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Annandale-on-Hudson Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Annandale-on-Hudson holiday rentals

Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (32 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$682
HK$2,134 total
includes taxes & fees
23 Sept - 24 Sept
Campfire Cottage: Fireplace, fire pit & no chores!
Private kitchen

2. 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$541
HK$1,941 total
includes taxes & fees
22 Sept - 23 Sept
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Exterior

3. '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
8.2 out of 10, Very good, (49 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 HK$882
HK$1,163 total
includes taxes & fees
26 Aug - 27 Aug
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Room

4. 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$1,082
HK$2,412 total
includes taxes & fees
1 Sept - 2 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Interior

5. 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, (13 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
The price is HK$1,011
HK$1,888 total
includes taxes & fees
22 Sept - 23 Sept
Charming loft cottage in tranquil Germantown with WiFi, AC
Private kitchen

6. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.4 out of 10, Exceptional, (9 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$894
HK$1,589 total
includes taxes & fees
26 Aug - 27 Aug
Woods Cabin-Kingston/Woodstock, NY.
Interior

7. 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$1,176
HK$2,107 total
includes taxes & fees
30 Aug - 31 Aug
Stunning and Cozy loft apartment in kingston .
Room

8. 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$925
HK$2,696 total
includes taxes & fees
23 Sept - 24 Sept
Retro Retreat: renovated 2BR, desk, no chore list!
Terrace/patio

9. 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$917
HK$2,169 total
includes taxes & fees
31 Aug - 1 Sept
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Interior

10. 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, (99 reviews)
"Convenient and comfortable stay"
United States
Cathy G.
The price is HK$1,200
HK$1,905 total
includes taxes & fees
22 Sept - 23 Sept
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Property grounds

11. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (295 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$1,122
HK$2,495 total
includes taxes & fees
7 Sept - 8 Sept
Streamside Cottage Half Mile to Town of Woodstock
Living area

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

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (29 reviews)
"Nice house, on a loud busy street and next door to a bar and close to a busy train track. I wish the host would have answered message questions directly but all I got were pre-written timed responses. Ended up being a good stay with my 18 month old, we enjoyed it."
United States
Brendan F.
The price is HK$953
HK$2,173 total
includes taxes & fees
31 Aug - 1 Sept
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
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$1,570
HK$5,247 total
includes taxes & fees
22 Sept - 23 Sept
Super Comfortable Water-view Home in Saugerties
Living area

14. 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, (28 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.
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Exterior

15. 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, (284 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
The price is HK$1,262
HK$1,702 total
includes taxes & fees
22 Sept - 23 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Outdoor spa tub

16. 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$1,873
HK$3,503 total
includes taxes & fees
26 Aug - 27 Aug
Peaceful Riverfront Cottage with Private Hot tub
Living area

17. 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 HK$2,156
HK$4,768 total
includes taxes & fees
14 Sept - 15 Sept
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Interior

18. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (27 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
Catskill Cottage Walk to Downtown & River Views
Private kitchen

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$797
HK$1,532 total
includes taxes & fees
1 Sept - 2 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Living area

20. 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$2,286
HK$5,572 total
includes taxes & fees
30 Aug - 31 Aug
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
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
"Great spa"
Elizabeth 2-night trip
Posted 5 hours ago
Pocketbook Hotel and Bath

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:

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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 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.