Default HTG hotel image

Annandale-on-Hudson Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Annandale-on-Hudson holiday rentals

Interior

1. 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 HK$1,177
HK$2,109 total
includes taxes & fees
19 Aug - 20 Aug
Stunning and Cozy loft apartment in kingston .
Interior

2. 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, (12 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is HK$1,083
HK$1,960 total
includes taxes & fees
9 Sept - 10 Sept
Charming loft cottage in tranquil Germantown with WiFi, AC
Living area

3. Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook
10.0 out of 10, Exceptional, (26 reviews)
"It was pet friendly, even for a dog, was comfortable for the entire family and is a great location with easy access to surrounding villages."
United States
Susan T.
The price is HK$1,942
HK$3,529 total
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Interior

4. 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.
The price is HK$753
HK$2,197 total
includes taxes & fees
13 Sept - 14 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
1 bedroom, desk, free WiFi, bed sheets

5. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (31 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$1,024
HK$2,339 total
includes taxes & fees
19 Aug - 20 Aug
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Outdoor spa tub

6. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"We loved our stay here. It was a beautiful location and central to the places we wanted to visit. It looked brand new and it was very clean. It was quiet and peaceful. The hosts even had little snacks for us which was a nice touch."
United States
Laura M.
The price is HK$1,875
HK$3,506 total
includes taxes & fees
17 Aug - 18 Aug
Peaceful Riverfront Cottage with Private Hot tub
Private kitchen

7. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (7 reviews)
"The cabin is awesome. Surrounded by forrest you feel like youre the only person in the world. What's even cooler is its off grid but you dont miss a thing. Lights. Music. Bathroom. There were even a couple board games. Outside fire ready to go. Exactly what I was looking for."
United States
Carrie
The price is HK$895
HK$1,591 total
includes taxes & fees
18 Aug - 19 Aug
Woods Cabin-Kingston/Woodstock, NY.
Interior

8. 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, (97 reviews)
"Wonderful stay. "
United States
Chris L.
The price is HK$1,342
HK$2,118 total
includes taxes & fees
30 Aug - 31 Aug
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Exterior

9. 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, (273 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is HK$1,263
HK$1,703 total
includes taxes & fees
13 Sept - 14 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, fridge, microwave, oven

10. 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 HK$573
HK$1,942 total
includes taxes & fees
13 Sept - 14 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Smart TV

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

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (29 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 HK$981
HK$2,180 total
includes taxes & fees
10 Sept - 11 Sept
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Smart TV, fireplace

12. 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, (1 review)
"Perfect for our group of 6"
United States
Patricia S.
The price is HK$2,158
HK$4,737 total
includes taxes & fees
20 Aug - 21 Aug
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Dining

13. Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"Very comfortable home, everything that’s needed is there "
United States
gianni g.
The price is HK$1,718
HK$5,464 total
includes taxes & fees
14 Sept - 15 Sept
Super Comfortable Water-view Home in Saugerties
Living area

14. 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 HK$2,288
HK$5,577 total
includes taxes & fees
30 Aug - 31 Aug
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
2 bedrooms, desk, free WiFi, bed sheets

15. 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 HK$1,028
HK$2,777 total
includes taxes & fees
13 Sept - 14 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
Terrace/patio

16. 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, (35 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is HK$989
HK$2,259 total
includes taxes & fees
19 Aug - 20 Aug
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Outdoor dining

17. 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
The price is HK$2,112
HK$3,982 total
includes taxes & fees
16 Aug - 17 Aug
Umana's Cabin, cozy, comfy, 5+ acres of land
Property grounds

18. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (294 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveller
The price is HK$1,123
HK$2,497 total
includes taxes & fees
7 Sept - 8 Sept
Streamside Cottage Half Mile to Town of Woodstock
Dining

19. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (16 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
The price is HK$1,024
HK$2,070 total
includes taxes & fees
16 Aug - 17 Aug
Charming Yacht on Catskill Creek
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annandale-on-Hudson Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"Charming, and Historic!!"
Raymond 2-night trip
Posted 5 hours ago
Beekman Arms and Delamater Inn

Find out more about Annandale-on-Hudson

Search for holiday rentals in Annandale-on-Hudson on Expedia! You can easily find your home rentals, villas, holiday apartments in Annandale-on-Hudson using one of the methods below:

  • View our selection of featured holiday rentals in Annandale-on-Hudson
  • Use the map to find apartments and other holiday homes in the Annandale-on-Hudson neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Annandale-on-Hudson while they last

Look no further and take a look at our great range of rental properties in Annandale-on-Hudson!

Frequently asked questions

Are there holiday rentals in Annandale-on-Hudson?

Yes, there are holiday rentals close to the most popular sights in Annandale-on-Hudson, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Annandale-on-Hudson has to offer?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This holiday home rental outside of Annandale-on-Hudson is located on a river, and has a fireplace, a patio and a BBQ 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 that 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 Poet's Walk Park. In the wider area, you’ll find Bard College and Hessel Museum of Art.

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

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annandale-on-Hudson. Holiday rentals feature extras such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family gatherings.