Annandale-on-Hudson Vacation Rentals

Vacation Rentals in Annandale-on-Hudson

The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, 48 reviews
"We thoroughly enjoyed our stay. It was a unique setting. Glen was very accommodating for our check in & out needs. Great location & central to everything we wanted to do & see. Definitely would come back."
The Farm at Hyde Park
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, 199 reviews
"Very clean, just as advertised. The stream behind the cottage is beautiful! Will stay there again if we get a chance to revisit the area. The host was extremely accommodating and available🙂"
The price is $189
$359 total
includes taxes & fees
Jun 17 - Jun 18
Streamside Cottage Walking Distance 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, 38 reviews
"We spent the weekend and had a wonderful time. The property was conveniently located near the center of town while still being very quiet and private. The cottage is perfect for a couple’s weekend getaway. Great spot if you want to have a jumping off point to explore the area. Would definitely stay again."
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Property grounds
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, 22 reviews
"The backyard was really cool! Great features. Beautiful, peaceful, and private. We did not see or hear anyone else on the property during our stay. The apartment was very nice. Cozy, clean and comfortable, perfect for two. The host, Ryan was extremely responsive and friendly. We had an amazing stay would definitely recommend!"
The price is $215
$282 total
includes taxes & fees
Jun 10 - Jun 11
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, 85 reviews
"Everything was as described, instructions to the house were precise and the facility was exactly what we 2 couples) needed for a weekend of strolls in Woodstock and trails around. We cooked 2 dinners, kitchen and BBQ were great."
The price is $111
$303 total
includes taxes & fees
Jun 20 - Jun 21
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very Good, 37 reviews
"Our trip was amazing. We do it again again and again"
The price is $125
$145 total
includes taxes & fees
Jun 9 - Jun 10
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Charming Artist's Retreat
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, 114 reviews
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, 32 reviews
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is $200
$302 total
includes taxes & fees
Jun 10 - Jun 11
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Outdoor spa tub
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
9.6 out of 10, Exceptional, 163 reviews
"The house was fantastic. Close to Hunter Mountain Ski Resort and a cute one street town. Peter and Lara had both wood burning stoves going for us when we arrived. The house is wonderful with a fun separate hang out place for the kids. Well equipped kitchen. Comfortable beds. Hot tub with wonderful views. All the firewood you could ever need. We will be back for sure!"
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, 153 reviews
"We had a great time, and the space was great. The house is so spacious, and that was perfect for us. We would have liked a few more towels, a bit more soap and shampoo, and the grill didn't get hot enough to cook the steak we had brought. Overall a wonderful time. Thank you very much."
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Hamptons on the Hudson in South Saugerties
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, 6 reviews
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Woodstock House on 35 private acres Mtn Views
Woodstock House on 35 private acres Mtn Views
10.0 out of 10, Exceptional, 35 reviews
"Perfect long weekend getaway for our family of four plus our dog. Plenty of room both inside and out. Close to skiing, hikes, and nearby towns, Woostock, Phoenicia, etc. Thank you!"
Woodstock House on 35 private acres Mtn Views
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, 65 reviews
"Very relaxing and enjoyable with excellent views and tranquility!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 71 reviews
"Fantastic, loved everytbing about it"
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Fridge, microwave, oven, stovetop
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
10.0 out of 10, Exceptional, 13 reviews
"We really enjoyed our stay! We had a large group of 24 friends, and the house met all of our needs. It was very clean, had enough bedrooms for everyone, and a large dining table that accommodated everyone for big dinners. We spent a lot of time throughout the weekend outside playing lawn games and sitting by the fire. The place was close enough to grab amenities or go to a grocery store, but off the beaten path and quiet. It was exactly what was listed and made for a where enjoyable time....
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Fridge, microwave, oven, stovetop
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
8.6 out of 10, Excellent, 14 reviews
"There were 26 of us for a nice family gathering. Plenty of bedrooms and beds. Only 2 showers for 26 people a little challenging. Kitchen facilities lacking materials as noted in the listing. Bring your own pots and pans. Hot tub and fire pit were a nice addition. All in all, worked out great."
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Property grounds
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, 41 reviews
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, 31 reviews
"The house is secluded and peaceful with a huge deck for a cool breeze with morning coffee or an evening glass of wine. The house was spotless and well equipped with anything you could possibly need. Restaurants, grocery, and Katterskill Falls for hiking all within a 15-20 minute drive. Our host, Nick, was very attentive making sure everything was as we expected ( and it was). Would stay here again if the opportunity arises. I highly recommend this property for your vacation getaway."
Cozy Relaxing Retreat in Saugerties, NY
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
9.6 out of 10, Exceptional, 42 reviews
"We decided on a trip to Hunter Mountain with our family and some of my sons friends. I came across this house and let me tell you the pictures do not do it justice it’s even better in person!! We were beyond happy with the house and the location…. The house was fully stocked with everything you could imagine. So much room for our group of 13 including our golden retriever! The kids and adults loved the game room some adults even had a Pac-Man competition. We will definitely stay at this house...
LOCATION! Location! Walking distance to Hunter MT! 3rd night 1/2 price w/weekend
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, 8 reviews
"The property was clean and tidy. The manager/owner was very accommodating, responsive and quick. The process of checking in and out was very easy and simple. Location is great as well."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
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See all available properties in Annandale-on-Hudson
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.

Annandale-on-Hudson Vacation Rental Travel Info

Number of vacation rentals
4
Known landmarks
Old Rhinebeck Aerodrome, Center for Performing Arts at Rhinebeck and Museum of Rhinebeck History
International airports
Boston, MA (BOS-Logan Intl.) and Albany, NY (ALB-Albany Intl.)

Other types of properties in Annandale-on-Hudson you may be interested in

Hunter Lodge, a Bluebird by Lark
Lobby sitting area
Hunter Lodge, a Bluebird by Lark
2.5 star property
9.4 out of 10, Exceptional, 389 reviews
"Cozy atmosphere and very convenient location "
The price is $134
$145 total
includes taxes & fees
Jun 17 - Jun 18
Hunter Lodge, a Bluebird by Lark
AutoCamp Catskills
Premium bedding, down comforters, Tempur-Pedic beds, laptop workspace
AutoCamp Catskills
3.5 star property
9.0 out of 10, Wonderful, 277 reviews
"Good"
The price is $218
$280 total
includes taxes & fees
Jul 7 - Jul 8
AutoCamp Catskills
Best Western Plus Kingston Hotel And Conference Center
Lobby
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very Good, 1,006 reviews
"Perfectly pleasant…staff was fun, thoughtful and courteous…room is plenty comfortable and CLEAN. "
The price is $140
$157 total
includes taxes & fees
Jun 23 - Jun 24
Best Western Plus Kingston Hotel And Conference Center
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.

Everything you need to know about Annandale-on-Hudson vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annandale-on-Hudson vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annandale-on-Hudson vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annandale-on-Hudson vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annandale-on-Hudson. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Annandale-on-Hudson in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annandale-on-Hudson rentals

At Expedia, we put the best Annandale-on-Hudson vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Annandale-on-Hudson rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annandale-on-Hudson vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annandale-on-Hudson. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Annandale-on-Hudson?

Yes, you can find vacation rentals near well known local attractions in Annandale-on-Hudson, or you can select a more remote option if you're looking for relaxation. 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 vacation rentals that Annandale-on-Hudson has to offer?

The Farm at Hyde Park: This vacation home rental outside of Annandale-on-Hudson is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 Woodstock Music Shop, or get outside and enjoy nature at Saugerties Village Beach. In the larger area, you’ll find Bard College and Hessel Museum of Art.

What are vacation rentals like in Annandale-on-Hudson?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Annandale-on-Hudson. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

Recent reviews of Annandale-on-Hudson properties
Expedia verified reviews

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

5/5 Excellent
"Great Place and Very Clean "
A verified traveler stayed at Courtyard by Marriott Kingston
Posted 19 hours ago
Courtyard by Marriott Kingston