Annandale-on-Hudson Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
10 Jul - 11 Jul
Tomorrow
11 Jul - 12 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Annandale-on-Hudson

Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.0 out of 10, Wonderful, (30)
"Great place "
The price is NZ$421
includes taxes & fees
27 July - 28 July
Postcard Cabins Eastern Catskills
The Farm at Hyde Park
Exterior

The Farm at Hyde Park

9.8 out of 10, Exceptional, (71)
"We were visiting the Culinary Institute highly recommend it."
The Farm at Hyde Park
Esopus Creek modern Tiny house Retreat!
Outdoor dining

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (37)
"Had a fantastic stay for a quick overnight trip to ski."
The price is NZ$402
includes taxes & fees
16 July - 17 July
Esopus Creek modern Tiny house Retreat!
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties
'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, (42)
"Perfect place to reconnect with natural world and yourself"
The price is NZ$271
includes taxes & fees
23 July - 24 July
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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 NZ$243
includes taxes & fees
13 July - 14 July
Sioux Tipi on Chloe's Lake
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Children's area

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is NZ$521
includes taxes & fees
13 July - 14 July
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Private kitchen

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is NZ$385
includes taxes & fees
14 July - 15 July
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
3 bedrooms, iron/ironing board, WiFi, bed sheets

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (175)
"We loved our stay at this home! It is full of so much light and good vibes. We planned the weekend around a concert at Levon Helms studio, which was right down the street. The owners/management were wonderful & easy to get in touch with (not that we needed anything). The deck & music room were enjoyed the most :)"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
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, (88)
"Great place in the woods!"
Totally secluded Yurt surrounded by waterfalls, brooks, cliffs and forest
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, (88)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
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, (16)
"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
A-Frame of Mind
Exterior

A-Frame of Mind

10.0 out of 10, Exceptional, (58)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (241)
"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."
Streamside Cottage Half Mile to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Exterior

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (65)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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, (127)
"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
The Chicken Coop
Outdoor dining

The Chicken Coop

8.0 out of 10, Very good, (3)
"Very cool place everything u need is just a short drive away "
The Chicken Coop
Cozy Modern Studio Apt in Glasco
Interior

Cozy Modern Studio Apt in Glasco

2.0 out of 10, (2)
"I reserved this property and then received a cryptic message stating it was not available for the days I booked. However, the owner never gave a refund and has not responded to messages from me or VRBO. Beware of phony listings!"
The price is NZ$329
includes taxes & fees
11 July - 12 July
Cozy Modern Studio Apt in Glasco
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The Tiny Nook is as cute and charming as the listing suggests, and came well equipped for a short getaway. It was easy to find, quiet, and felt secluded, even as the leaves were falling. The hosts were also very responsive and had some great recommendations of nearby places to visit. "
The price is NZ$700
includes taxes & fees
13 July - 14 July
Modern Luxurious Cabin, Catskills - The Tiny Nook
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
1 bedroom, desk, WiFi

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

10.0 out of 10, Exceptional, (1)
"We were in town for a wedding and needed a spot close to the farm. This spot was a gem. Tucked away, quiet and clean - my husband, dog and I had a great stay. We were only able to stay for a night but I wish we could have stayed a bit longer. This is a really cute community with nice things to see and do. The host is amazing! We’re so grateful to her. "
The price is NZ$407
includes taxes & fees
13 July - 14 July
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 Trolley Museum of New York, 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.