Annandale-on-Hudson holiday homes

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

Exceptional

(11 reviews)

Farmette Roquette Hudson Valley

Germantown

8% off

NZ$9,319

for 7 nights, 1 room

NZ$1,331 per night

includes taxes & fees

Exceptional

(90 reviews)

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

Tannersville

9% off

NZ$21,323

for 7 nights, 1 home

NZ$3,046 per night

includes taxes & fees

A beautiful spot for our comfortable cabin

Exceptional

(119 reviews)

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

Bearsville

8% off

NZ$7,473

for 7 nights, 1 cabin

NZ$1,068 per night

includes taxes & fees

Exceptional

(33 reviews)

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Hunter

8% off

NZ$3,102

for 7 nights, 1 chalet

NZ$443 per night

includes taxes & fees

Exceptional

(16 reviews)

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

Hunter

8% off

NZ$5,996

for 7 nights, 1 chalet

NZ$857 per night

includes taxes & fees

Exceptional

(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off

NZ$7,114

for 7 nights, 1 home

NZ$1,016 per night

includes taxes & fees

For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.

A cozy bedroom boasts a unique charm with its stone wall and wide plank flooring. Queen size bed with luxury linens you'll find it hard to leave. For your comfort we installed a MiniSplit system for heating and AC. Creating warm ambiance to enjoy.

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.

Exceptional

(26 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off

NZ$9,315

for 7 nights, 1 home

NZ$1,331 per night

includes taxes & fees

Exceptional

(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off

NZ$21,301

for 7 nights, 1 home

NZ$3,043 per night

includes taxes & fees

Entertainment meets comfort here. Enjoy a movie night on the big screen.

View of the cabin from the road. Sitting on just over an acre of land.

A clean, simple hallway that leads to the downstairs bedroom and bathroom.

Enjoy the view of kitchen activities while hanging out on the couch.

Exceptional

(41 reviews)

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

Catskill

8% off

NZ$4,920

for 7 nights, 1 cabin

NZ$703 per night

includes taxes & fees

Comfortably seats 8 and also doubles as a large board game table.

Whip up delicious meals in the spacious, bright kitchen with ample counter space

View of valley and lush evergreens. Queen bed. Spacious closet

Settle into the many comfy seats in the Family Room.

Exceptional

(40 reviews)

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

Highland

8% off

NZ$10,421

for 7 nights, 1 home

NZ$1,489 per night

includes taxes & fees

stay warm & cozy by the fireplace with large screen TV above

Sit stream side and enjoy the beauty of nature and our (seasonal) fire pit

The fall foliage is gorgeous right in "your own" backyard!!

new, beautiful, fully equipped, large, custom kitchen-plenty of counter space.

Exceptional

(163 reviews)

Sanctuary by the Stream

Phoenicia

13% off

NZ$3,576

for 7 nights, 1 home

NZ$511 per night

includes taxes & fees

Your primary entrance will lead you directly in the homes cool kitchen!

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

8% off

NZ$11,675

for 7 nights, 1 home

NZ$1,668 per night

includes taxes & fees

Exceptional

(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off

NZ$2,778

for 7 nights, 1 unit

NZ$397 per night

includes taxes & fees

Outdoor showers on a hot summer day are the best!

Feel the awe of the 20 foot vaulted ceilings and windows onto the woods

Sitting in the living room area, you feel nestled in the woods.

Exceptional

(20 reviews)

Hudson Valley stunning lake side modern barn in an Enchanted Forest

Clinton Corners

8% off

NZ$6,539

for 7 nights, 1 home

NZ$934 per night

includes taxes & fees

Exceptional

(86 reviews)

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

Ulster Park

8% off

NZ$4,027

for 7 nights, 1 home

NZ$575 per night

includes taxes & fees

Exceptional

(13 reviews)

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

Mount Tremper

12% off

NZ$11,026

for 7 nights, 1 home

NZ$1,575 per night

includes taxes & fees

Exceptional

(128 reviews)

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

Willow

8% off

NZ$4,355

for 7 nights, 1 home

NZ$622 per night

includes taxes & fees

Exceptional

(10 reviews)

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

Lake Hill

8% off

NZ$3,723

for 7 nights, 1 cabin

NZ$532 per night

includes taxes & fees

Exceptional

(10 reviews)

Heart of the Village Victorian Saugerties NY

Saugerties

6% off

NZ$8,471

for 7 nights, 1 home

NZ$1,210 per night

includes taxes & fees

Wonderful

(5 reviews)

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

Maplecrest

8% off

NZ$6,205

for 7 nights, 1 home

NZ$886 per night

includes taxes & fees

Dining leads from kitchen, open view of living room

Exceptional

(52 reviews)

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

Woodstock

12% off

NZ$7,478

for 7 nights, 1 home

NZ$1,068 per night

includes taxes & fees

Exceptional

(27 reviews)

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

Saugerties

8% off

NZ$11,195

for 7 nights, 1 home

NZ$1,599 per night

includes taxes & fees

Exceptional

(39 reviews)

Private Zen Retreat - Near HITS, Hunter, Hiking Trails

Palenville

8% off

NZ$6,745

for 7 nights, 1 home

NZ$964 per night

includes taxes & fees

Exceptional

(12 reviews)

Welcome to The Boathouse! Waterfront/Boats/Hot tub

New Paltz

12% off

NZ$5,340

for 7 nights, 1 home

NZ$763 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Cabin

Cottage

Villa

Chalet

Find properties near top attractions in Annandale-on-Hudson

A grassy field with a brick wall and a large tree with autumn leaves.

Bard College

Find the best place to stay - Annandale-on-Hudson

Premier Host

Sexiest Lil Cabin in Saugerties, NY

Sleeps 2 · 1 bedroom · 1 bathroom

Premier Host

Visit a farm-stay container house on a 30-acre organic forest in Stone Ridge, NY

Sleeps 4 · 2 bedrooms · 1+ bathroom

Cozy Guest Suite At The Blue Ranch

Sleeps 2 · 1 bedroom · 1 bathroom

RIVERFRONT: HITS, Bard, Woodstock, Kingston from spacious enchanting 3 BR house

Sleeps 6 · 3 bedrooms · 1 bathroom

Lovely 1-bedroom apartment with AC in charming Saugerties, 4 minutes to HITS

Sleeps 3 · 1 bedroom · 1 bathroom

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

Sleeps 2 · 1 bedroom · 1 bathroom

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 Bookabach?

Bookabach 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?

Bookabach 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 Bookabach, 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 Bookabach?

To find Annandale-on-Hudson holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?

Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Annandale-on-Hudson to more spacious homes.

What can I expect from Bookabach customer service and Bookabach Care™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?

Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?

Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas

Holiday Rentals

Annandale-on-Hudson holiday homes

Holiday rentals with weekly discounts – Annandale-on-Hudson

Showing deals for:25 Dec - 1 Jan

Farmette Roquette Hudson Valley

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

Secluded Cabin with Hot Tub - 5 Miles to Woodstock

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

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

Secluded family retreat within minutes of Woodstock village

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Church Des Artistes a Hudson Valley retreat

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

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

Sanctuary by the Stream

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

Hudson Valley’s Private Waterfront Camping Getaway

Hudson Valley stunning lake side modern barn in an Enchanted Forest

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

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

Waterfront Mid-century Modern Gem Surround by Forever Wild Land

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

Heart of the Village Victorian Saugerties NY

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

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

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

Private Zen Retreat - Near HITS, Hunter, Hiking Trails

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Find spaces that suit your style

Find properties near top attractions in Annandale-on-Hudson

Bard College

Find the best place to stay - Annandale-on-Hudson

Sexiest Lil Cabin in Saugerties, NY

Visit a farm-stay container house on a 30-acre organic forest in Stone Ridge, NY

Cozy Guest Suite At The Blue Ranch

RIVERFRONT: HITS, Bard, Woodstock, Kingston from spacious enchanting 3 BR house

Lovely 1-bedroom apartment with AC in charming Saugerties, 4 minutes to HITS

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

Peace of mind

More quality time

All the privacy of home

More for less

Travel to arty Annandale-on-Hudson

Sightseeing in and around Annandale-on-Hudson

Exploring the natural features in Annandale-on-Hudson

Travelling to and around Annandale-on-Hudson

Frequently asked questions

More holiday ideas