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Annandale-on-Hudson Vacation Rentals

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Annandale-on-Hudson vacation rentals

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

1. 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, (309 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Oct 26 - Oct 27
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A hot tub in a natural setting with a tree and a body of water in the background.

2. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"A nice relaxing spot."
United States
Darren F.
$373 nightly
The price is $418
Sep 27 - Sep 28
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

3. THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Red Hook
9.2 out of 10, Wonderful, (15 reviews)
"Very sweet little spot that took care of all our needs. Very grateful to have found it and enjoyed our stay."
United States
Jason D.
$210 nightly
The price is $238
Oct 7 - Oct 8
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A kitchen with white cabinetry, granite countertops, and a window with blinds.

4. 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, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$219 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

5. 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, (103 reviews)
"Wonderful stay. "
United States
Chris L.
$231 nightly
The price is $259
Sep 27 - Sep 28
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

6. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$228 nightly
The price is $255
Oct 26 - Oct 27
Total with taxes and fees
Gatherwild Ranch
A modern house with a hot tub, a deck, and a view of a lake.

7. Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!

Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!
Saugerties
10.0 out of 10, Exceptional, (18 reviews)
"Great stay! Would definitely go back!"
United States
Alexis
$777 nightly
The price is $877
Sep 28 - Sep 29
Total with taxes and fees
Chic Waterfront w/ Hot Tub, Sauna and Sky Deck!
A living room with a grey sofa, patterned cushions, a side table with a lamp, and large windows offering a view of a snowy landscape.

8. Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Saugerties
10.0 out of 10, Exceptional, (2 reviews)
"Perfect for our group of 6"
United States
Patricia S.
$506 nightly
The price is $567
Sep 27 - Sep 28
Total with taxes and fees
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

9. Creek Views * Chef’s Kitchen * Walk To Lighthouse

Creek Views * Chef’s Kitchen * Walk To Lighthouse
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"this house was very comfortable and convenient to Saugerties"
United States
molly f.
$540 nightly
The price is $610
Sep 29 - Sep 30
Total with taxes and fees
Creek Views * Chef’s Kitchen * Walk To Lighthouse
An outdoor deck with a wooden deck, a grill, wicker chairs, and a red umbrella.

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

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$425 nightly
The price is $476
Sep 27 - Sep 28
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

11. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
$230 nightly
The price is $260
Sep 29 - Sep 30
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

12. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
$230 nightly
The price is $258
Oct 6 - Oct 7
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
A natural setting with a stream, red chairs, and a forested area.

13. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (299 reviews)
"It was the perfect place for a weekend away from home! The location was only a few minutes from town and was the perfect size for a couple. Would definitely reccomend!"
United States
Kristen S.
$268 nightly
The price is $300
Sep 27 - Sep 28
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
A hot tub with a view of a lake and a dock.

14. Hot tub on water, 5min HITS, 20mi to Hunter skiing

Hot tub on water, 5min HITS, 20mi to Hunter skiing
Malden
10.0 out of 10, Exceptional, (7 reviews)
"The house was very comfortable and clean. Kitchen was well appointed. Drawers and cabinets are well stocked w general utensils."
United States
Penny R.
$828 nightly
The price is $896
Sep 27 - Sep 28
Total with taxes and fees
Hot tub on water, 5min HITS, 20mi to Hunter skiing
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

15. 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, (37 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$230 nightly
The price is $257
Oct 7 - Oct 8
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A spacious living area with a dining table, sofa, and large windows offering a view of the outdoors.

16. 3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly

3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly
Kingston
10.0 out of 10, Exceptional, (3 reviews)
"great host and property! recommended and would go back."
United States
Themis H.
$478 nightly
The price is $535
Sep 28 - Sep 29
Total with taxes and fees
3BR Modern Home in Kingston - Sleeps 6 -Fire Pit -Game Room -Pet Friendly
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

17. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$231 nightly
The price is $259
Sep 28 - Sep 29
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A balcony with wicker furniture, a view of a lake, and a grassy area with outdoor seating.

18. Creekside Escape- Kayaks, Paddleboards, Hot Tub, Sauna & Fire Pit

Creekside Escape- Kayaks, Paddleboards, Hot Tub, Sauna & Fire Pit
Saugerties
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful property with great amenities! Wphld definitely stay there again!"
United States
Andrew L.
$902 nightly
The price is $1,010
Sep 28 - Sep 29
Total with taxes and fees
Creekside Escape- Kayaks, Paddleboards, Hot Tub, Sauna & Fire Pit

19. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (12 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.
$179 nightly
The price is $200
Sep 29 - Sep 30
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"The room was spacious and clean, with a refrigerator, a coffee Maher and a microwave. The breakfast was nice, and the bar at the hotel was pleasant during the cocktail hour."
Elena 1-night trip
Posted 5 hours ago
Beekman Arms and Delamater Inn

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 $167 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?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental outside of Annandale-on-Hudson offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.