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Annandale-on-Hudson Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Annandale-on-Hudson vacation rentals

Coffee/tea maker, fridge, microwave, oven

1. 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.
$220 nightly
The price is $246
Sep 8 - Sep 9
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Interior

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

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
$236 nightly
The price is $264
Sep 23 - Sep 24
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & 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
8.0 out of 10, Very Good, (51 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.
$133 nightly
The price is $148
Sep 9 - Sep 10
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Interior

4. 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, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$231 nightly
The price is $259
Sep 9 - Sep 10
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
1 bedroom, desk, WiFi (free), 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, (32 reviews)
"great place for homebase to visit Hudson Valley area and host was very communicative and helpful"
United States
Brian C.
$280 nightly
The price is $316
Sep 8 - Sep 9
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Interior

6. 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.
$238 nightly
The price is $267
Sep 9 - Sep 10
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
Classic Tent, Garden View | Outdoor dining

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
$222 nightly
The price is $248
Sep 7 - Sep 8
Total with taxes and fees
Gatherwild Ranch
Terrace/patio

8. 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)
"Clean, host answered in timely fashion and provided accommodations if needed or requested. Great stay overall!"
United States
Erin H.
$250 nightly
The price is $280
Sep 17 - Sep 18
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Coffee/tea maker, paper towels

9. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.4 out of 10, Exceptional, (10 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
$180 nightly
The price is $202
Sep 3 - Sep 4
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
2 bedrooms, desk, WiFi (free), bed sheets

10. 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
$300 nightly
The price is $336
Sep 15 - Sep 16
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
1 bedroom, WiFi (free), bed sheets

11. Soft Launch Deal: Butterfly Bungalow Studio

Soft Launch Deal: Butterfly Bungalow Studio
Saugerties
$196 nightly
The price is $219
Sep 15 - Sep 16
Total with taxes and fees
Soft Launch Deal: Butterfly Bungalow Studio
Exterior

12. 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, (290 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
$199 nightly
The price is $215
Sep 3 - Sep 4
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Smart TV

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

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (31 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.
$230 nightly
The price is $258
Sep 10 - Sep 11
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Interior

14. 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.
$218 nightly
The price is $244
Sep 3 - Sep 4
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Dining

15. 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.
$560 nightly
The price is $627
Sep 14 - Sep 15
Total with taxes and fees
Super Comfortable Water-view Home in Saugerties
Property grounds

16. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (296 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 traveler
$272 nightly
The price is $305
Sep 7 - Sep 8
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Coffee/tea maker, fridge, oven, stovetop

17. 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.
$180 nightly
The price is $204
Sep 15 - Sep 16
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Outdoor spa tub

18. Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (15 reviews)
"A nice relaxing spot."
United States
Darren F.
$362 nightly
The price is $406
Sep 3 - Sep 4
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
Outdoor dining

19. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (25 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$316 nightly
The price is $354
Sep 3 - Sep 4
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Dining

20. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (16 reviews)
"We had never stayed overnight on a boat before and were a little nervous. Now we can't wait to stay on one again! Melissa and AJ were so accommodating and extremely nice....perfect place to stay if seeing a concert at Catskill Point. They dropped us off at concert and picked us up on pontoon - how fun is that? To wake up to a sunny and serene morning while having coffee on the creek was priceless. I never do reviews but felt compelled to do this one only because if you are having...
United States
Frances K.
$235 nightly
The price is $263
Sep 3 - Sep 4
Total with taxes and fees
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"Clean room. Could use some updating . Smelled musty. Sherry in a decanter was a nice touch after stumbling through dark parking lot to find an overgrown walkway. Best part was the town .. adorable ! Lined with cute boutiques and all types of places to eat Def had quite a historic vibe. The overall area is stunning and quite picturesque.!"
Lori 2-night trip
Posted 13 hours ago
Beekman Arms and Delamater Inn

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 $148 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.

Explore a world of travel with Expedia

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?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This vacation home rental outside of Annandale-on-Hudson is located on a river and has a fireplace, a patio, and a barbecue grill 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 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 Saugerties Village Beach. 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.