Annandale-on-Hudson Vacation Rentals

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Vacation Rentals in Annandale-on-Hudson

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
8.2 out of 10, Very Good, (46)
"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.
$145 nightly
The price is $162
Nov 19 - Nov 20
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (85)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
United States
Robert W.
The Farm at Hyde Park
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"The entire process and stay were flawless. We had a rush booking and every request we had was accommodated. I give the highest recommendation and will hopefully being staying here again."
United States
Gordon V.
Hamptons on the Hudson in South Saugerties
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons

A Spectacular 50 Mile View of the Hudson Valley in all seasons

Saugerties
9.8 out of 10, Exceptional, (95)
"Had my mother in law and sister in law in town and booked them this adorable place with an amazing view close to town. "
United States
Emily K.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Children's area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

woodstock
9.0 out of 10, Wonderful, (45)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
United States
Paul H.
$280 nightly
The price is $314
Nov 23 - Nov 24
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Great place to stay! Close to many attractions by car - most 10-15 minutes. Clean and comfortable. Kevin has lots of great suggestions on places to go and restaurants."
United States
Anonymous traveler
$173 nightly
The price is $196
Nov 18 - Nov 19
Total with taxes and fees
Mid-Century DJ’s Dream
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, (259)
"Very cozy cottage with everything you need, close to town, and a beautiful stream right in the backyard that we loved listening to."
United States
Kevin M.
Streamside Cottage Half Mile to Town of Woodstock
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
$215 nightly
The price is $240
Nov 17 - Nov 18
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Bearsville
10.0 out of 10, Exceptional, (123)
"As roomy as promised, and one of the quietest places I've ever been. May return for our annual gathering next year."
United States
Tony G.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
United States
Julie L.
Sexiest Lil Cabin in Saugerties, NY
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
$130 nightly
The price is $146
Nov 17 - Nov 18
Total with taxes and fees
Sioux Tipi on Chloe's Lake
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

Hunter
9.4 out of 10, Exceptional, (50)
"Recently re-modeled house that is located very close to the mountain. The house was very nice, and has a nice 'ski house' feel to it, complete with a hot tub on the back porch. Overall, I would highly recommend this place to anyone looking for a place in the area."
United States
Christopher C.
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Catskill
9.8 out of 10, Exceptional, (33)
"Great location "
United States
steve p.
$307 nightly
The price is $332
Nov 18 - Nov 19
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
$215 nightly
The price is $241
Nov 17 - Nov 18
Total with taxes and fees
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan
10.0 out of 10, Exceptional, (52)
"Nice place. Beautiful seroundings"
United States
Pierre B.
Relaxing Catskill Mountain Cottage.
Smart TV
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC

Mt. Tremper
9.6 out of 10, Exceptional, (10)
"Definitely will be back! Thanks for an amazing stay, place is really fabulous, clean and kept at super shape. All small and big things are there, just park and get in. Lovely!"
United States
Alon R.
$438 nightly
The price is $490
Nov 20 - Nov 21
Total with taxes and fees
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Exterior
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Woodstock
10.0 out of 10, Exceptional, (116)
"The owners were very easy to communicate with. Lots of room for everyone. The pool and hot tub were big hits!"
United States
Laurie M.
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Exterior
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED

Hunter Highlands
10.0 out of 10, Exceptional, (10)
"We loved staying at this condo. The location was amazing for back and forth to the slopes it was so easy! The beds were so comfortable and the house was clean! Communication with the owner was excellent. We will definitely stay again! "
United States
Melissa B.
$1,421 nightly
The price is $1,535
Nov 17 - Nov 18
Total with taxes and fees
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
Property grounds
Many perfect sunsets at the magical house on the lake

Many perfect sunsets at the magical house on the lake

Ulster Park
9.8 out of 10, Exceptional, (141)
"Had a great time. The house was clean and the lake was gorgeous! "
United States
Arthur S.
Many perfect sunsets at the magical house on the lake
Outdoor dining
Secluded family retreat within minutes of Woodstock village

Secluded family retreat within minutes of Woodstock village

Woodstock
10.0 out of 10, Exceptional, (47)
"A beautiful, clean house that came as advertised. We spent a lot of time out and about but enjoyed whenever we were at the house."
United States
Patrick F.
Secluded family retreat within minutes of Woodstock village
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

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

10/10 Excellent
"It was great!! Would definitely recommend! Loved the pool and hot tub. Everything was clean. "
Rebecca 1-night trip
Posted 1 day ago
Courtyard by Marriott Kingston

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 $146 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!: This vacation home rental outside of Annandale-on-Hudson is located on a river and has a fireplace, a barbecue grill, and air-conditioning 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 Kiwanis Ice Arena, or get outside and enjoy nature at Falling Waters Preserve. 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.