Gorgeous Views!
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
Relax in a serene outdoor setting surrounded by a mature tree and beautifully manicured lawn.

Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay

9.6 out of 10, Exceptional, (76)
"House was very clean. Property managers were very responsive to check in and check out time and anything we needed during our stay. Very close to the mountain and beautiful location. Would highly recommend."
Heart of Hunter Village; across MT!FaLL Special3rd nt half OFF!”wknd stay
Super Comfortable Water-view Home in Saugerties
Relax in a spacious living area with a pool table, dining space, and cozy seating area.

Super Comfortable Water-view Home in Saugerties

9.6 out of 10, Exceptional, (4)
"A very clean, spacious, and friendly environment with all the amenities you need. "
The price is CA $349
CA $999 total
includes taxes & fees
Sep 10 - Sep 11
Super Comfortable Water-view Home in Saugerties
Beautiful new house 3/4 mile from Hunter Mountain
Cozy cabin with a central entrance and windows on either side, set amidst a serene winter landscape.

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (130)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
Stylish Pine Plains Home Near Parks & Hiking!
Enjoy cooking in this fully equipped kitchen with a range, oven, microwave, and sink.

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (15)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!
Hamptons on the Hudson in South Saugerties
Relax in a cozy outdoor space with a fireplace, wicker furniture, and a scenic view.

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (24)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Experience a cozy retreat with a neatly made bed, wooden dresser, and dining area.

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

10.0 out of 10, Exceptional, (89)
"Our first experience staying at a yurt. It was cozy and comfortable with everything you might need. The property was beautiful as well."
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Enjoy cooking in this well-equipped kitchen with a dining area nearby.

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Traditional home with a central entrance, flanked by windows, surrounded by a well-maintained lawn and a large tree.

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

10.0 out of 10, Exceptional, (112)
"Amazing Woodstock location!"
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Catskill Country House w/ Hot Tub Near Hiking
Enjoy meals in this serene conservatory with a round dining table and garden views.

Catskill Country House w/ Hot Tub Near Hiking

9.6 out of 10, Exceptional, (13)
"Another great stay"
Catskill Country House w/ Hot Tub Near Hiking
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

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

10/10 Excellent
"Very clean. Great staff. Always willing to help I’d stay there again. "
Steve 6-night trip
Posted 2 days ago
Holiday Inn Express & Suites Kingston-Ulster by IHG