Annandale-on-Hudson Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Annandale-on-Hudson

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, (261)
"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 HK$1,549
HK$3,017 total
includes taxes & fees
13 Dec - 14 Dec
Streamside Cottage Half Mile to Town of Woodstock
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 HK$973
HK$1,264 total
includes taxes & fees
7 Dec - 8 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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 HK$1,401
HK$2,388 total
includes taxes & fees
28 Dec - 29 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (62)
"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 HK$1,156
HK$1,844 total
includes taxes & fees
4 Jan - 5 Jan 2026
Esopus Creek modern Tiny house Retreat!
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
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, (124)
"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
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan
10.0 out of 10, Exceptional, (54)
"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)
"We had a great time staying at the Washburn Cabin! Plenty of amenities and little touches that made it a pleasant stay, but it still felt like we were unplugged and had plenty of privacy."
United States
Jo P.
Sexiest Lil Cabin in Saugerties, NY
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (44)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is HK$870
HK$1,530 total
includes taxes & fees
7 Dec - 8 Dec
Mid-Century DJ’s Dream
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
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 HK$630
HK$1,787 total
includes taxes & fees
9 Dec - 10 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
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)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is HK$1,170
HK$2,584 total
includes taxes & fees
7 Dec - 8 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
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 HK$6,609
HK$10,543 total
includes taxes & fees
15 Dec - 16 Dec
LOCATION! LOCATION!LOCATION! Luxurious Ski In/Out Jet-Set Condo NEWLY RENOVATED
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
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 HK$1,926
HK$3,813 total
includes taxes & fees
10 Dec - 11 Dec
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Exterior
Beautiful new house 3/4 mile from Hunter Mountain

Beautiful new house 3/4 mile from Hunter Mountain

hunter
9.6 out of 10, Exceptional, (138)
"Really beautiful location with plenty of bedrooms. Very clean!"
United States
Ellen B.
Beautiful new house 3/4 mile from Hunter Mountain
1 bedroom, desk, free WiFi
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook
9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
The price is HK$981
HK$1,682 total
includes taxes & fees
7 Dec - 8 Dec
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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
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

Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

10/10 Excellent
"Front desk was amazing during my checkin time"
Dennis 1-night trip
Posted 6 hours ago
Residence Inn by Marriott Kingston

Find out more about Annandale-on-Hudson

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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?

The Farm at Hyde Park: This holiday home rental outside of Annandale-on-Hudson is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.