Annandale-on-Hudson Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Annandale-on-Hudson vacation rentals

Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (230 reviews)
"Really great location and near great area."
United States
Sherwin
$192 nightly
The price is $207
Jun 22 - Jun 23
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.0 out of 10, Very Good, (47 reviews)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
May 27 - May 28
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.6 out of 10, Exceptional, (39 reviews)
"The house was beautiful, clean, and filled with helpful amenities! "
United States
John C.
$321 nightly
The price is $360
May 25 - May 26
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Fridge, oven, stovetop, coffee/tea maker

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (4 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
$174 nightly
The price is $197
Jun 4 - Jun 5
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Terrace/patio

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.4 out of 10, Exceptional, (28 reviews)
"The beds were especially comfortable! "
United States
josh p.
$231 nightly
The price is $258
May 26 - May 27
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Outdoor dining

Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (24 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
$315 nightly
The price is $353
May 25 - May 26
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Interior

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (15 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
$279 nightly
The price is $301
May 26 - May 27
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Smart TV, fireplace

Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
$180 nightly
The price is $204
May 27 - May 28
Total with taxes and fees
Private, Cozy, Clean apartment in lovely Hyde Park
Fridge, microwave, oven, stovetop

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
$226 nightly
The price is $253
May 27 - May 28
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (31 reviews)
"Lovely place almost magical ....the perfect get away . . So well kept."
United States
Nivia
$346 nightly
The price is $373
May 25 - May 26
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Outdoor dining

Private Yacht on Catskill Creek

Private Yacht on Catskill Creek
Catskill
9.8 out of 10, Exceptional, (28 reviews)
"Host was very responsive and ensured a fun stay for us."
United States
Yannie C.
$255 nightly
The price is $285
May 25 - May 26
Total with taxes and fees
Private Yacht on Catskill Creek
Interior

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
$250 nightly
The price is $280
May 27 - May 28
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
Bar (on property)

Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (1 review)
"cute little spot! very nice place to stay"
United States
David R.
$189 nightly
The price is $200
Jun 2 - Jun 3
Total with taxes and fees
Jessie's Harvest House
Smart TV, books

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
Woodstock
10.0 out of 10, Exceptional, (11 reviews)
"We loved the location right in town , excellent! Great shops, bars and restaurants within a short walking distance. We loved the room too. About the only improvement I can think of is if you upgraded the couch to a full size one. We will book again the next time we go to Woodstock. "
United States
Scott M.
$257 nightly
The price is $287
May 27 - May 28
Total with taxes and fees
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
2 bedrooms, desk, free WiFi, bed sheets

Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
$307 nightly
The price is $344
May 27 - May 28
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
Desk, WiFi

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
$482 nightly
The price is $540
May 26 - May 27
Total with taxes and fees
Charles Cottage Near Warren St New Renovation
TV, fireplace, books

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!
Lanesville
10.0 out of 10, Exceptional, (3 reviews)
"Had a wonderful weekend getaway here. The property is just as described, awesome communication and recs, and VERY convenient to the mountain. Would highly recommend if you are looking to relax and unwind away from the crowds that the nearby hotels have. Very conveniently located to some great restaurants and cafes. Thoroughly enjoyed ourselves! "
United States
Krista F.
$213 nightly
The price is $231
May 27 - May 28
Total with taxes and fees
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Unwind!
Property grounds

Cozy Downtown Hunter Mountain Getaway

Cozy Downtown Hunter Mountain Getaway
Lanesville
$174 nightly
The price is $188
May 27 - May 28
Total with taxes and fees
Cozy Downtown Hunter Mountain Getaway
TV, fireplace, video games, stereo

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!

Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
Hunter Highlands
10.0 out of 10, Exceptional, (22 reviews)
"You will definitely return this place is cozy, clean and convenient! "
United States
Elizabeth C.
$213 nightly
The price is $231
May 27 - May 28
Total with taxes and fees
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$456 nightly
The price is $511
May 25 - May 26
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
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

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

10/10 Excellent
"It was great will definitely be back!!"
Latisha 1-night trip
Posted 2 hours ago
Courtyard by Marriott Kingston

Find out more about Annandale-on-Hudson

Everything you need to know about Annandale-on-Hudson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annandale-on-Hudson vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annandale-on-Hudson vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annandale-on-Hudson vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annandale-on-Hudson. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Annandale-on-Hudson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $162 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annandale-on-Hudson rentals

At Expedia, we put the best Annandale-on-Hudson vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annandale-on-Hudson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annandale-on-Hudson vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annandale-on-Hudson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Annandale-on-Hudson?

Yes, you can find vacation rentals near well known local attractions in Annandale-on-Hudson, or you can select a more remote option if you're looking for relaxation. Annandale-on-Hudson is known for its university setting and art. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation rentals that Annandale-on-Hudson has to offer?

The Farm at Hyde Park: This vacation home rental outside of Annandale-on-Hudson is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Annandale-on-Hudson?

While exploring the area, visit family-friendly sights like Kiwanis Ice Arena, or get outside and enjoy nature at Falling Waters Preserve. In the larger area, you’ll find Bard College and Hessel Museum of Art.

What are vacation rentals like in Annandale-on-Hudson?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Annandale-on-Hudson. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.