Woodstock Vacation Rentals

Vacation Rentals in Woodstock

Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is $169
$333 total
includes taxes & fees
Jun 3 - Jun 4
Streamside Cottage Walking Distance to Town of Woodstock
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (153)
"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!
Exterior
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
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Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is $180
$279 total
includes taxes & fees
Jun 2 - Jun 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (48)
"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
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)
"Our trip was amazing. We do it again again and again"
The price is $125
$145 total
includes taxes & fees
May 26 - May 27
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior
Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (229)
"Good for the price. "
The price is $125
$140 total
includes taxes & fees
May 23 - May 24
Starlite Motel
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (82)
"Very clean home. Had everything we needed. Quiet location. All beds were extremely comfortable. Host was very helpful and quick to reply. Good location that was close to area attractions. Would definitely look to stay here again! Thank you Cristiana!"
The price is $124
$318 total
includes taxes & fees
Jun 20 - Jun 21
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Fridge, microwave, oven, stovetop
Charming Artist's Retreat
10.0 out of 10, Exceptional, (113)
"From beginning to end a pleasant stay. Owner was on contact to make sure everything was in order. Fresh cut flowers, plenty of clean white fluffy towels, comfortable bedding and the view through sparkling clear windows. What a wonderful way to spend the mother's day weekend with my daughter and spend some time outdoors exploring little Hudson river towns. 10 thumbs up!!!!"
Charming Artist's Retreat
Outdoor dining
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
Terrace/patio
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
10.0 out of 10, Exceptional, (7)
"House and location were great, would definitely come back."
Best Mountain Views Triple level Deck /w Hot tub Brand New Home Sleeps 30!
Exterior
Beautiful House 0,5 Mile From Hunter Mountain
9.8 out of 10, Exceptional, (188)
"It was a great family time. Play and rest"
Beautiful House 0,5 Mile From Hunter Mountain
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"An unassuming setting belies the well-appointed interior and thoughtful extras you’ll find within. Parking is tight but it is off-street and the location offers come-and-go convenience for exploring the area."
The price is $104
$233 total
includes taxes & fees
Jun 2 - Jun 3
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds
Updated Cabin on the Esopus
10.0 out of 10, Exceptional, (17)
"The cabin was excellent, very clean, and they gave us everything we needed"
Updated Cabin on the Esopus
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
Property grounds
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~Mother's Day on the Mountain~2 hrs to NYC ULTIMATE PRIVACY!
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
Property grounds
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (208)
"House came with great amenities and host was very communicative and flexible"
The price is $399
$793 total
includes taxes & fees
May 29 - May 30
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
1 bedroom, iron/ironing board, free WiFi, bed sheets
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
10.0 out of 10, Exceptional, (10)
"This property was perfect for a quick weekend getaway with my partner. The place was clean and inviting. There were a few snacks along with coffee and tea provided by the hosts. The bathroom was well stocked. The town itself is adorable with some good restaurants within close driving/walking distance and lots of outdoor activities. I definitely recommend staying here!"
Romantic sky loft with steam shower/giant tub. Minutes to the slopes.
Don't see what you're looking for?
See all available properties in 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.

Woodstock Vacation Rental Travel Info

Number of vacation rentals
38
Popular accommodation
Woodstock private vacation homes
Known landmarks
Mount Tremper Arts, James Cox Gallery and Overlook Mountain Trailhead
International airports
Hudson, NY (HCC-Columbia County) and Albany, NY (ALB-Albany Intl.)

Other types of properties in Woodstock you may be interested in

Superior Room, Fireplace, River View | Egyptian cotton sheets, premium bedding, down comforters, minibar
Woodstock Way Hotel
4.0 star property
9.6 out of 10, Exceptional, (89)
"An absolute pleasure. I wouldn’t stay over in Woodstock at any other lodging after finding this gem. "
The price is $300
$375 total
includes taxes & fees
May 30 - May 31
Woodstock Way Hotel
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (198)
"Spent two nights and wanted a place where we could easily bike into town and got exactly that! The sound of the creek outside was so relaxing, accommodations were clean and comfy. Definitely would return!"
The price is $169
$333 total
includes taxes & fees
Jun 3 - Jun 4
Streamside Cottage Walking Distance to Town of Woodstock
Exterior detail
The Herwood Inn
4.5 star property
9.8 out of 10, Exceptional, (33)
"Everything was great. Anything you want is there. Books, Records, Ice, Coffee ☕."
The price is $203
$228 total
includes taxes & fees
Jun 6 - Jun 7
The Herwood Inn
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 Woodstock 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 Woodstock 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 Woodstock vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. 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 Woodstock 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 $104 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 Woodstock rentals

At Expedia, we put the best Woodstock 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 Woodstock 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 Woodstock 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 Woodstock. 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 Woodstock?

Yes, there are vacation rentals in Woodstock close to Woodstock Music Shop, or you can choose a secluded option if you're looking for a relaxing stay. The forests and art scene are just a few reasons why tourists like Woodstock. Make sure you have time to check out the riverfront and mountain views during your trip.

What's the top vacation rental in Woodstock?

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace: This highly rated vacation home rental in Woodstock is located in the mountains 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 books.

How many vacation rentals are there in Woodstock?

Expedia has 69 vacation rentals for your stay in Woodstock.

What can I see and do in Woodstock?

Overlook Mountain Trailhead and Thorn Preserve - Catskill Center are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Woodstock Music Shop. Other places in town to visit include Woodstock Public Library and Woodstock Golf Club.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned properties you can reserve for several days or longer in Woodstock. Vacation rentals feature extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family gatherings.

Recent reviews of Woodstock properties
Expedia verified reviews

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

5/5 Excellent
The New Paltz Hampton Inn is wonderful!
"The New Paltz Hampton Inn is wonderful! Quiet, roomy, lots of food options, coffee all day"
A verified traveler stayed at Hampton Inn by Hilton New Paltz
Posted 17 hours ago
Hampton Inn by Hilton New Paltz