Default HTG hotel image

Annandale-on-Hudson Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Annandale-on-Hudson vacation rentals

Coffee/tea maker, fridge, microwave, oven

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.
$239 nightly
The price is $268
Jul 28 - Jul 29
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Exterior

'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, (47 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
Jul 26 - Jul 27
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
1 bedroom, desk, WiFi (free), bed sheets

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.
$263 nightly
The price is $298
Jul 28 - Jul 29
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Interior

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, (11 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
$222 nightly
The price is $249
Jul 28 - Jul 29
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Interior

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.
$274 nightly
The price is $307
Aug 18 - Aug 19
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
Terrace/patio

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, (32 reviews)
"The beds were especially comfortable! "
United States
josh p.
$226 nightly
The price is $253
Jul 27 - Jul 28
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Interior

Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (16 reviews)
"The apartment was very clean and updated! Small back deck was nice to drink my morning coffee! Only issue was kids yelling and screaming in the neighborhood till almost 11pm."
United States
Donna
$238 nightly
The price is $267
Aug 3 - Aug 4
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
Private kitchen

Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (5 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
$181 nightly
The price is $203
Jul 27 - Jul 28
Total with taxes and fees
Woods Cabin-Kingston/Woodstock, NY.
Interior

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, (93 reviews)
"Wonderful stay. "
United States
Chris L.
$201 nightly
The price is $225
Aug 9 - Aug 10
Total with taxes and fees
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Smart TV

Hot Tub - Fire Pit - BBQ - Hammock - Colonial

Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Kingston
9.6 out of 10, Exceptional, (28 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.
$252 nightly
The price is $282
Jul 28 - Jul 29
Total with taxes and fees
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (289 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
$278 nightly
The price is $312
Jul 26 - Jul 27
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
2 bedrooms, desk, WiFi (free), bed sheets

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
$325 nightly
The price is $364
Aug 18 - Aug 19
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
Exterior

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, (260 reviews)
"The experience was wonderful. Great and peaceful place."
United States
Seung Jae
$209 nightly
The price is $226
Aug 24 - Aug 25
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Living area

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, (25 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.
$420 nightly
The price is $475
Aug 23 - Aug 24
Total with taxes and fees
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Outdoor spa tub

Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub
Lake Katrine
10.0 out of 10, Exceptional, (14 reviews)
"We had a wonderful stay! The space was beautifully organized, with thoughtful touches and everything clearly labeled. It was spotless, the beds were incredibly comfortable, and the location was lovely. Every detail was considered, and we’re already planning our return!"
United States
Elaine V.
$372 nightly
The price is $416
Jul 26 - Jul 27
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
Living area

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.
$635 nightly
The price is $711
Jul 26 - Jul 27
Total with taxes and fees
Hot Tub; Big Kitchen; 2 Blocks to Downtown Saugerties
Coffee/tea maker, fridge, oven, stovetop

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (5 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
$185 nightly
The price is $210
Aug 5 - Aug 6
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Interior

3BR Farmhouse in the Village of Saugerties - Walk to it all! 5 min drive to HITS

3BR Farmhouse in the Village of Saugerties - Walk to it all! 5 min drive to HITS
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Great location, very well-stocked. Would absolutely stay here again."
United States
Kristen R.
$440 nightly
The price is $493
Aug 12 - Aug 13
Total with taxes and fees
3BR Farmhouse in the Village of Saugerties - Walk to it all! 5 min drive to HITS
Smart TV, fireplace

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
$539 nightly
The price is $604
Aug 3 - Aug 4
Total with taxes and fees
Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (5 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$453 nightly
The price is $507
Jul 27 - Jul 28
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
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

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

10/10 Excellent
"Loved the plus of the laundry amenities !!"
tatiana 1-night trip
Posted 9 hours ago
Holiday Inn Express & Suites Kingston-Ulster by IHG

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 Clermont State Historic Site. 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.