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Annandale-on-Hudson Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
The price is CA $185
CA $319 total
includes taxes & fees
Oct 8 - Oct 9
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

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.
The price is CA $176
CA $410 total
includes taxes & fees
Nov 3 - Nov 4
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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.

3. 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, (3 reviews)
"Very comfortable accommodation, beds and pillows are wonderful!"
United States
Danita K.
The price is CA $208
CA $749 total
includes taxes & fees
Oct 28 - Oct 29
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

4. 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.
The price is CA $199
CA $871 total
includes taxes & fees
Nov 3 - Nov 4
Creek Views * Chef’s Kitchen * Walk To Lighthouse
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, (319 reviews)
"Excellent place"
United States
Yeudin
The price is CA $230
CA $310 total
includes taxes & fees
Nov 5 - Nov 6
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

6. 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.
The price is CA $124
CA $379 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

7. 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 $98
CA $342 total
includes taxes & fees
Nov 3 - Nov 4
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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, (17 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is CA $213
CA $379 total
includes taxes & fees
Oct 12 - Oct 13
Stunning and Cozy loft apartment in kingston .
A kitchen with white cabinetry, granite countertops, and a window with blinds.

9. 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.
The price is CA $182
CA $377 total
includes taxes & fees
Oct 8 - Oct 9
Charming loft cottage in tranquil Germantown with WiFi, AC
A kitchen with a stove, cabinets, and a microwave.

10. 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
The price is CA $69
CA $312 total
includes taxes & fees
Oct 13 - Oct 14
Butterfly Bungalow Studio · Saugerties/Woodstock
A staircase with a metal handrail and a bench with a striped cushion.

11. 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.
The price is CA $295
CA $700 total
includes taxes & fees
Nov 3 - Nov 4
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.

12. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is CA $317
CA $386 total
includes taxes & fees
Oct 20 - Oct 21
Gatherwild Ranch
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

13. 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
The price is CA $135
CA $439 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: renovated 2BR, desk, no chore list!
Private kitchen

14. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (13 reviews)
"The Woods Cabin was exactly what it said it was; a teeny tiny, relatively new cabin pretty deep in the scrubby woods of rural NY. It was clean and fully functional, but it was very basic—it was much more than a tent, but the experience was not at all “glamping.” The owner was exceptionally responsive and helpful…no complaints there, or anywhere! As I said, the Woods Cabin is/was exactly what it said it was. Nothing more; nothing less."
United States
Nora Tracy
The price is CA $162
CA $290 total
includes taxes & fees
Oct 20 - Oct 21
Woods Cabin-Kingston/Woodstock, NY.
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.

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

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (33 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 $173
CA $392 total
includes taxes & fees
Oct 28 - Oct 29
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.

16. 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.
The price is CA $391
CA $856 total
includes taxes & fees
Oct 12 - Oct 13
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
A hot tub in a natural setting with a tree and a body of water.

17. 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.
The price is CA $340
CA $630 total
includes taxes & fees
Oct 20 - Oct 21
Peaceful Riverfront Cottage with Private Hot tub
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is CA $160
CA $298 total
includes taxes & fees
Oct 19 - Oct 20
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A sectional sofa with matching ottomans, a small table with a lamp, and a patterned rug on a wooden floor.

19. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
The price is CA $192
CA $495 total
includes taxes & fees
Oct 27 - Oct 28
Country House offers 2 bedrooms and a den, lots of parking.
A hot tub with a view of a lake and a dock.

20. 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.
The price is CA $461
CA $1,274 total
includes taxes & fees
Oct 13 - Oct 14
Hot tub on water, 5min HITS, 20mi to Hunter skiing
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

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

8/10 Good
"Our tv was not working ac and heating was weird unit was seating on the floor and vent on the ceiling was out of control and front desk was unable to do anything."
Shri G 1-night trip
Posted less than an hour ago
Residence Inn 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annandale-on-Hudson vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annandale-on-Hudson vacation rentals we have selected for you start as low as CA $284 per night. Entering your travel dates in the search wizard 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. 

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.