Holiday Rentals in Annandale-on-Hudson

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday 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.
The price is €145
includes taxes & fees
30 Nov - 1 Dec
'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)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park
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)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
The price is €345
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is €174
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
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)
"Enjoyed our stay!"
United States
Mike T.
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)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is €278
includes taxes & fees
30 Nov - 1 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
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
The price is €235
includes taxes & fees
25 Nov - 26 Nov
Esopus Creek modern Tiny house Retreat!
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan
10.0 out of 10, Exceptional, (52)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"A little piece of paradise!"
United States
Christi 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
The price is €130
includes taxes & fees
30 Nov - 1 Dec
Sioux Tipi on Chloe's Lake
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.
The price is €225
includes taxes & fees
1 Dec - 2 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Fridge, microwave, oven, stovetop
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend

Hunter
9.6 out of 10, Exceptional, (51)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
United States
Chris S.
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
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.
The price is €293
includes taxes & fees
30 Nov - 1 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend

Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend

Hunter
9.6 out of 10, Exceptional, (77)
"House was very clean. Property managers were very responsive to check in and check out time and anything we needed during our stay. Very close to the mountain and beautiful location. Would highly recommend."
United States
Jamie M.
Heart of Hunter Village; across MT!Spring Special3rd night half OFF!” W/weekend
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)
"The cabin is beautiful,clean and private all the amenities are there and if you feel like venturing out the town of Woodstock is close by "
United States
Edward C.
The price is €440
includes taxes & fees
25 Nov - 26 Nov
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
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)
"Loved our stay! Highly recommend this property! It was so peaceful and relaxing! The pool was the perfect size and everything was so clean and well maintained. We'll definitely will be going back soon! "
United States
Heidi C.
Secluded family retreat within minutes of Woodstock village
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)
"great property with lots of play/sleep/eat options for a large family. Loved mornings and nights on the large screened porch---our favorite spot. nice proximity to the town of Woodstock ."
United States
Jo C.
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.
The price is €1,367
includes taxes & fees
25 Nov - 26 Nov
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
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

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent
"Hotel was beautiful and spacious. Felt like a luxury hotel."
Lee 1-night trip
Posted 2 days ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

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, apart-hotels, 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 €130 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!: This holiday home rental outside of Annandale-on-Hudson is located on a river, and has a fireplace, a BBQ 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 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 Kiwanis Ice Arena, 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.