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Annandale-on-Hudson Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Annandale-on-Hudson vacation rentals

A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

1. 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.
$216 nightly
The price is $244
Oct 31 - Nov 1
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A wall-mounted air conditioning unit with a digital display.

2. 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.
$251 nightly
The price is $284
Nov 3 - Nov 4
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

3. 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.
$226 nightly
The price is $253
Nov 3 - Nov 4
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

4. 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, (7 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.
$221 nightly
The price is $248
Oct 28 - Oct 29
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

5. 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, (327 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
$192 nightly
The price is $207
Nov 24 - Nov 25
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

6. 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
$263 nightly
The price is $295
Nov 17 - Nov 18
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
A living room with a white armchair, a grey sofa, a large green plant, and a wooden coffee table. A staircase with white railings leads to an upper floor.

7. Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Saugerties
10.0 out of 10, Exceptional, (5 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
$466 nightly
The price is $522
Oct 28 - Oct 29
Total with taxes and fees
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
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.

8. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
$237 nightly
The price is $265
Nov 2 - Nov 3
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
A kitchen with a white stove, a coffee maker, and a microwave on the counter.

9. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Both the house and host were great. The house was in great shape, clean, comfy and with anything we might needed. 100% recommend!!"
United States
Matias
$207 nightly
The price is $232
Nov 3 - Nov 4
Total with taxes and fees
Butterfly Bungalow Studio · Saugerties/Woodstock
A living room with a stone fireplace, a ceiling fan, a leather armchair, a bookshelf, and a rug.

10. Hudson Landing - Fireplace & Catskills Retreat

Hudson Landing - Fireplace & Catskills Retreat
Saugerties
$608 nightly
The price is $681
Oct 28 - Oct 29
Total with taxes and fees
Hudson Landing - Fireplace & Catskills Retreat
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

11. 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.
$589 nightly
The price is $665
Nov 9 - Nov 10
Total with taxes and fees
Creek Views * Chef’s Kitchen * Walk To Lighthouse
Private kitchen

12. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (15 reviews)
"Thank you. What an experience!"
United States
Burc
$180 nightly
The price is $202
Nov 10 - Nov 11
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
A kitchen with white cabinetry, granite countertops, and a window with blinds.

13. 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, (16 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$227 nightly
The price is $254
Nov 16 - Nov 17
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
A hot tub in a natural setting with a tree and a body of water.

14. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (17 reviews)
"A nice relaxing spot."
United States
Darren F.
$361 nightly
The price is $404
Oct 26 - Oct 27
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
A staircase with a metal handrail and a bench with a striped cushion.

15. 3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!

3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
Saugerties
10.0 out of 10, Exceptional, (3 reviews)
"Great location, very well-stocked. Would absolutely stay here again."
United States
Kristen R.
$451 nightly
The price is $506
Nov 2 - Nov 3
Total with taxes and fees
3BR Farmhouse in the Village of Saugerties - Hike Upstate - Walk to it all!
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.

16. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$230 nightly
The price is $258
Nov 1 - Nov 2
Total with taxes and fees
Gatherwild Ranch
A modern living room with a sofa, a coffee table, and a dining table. There are two doors, one black and one white, and a window with blinds.

17. Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 reviews)
"The rental was very clean & Beds were very comfortable. "
United States
R.A.G. Time A.
$257 nightly
The price is $288
Nov 3 - Nov 4
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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.

18. 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, (3 reviews)
"Lovely, clean, quiet house. Exactly what we needed for a place to stay while we were showing at HITS. Would definitely stay here again!"
United States
Charlotte J.
$529 nightly
The price is $592
Oct 27 - Oct 28
Total with taxes and fees
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
An outdoor patio with a striped rug, seating, a fire pit, and string lights.

19. 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, (38 reviews)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$237 nightly
The price is $265
Nov 2 - Nov 3
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
A view from a room with a sliding glass door leading to an outdoor deck with a wooden fence, a chair, and a bench.

20. 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, (108 reviews)
"Wonderful stay. Lovely tiny house in a beautiful wooded setting. Woke to the sounds of birds singing. Would stay again"
United States
Nan
$223 nightly
The price is $249
Nov 9 - Nov 10
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Soooo good! Lovely, unique, peaceful. Walking distance to all the shops! 10/10!"
Liza 3-night trip
Posted 10 hours ago
Pocketbook Hotel and Bath

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 $201 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?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Annandale-on-Hudson is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.