Annandale-on-Hudson holiday rentals

We found 1,554 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Annandale-on-Hudson that are perfect for your trip. Whether you're staying in a holiday rental with friends, family or even just your pets, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Annandale-on-Hudson

Showing deals for:25 Dec - 1 Jan

Interior
Interior
Private kitchen
Property grounds
Exceptional
(11 reviews)

Farmette Roquette Hudson Valley

Germantown

8% off
AU$7,372
for 7 nights, 1 room
AU$1,053 per night
includes taxes & fees
Farmette Roquette Hudson Valley
Kitchen
Hot tub
Sunroom
Fully finished attic: full size bed
Exceptional
(90 reviews)

Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!

Tannersville

9% off
AU$17,089
for 7 nights, 1 home
AU$2,441 per night
includes taxes & fees
Start thinking about Fall Foliage! Hot tub, fabulous kitchen, views everywhere!
Our Sunny Living Room with Wood Stove
Rear Deck, Hot Tub and Screened Porch
Open kitchen.
Property grounds
Exceptional
(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off
AU$5,809
for 7 nights, 1 cabin
AU$830 per night
includes taxes & fees
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Interior
Exterior
Terrace/patio
Living area
Exceptional
(34 reviews)

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

8% off
AU$2,463
for 7 nights, 1 chalet
AU$352 per night
includes taxes & fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Private kitchen
Exterior
Living area
Living area
Exceptional
(16 reviews)

Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates

Hunter

8% off
AU$4,716
for 7 nights, 1 chalet
AU$674 per night
includes taxes & fees
Cozy A FRAME ski retreat, walking distance into Hunter Mountain. New 2026 Rates
Private kitchen
Exterior
Pool
Outdoor dining
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
AU$5,635
for 7 nights, 1 home
AU$805 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
A Special Place for Your Special Times! 4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
Dining
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Exceptional
(26 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$7,491
for 7 nights, 1 home
AU$1,070 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
Front Entry
Outdoor dining
Interior
Exterior detail
Exceptional
(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off
AU$17,570
for 7 nights, 1 home
AU$2,510 per night
includes taxes & fees
Church Des Artistes a Hudson Valley retreat
Living area
View of the cabin from the road. Sitting on just over an acre of land.
Enjoy the view of kitchen activities while hanging out on the couch.
Entertainment meets comfort here. Enjoy a movie night on the big screen.
Exceptional
(41 reviews)

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

Catskill

8% off
AU$3,924
for 7 nights, 1 cabin
AU$561 per night
includes taxes & fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Settle into the many comfy seats in the Family Room.
Whip up delicious meals in the spacious, bright kitchen with ample counter space
View of valley and lush evergreens. Queen bed. Spacious closet
Sit together outside, enjoy fresh Hudson Valley air, share stories and memories
Exceptional
(40 reviews)

Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz

Highland

8% off
AU$8,341
for 7 nights, 1 home
AU$1,192 per night
includes taxes & fees
Beautiful Home - 4BR/2.5BA - Hot tub and Patio - Minutes from New Paltz
The fall foliage is gorgeous right in "your own" backyard!!
Sit stream side and enjoy the beauty of nature and our (seasonal) fire pit
bluestone, more shaded patio with shade garden
new, beautiful, fully equipped, large, custom kitchen-plenty of counter space.
Exceptional
(163 reviews)

Sanctuary by the Stream

Phoenicia

13% off
AU$2,886
for 7 nights, 1 home
AU$412 per night
includes taxes & fees
Sanctuary by the Stream
130 year old stone fireplace in green living room
Your primary entrance will lead you directly in the homes cool kitchen!
Interior
Kitchen comes fully stocked with pots/pans, dishes, silverware, glasses, etc.
Exceptional
(88 reviews)

Featured on MTV ! You Have To See It To Believe It ! Unlike any other !

Haines Falls

9% off
AU$9,223
for 7 nights, 1 home
AU$1,318 per night
includes taxes & fees
Featured on MTV ! You Have To See It To Believe It ! Unlike any other !
Property grounds
Property grounds
Room
Property grounds
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,231
for 7 nights, 1 unit
AU$319 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
It's mesmerizing to watch and hear the roaring waterfall from this bridge.
Feel the awe of the 20 foot vaulted ceilings and windows onto the woods
The Enchanted Forest beckons!
Outdoor showers on a hot summer day are the best!
Exceptional
(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off
AU$5,171
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Hudson Valley stunning lake side modern barn in an Enchanted Forest
Property grounds
Room
Dining
Interior
Exceptional
(86 reviews)

for the creative spirit, swimming dock on pond, horses to pet, Fire pit

Ulster Park

8% off
AU$3,224
for 7 nights, 1 home
AU$461 per night
includes taxes & fees
for the creative spirit, swimming dock on pond, horses to pet, Fire pit
Living area
Property grounds
Living area
Private kitchen
Exceptional
(13 reviews)

"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres

Mount Tremper

12% off
AU$8,718
for 7 nights, 1 home
AU$1,245 per night
includes taxes & fees
"Frank Lloyd Wright" Catskills Mountain Yoga-Spa Retreat on 15 Acres
Cooking is a breeze in this recently remodeled kitchen
Welcome to Bridge House
Large sliders bring nature indoors
Fern garden in summer
Exceptional
(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off
AU$3,490
for 7 nights, 1 home
AU$499 per night
includes taxes & fees
Waterfront Mid-century Modern Gem Surround by Forever Wild Land
Private kitchen
Exterior
Property grounds
Living area
Exceptional
(10 reviews)

Most Charming, Most quiet place in the Catskills--Willow-brook Cottage

Lake Hill

8% off
AU$3,006
for 7 nights, 1 cabin
AU$429 per night
includes taxes & fees
Most Charming, Most quiet place in the Catskills--Willow-brook Cottage
Living area
Exterior detail
Room
Interior
Exceptional
(10 reviews)

Heart of the Village Victorian Saugerties NY

Saugerties

6% off
AU$6,765
for 7 nights, 1 home
AU$966 per night
includes taxes & fees
Heart of the Village Victorian Saugerties NY
Room
Exterior
Private kitchen
Living area
Wonderful
(5 reviews)

Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet

Maplecrest

8% off
AU$4,901
for 7 nights, 1 home
AU$700 per night
includes taxes & fees
Newly Renovated House ~ Secluded 5 Acre Retreat ~ Peaceful and Quiet
Exterior
Private kitchen
Dining leads from kitchen, open view of living room
Great room featuring a wonderful wall of windows
Exceptional
(53 reviews)

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock

12% off
AU$5,931
for 7 nights, 1 home
AU$847 per night
includes taxes & fees
Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres
Welcome!!
Interior
Living area
Great Room/Kitchen Area
Exceptional
(27 reviews)

Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals

Saugerties

8% off
AU$8,870
for 7 nights, 1 home
AU$1,267 per night
includes taxes & fees
Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals
Exterior
Living area
Living area
Private kitchen
Exceptional
(39 reviews)

Private Zen Retreat - Near HITS, Hunter, Hiking Trails

Palenville

8% off
AU$5,378
for 7 nights, 1 home
AU$768 per night
includes taxes & fees
Private Zen Retreat - Near HITS, Hunter, Hiking Trails
Living area
Living area
Living area
Living area
Exceptional
(12 reviews)

Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz

12% off
AU$4,193
for 7 nights, 1 home
AU$599 per night
includes taxes & fees
Welcome to The Boathouse! Waterfront/Boats/Hot tub

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to arty Annandale-on-Hudson

Take a holiday to Annandale-on-Hudson and enjoy the area's art galleries, history and museums. One of the city's many top draws is its university setting. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Annandale-on-Hudson

Are you searching for things to do while you're in the area? Venture out of your holiday home and check out everything that makes Annandale-on-Hudson a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Indian Head Mountain (12.6 mi / 20.2 km)
  • Kaaterskill Falls (14.2 mi / 22.9 km)
  • Mountain Trails Cross Country Ski and Snowshoe Center (16.9 mi / 27.3 km)
  • Red Hook Golf Club (5.1 mi / 8.3 km)
  • Woodstock Golf Club (10.3 mi / 16.7 km)

Exploring the natural features in Annandale-on-Hudson

Whether you're an active traveller or just want to take in the scenery, Annandale-on-Hudson is a great place to get out in nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Falling Waters Preserve (2.8 mi / 4.5 km)
  • Saugerties Village Beach (4 mi / 6.5 km)
  • Opus 40 (6.6 mi / 10.6 km)
  • Kingston Point Beach (6.9 mi / 11.2 km)
  • Esopus Creek (8 mi / 12.9 km)
  • Ashokan Rail Trail- Woodstock Dike Trailhead (9.6 mi / 15.4 km)

Travelling to and around Annandale-on-Hudson

The nearest airport is in Hudson, NY (HCC-Columbia County), located 21.4 mi (34.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Annandale-On-Hudson when booking a holiday rental?
When considering a holiday rental in Annandale-On-Hudson, one of the most appealing areas is the neighbourhood surrounding Bard College. This picturesque locale not only offers a vibrant arts and culture scene but also boasts stunning views of the Hudson River. Staying here puts you in close proximity to the college's various cultural events and performances, making it a delightful choice for those interested in the arts.Another attractive area is the nearby village of Tivoli, which features charming streets lined with quaint shops and eateries. Tivoli is known for its lovely community vibe and hosts some delightful dining options, great for sampling local cuisine. You'll also find the scenic Tivoli Bays, a lovely spot for nature walks and birdwatching.In terms of available holiday rentals, the region offers a diverse selection, suiting various tastes and budgets. Whether you prefer a cosy cottage or a more modern apartment, you are likely to find a suitable property that provides a comfortable base for exploring this beautiful part of New York.
When is the best time to visit Annandale-On-Hudson for a holiday rental?
The best time to visit Annandale-On-Hudson is during September, when the vibrant fall season begins to unfold. This month marks the tail end of the peak travel season, which spans from July to September, attracting those eager to experience the picturesque landscapes and cultural offerings of the area.As summer wanes, visitors can enjoy comfortable temperatures typically ranging from 10 to 25 degrees Celsius, ideal for outdoor activities such as hiking and exploring the beautiful surroundings. September is particularly charming, with the foliage starting to hint at autumn colours, providing a stunning backdrop for leisurely strolls and sightseeing.For those looking for a more budget-friendly option, December offers a lovely, quiet atmosphere superb for a winter getaway. While this is the low season, the charm of the Hudson Valley during the holidays, with its festive decorations and serene landscapes, creates a great experience that shouldn't be missed.
What are the top attractions in Annandale-On-Hudson?
In Annandale-On-Hudson, visitors can explore a variety of attractions that highlight the area's cultural and natural beauty. The most popular site is Bard College, which not only offers beautiful campus grounds but also hosts the Fisher Centre for the Performing Arts, where one can attend various performances and events throughout the year.Nearby, the picturesque landscape along the Hudson River provides opportunities for scenic walks and outdoor activities, with views that are especially stunning during the fall foliage season.The area also features the historic Montgomery Place, a former estate now part of the Bard College campus, which includes lovely gardens and walking paths. Visitors can enjoy art exhibitions at the Bard College Centre for Curatorial Studies and Art in the nearby Red Hook area, further enriching the cultural experience of the region.
Are all fees included in the Annandale-on-Hudson holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Annandale-on-Hudson holiday homes with parking?
Stayz offers a wide selection of holiday homes in Annandale-on-Hudson with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Annandale-on-Hudson holiday homes?
You can find great discounts on holiday homes in Annandale-on-Hudson on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Annandale-on-Hudson holiday home booking on Stayz?
To find Annandale-on-Hudson holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Annandale-on-Hudson?
A long-stay holiday home in Annandale-on-Hudson is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Annandale-on-Hudson holiday home?
Book your Annandale-on-Hudson holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Annandale-on-Hudson?
Prices for holiday homes in Annandale-on-Hudson vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Annandale-on-Hudson to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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