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Annandale-on-Hudson Vacation Rentals

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Our top choices for Annandale-on-Hudson vacation rentals

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (253 reviews)
"Really great location and near great area."
United States
Sherwin
The price is CA $254
CA $336 total
includes taxes & fees
Aug 3 - Aug 4
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

'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.
The price is CA $177
CA $230 total
includes taxes & fees
Jul 12 - Jul 13
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
10.0 out of 10, Exceptional, (3 reviews)
"Oh, I gave this property excellent scores for all the questions but I am reminded now by the suggestions for what to write about about the fact that it listed an Ocean view, which is obviously a mistake. It’s nowhere near the ocean. There’s no ocean view. It is in the woods it’s secluded.I actually took a very little walk in the middle of the night in the dark using my cell phone flashlight and got kind of lost for a while, but managed to find my way back. That was quite an interesting...
United States
Michael H.
The price is CA $162
CA $245 total
includes taxes & fees
Jul 6 - Jul 7
Woods Cabin-Kingston/Woodstock, NY.

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet
Stone Ridge
8.6 out of 10, Excellent, (17 reviews)
"Cozy, clean, and extremely accommodating. Everything was planned out well and the sauna was lovely in such cold weather! Would highly recommend for anyone considering travel to this beautiful region of New York!"
United States
Avi
The price is CA $81
CA $191 total
includes taxes & fees
Jul 7 - Jul 8
Hudson Valley Apartment in a Historic Farmhouse w/ Sauna Near Stone Ridge Hamlet

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.
The price is CA $211
CA $404 total
includes taxes & fees
Jul 5 - Jul 6
Private Yacht on Catskill Creek

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (28 reviews)
"Wonderful apartment with everything our family of five needed. We enjoyed the hot tub on two snowy evenings. Thank you for a great stay!"
United States
Clara L.
The price is CA $147
CA $360 total
includes taxes & fees
Jul 7 - Jul 8
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Jessie's Harvest House

Jessie's Harvest House
Tannersville
10.0 out of 10, Exceptional, (2 reviews)
"cute little spot! very nice place to stay"
United States
David R.
The price is CA $224
CA $358 total
includes taxes & fees
Jul 7 - Jul 8
Jessie's Harvest House

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (32 reviews)
"Lovely place almost magical ....the perfect get away . . So well kept."
United States
Nivia
The price is CA $287
CA $529 total
includes taxes & fees
Jul 6 - Jul 7
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (88 reviews)
"Perfect for us passing through"
United States
Chris S.
The price is CA $235
CA $374 total
includes taxes & fees
Jul 8 - Jul 9
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Kingston
9.2 out of 10, Wonderful, (32 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is CA $179
CA $407 total
includes taxes & fees
Jul 5 - Jul 6
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

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.
The price is CA $255
CA $508 total
includes taxes & fees
Jul 6 - Jul 7
Charming Cottage in the Heart of Catskill & Pet Friendly

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.
The price is CA $129
CA $393 total
includes taxes & fees
Jul 16 - Jul 17
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is CA $227
CA $491 total
includes taxes & fees
Jul 8 - Jul 9
Modern Luxurious Cabin, Catskills - The Tiny Nook

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (11 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is CA $204
CA $370 total
includes taxes & fees
Jul 29 - Jul 30
Charming loft cottage in tranquil Germantown with WiFi, AC

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, (17 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is CA $228
CA $501 total
includes taxes & fees
Jul 23 - Jul 24
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi
Woodstock
10.0 out of 10, Exceptional, (13 reviews)
"In the heart of woodstock, walking distance to any of the shops and restaurants, even grocery stores!! For the low price, it was a great place to stay, great quiet area and felt so safe!"
United States
Eden C.
The price is CA $152
CA $409 total
includes taxes & fees
Jul 7 - Jul 8
Colorful Modern Hideaway In Downtown Woodstock - AC & WiFi

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, (40 reviews)
"We Absolutely loved our weekend stay here! Beautiful property and just as described!!! Will definitely be back!!!"
United States
Jessica R.
The price is CA $320
CA $627 total
includes taxes & fees
Jul 30 - Jul 31
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

West Wing - a unique private space w/patio

West Wing - a unique private space w/patio
Shokan
9.8 out of 10, Exceptional, (26 reviews)
"I enjoyed my stay at this lovely, clean, cozy home."
United States
Taela
The price is CA $179
CA $282 total
includes taxes & fees
Jul 15 - Jul 16
West Wing - a unique private space w/patio

Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
The price is CA $133
CA $246 total
includes taxes & fees
Jul 9 - Jul 10
Jessie's Harvest House Suite

Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is CA $244
CA $320 total
includes taxes & fees
Jul 6 - Jul 7
Hudson Valley Farm Getaway- West/Llama Lover Lane
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

Find out more about Annandale-on-Hudson

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Annandale-on-Hudson. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This vacation home rental outside of Annandale-on-Hudson is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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

While exploring the area, visit family-friendly sights like Hudson River Maritime Museum, 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.