Annandale-on-Hudson Holiday Rentals

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1 Sept - 2 Sept
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2 Sept - 3 Sept
This weekend
5 Sept - 7 Sept
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12 Sept - 14 Sept

Holiday Rentals in Annandale-on-Hudson

Our top choices for Annandale-on-Hudson holiday rentals

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.4 out of 10, Exceptional, (67)
"Really beautiful place to enjoy nature with family!!"
The price is HK$1,084
HK$1,465 total
includes taxes & fees
2 Sept - 3 Sept
Postcard Cabins Eastern Catskills
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (46)
"Perfect place to reconnect with natural world and yourself"
The price is HK$974
HK$1,266 total
includes taxes & fees
3 Sept - 4 Sept
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (76)
"We enjoyed our stay...lots to do in the area. Glen was very friendly and accommodating. "
The Farm at Hyde Park
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Exterior

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

9.8 out of 10, Exceptional, (92)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior

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

9.8 out of 10, Exceptional, (27)
"Great location "
The price is HK$1,193
HK$2,618 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children’s area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is HK$1,403
HK$2,419 total
includes taxes & fees
7 Sept - 8 Sept
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Jessie's Harvest House
Bar (on property)

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is HK$842
HK$1,493 total
includes taxes & fees
2 Sept - 3 Sept
Jessie's Harvest House
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (50)
"We stayed one night, and it was great! We met one of the owners too. He was very nice and helpful. The property was neat and clean. It has one bedroom, one loft bedroom area, and one pull out couch. We really enjoyed our stay!"
The price is HK$1,158
HK$1,873 total
includes taxes & fees
2 Sept - 3 Sept
Esopus Creek modern Tiny house Retreat!
Sexiest Lil Cabin in Saugerties, NY
Exterior

Sexiest Lil Cabin in Saugerties, NY

9.0 out of 10, Wonderful, (12)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (250)
"A beautiful quiet setting! "
The price is HK$1,162
HK$2,523 total
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Outdoor pool

NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool

10.0 out of 10, Exceptional, (131)
"Stunning views, lovely house and pool, large kitchen, well equipped. Very responsive owner. Strongly recommend for family. "
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Sioux Tipi on Chloe's Lake
Exterior

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is HK$858
HK$1,135 total
includes taxes & fees
7 Sept - 8 Sept
Sioux Tipi on Chloe's Lake
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (132)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain
Charming Yacht on Catskill Creek
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Charming Yacht on Catskill Creek

9.8 out of 10, Exceptional, (8)
"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "
The price is HK$1,017
HK$1,739 total
includes taxes & fees
3 Sept - 4 Sept
Charming Yacht on Catskill Creek
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
2 bedrooms, iron/ironing board, WiFi, bed sheets

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
1 bedroom, travel cot, free WiFi, bed sheets

Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest

10.0 out of 10, Exceptional, (92)
"We loved this stay! The yurt was absolutely charming! Such an amazing location within easy distance of hiking and the Empire State Trail bicycle path, plus great dining in New Paltz and Kingston."
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
TV, fireplace, books

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (29)
"Six of us stayed at the Sleepy Hollow Lake in Athens for a girls trip and it was the PERFECT location! Not far from town, amazing views, and a hot tub overlooking mountains. Diana’s communication during our stay were top notch. Would love to stay again! "
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Exterior

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

10.0 out of 10, Exceptional, (113)
"Amazing Woodstock location!"
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
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

Find out more about Annandale-on-Hudson

Find out more about Annandale-on-Hudson

Search for holiday rentals in Annandale-on-Hudson on Expedia! You can easily find your home rentals, villas, holiday apartments in Annandale-on-Hudson using one of the methods below:

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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?

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.