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Annandale-on-Hudson Holiday Rentals

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Our top choices for Annandale-on-Hudson holiday rentals

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 NZ$443
includes taxes & fees
9 Sept - 10 Sept
Stunning and Cozy loft apartment in kingston .

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)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is NZ$386
includes taxes & fees
11 Sept - 12 Sept
Charming loft cottage in tranquil Germantown with WiFi, AC

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 NZ$755
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

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 NZ$478
includes taxes & fees
9 Sept - 10 Sept
Campfire Cottage: Fireplace, fire pit & no chores!

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 NZ$514
includes taxes & fees
1 Sept - 2 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

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)
The price is NZ$681
includes taxes & fees
12 Aug - 13 Aug
Peaceful Riverfront Cottage with Private Hot tub

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 NZ$340
includes taxes & fees
17 Aug - 18 Aug
Woods Cabin-Kingston/Woodstock, NY.

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, (95 reviews)
"Wonderful stay. "
United States
Chris L.
The price is NZ$445
includes taxes & fees
8 Sept - 9 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

9. '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, (48 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 NZ$252
includes taxes & fees
12 Aug - 13 Aug
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

10. 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, (269 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is NZ$368
includes taxes & fees
9 Sept - 10 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

11. 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 NZ$407
includes taxes & fees
9 Sept - 10 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

12. 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 NZ$476
includes taxes & fees
13 Aug - 14 Aug
Hot Tub - Fire Pit - BBQ - Hammock - Colonial

13. 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 NZ$986
includes taxes & fees
20 Aug - 21 Aug
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties

14. 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 NZ$1,166
includes taxes & fees
8 Sept - 9 Sept
Super Comfortable Water-view Home in Saugerties

15. 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.
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties

16. 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 NZ$611
includes taxes & fees
8 Sept - 9 Sept
Retro Retreat: renovated 2BR, desk, no chore list!

17. 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, (34 reviews)
"The beds were especially comfortable! "
United States
josh p.
The price is NZ$516
includes taxes & fees
19 Aug - 20 Aug
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

18. 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 NZ$855
includes taxes & fees
12 Aug - 13 Aug
Umana's Cabin, cozy, comfy, 5+ acres of land

19. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (293 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 NZ$572
includes taxes & fees
8 Sept - 9 Sept
Streamside Cottage Half Mile to Town of Woodstock

20. 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 NZ$442
includes taxes & fees
12 Aug - 13 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.
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Top Annandale-on-Hudson Hotel Reviews

Find out more about Annandale-on-Hudson

Everything you need to know about Annandale-on-Hudson holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annandale-on-Hudson holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annandale-on-Hudson holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annandale-on-Hudson holiday rentals we have selected for you start as low as NZ$252 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 holiday 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 holiday.

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 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 Falling Waters Preserve. 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.