Find Vacation Rentals in Woodstock

Highlights Woodstock

  • Countryside rentals
  • Destination in New York
  • Family getaway
  • Outdoor adventures
  • Historical landmark
  • Hiking trails

Best Vacation Rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.
Woodstock, Catskill Mountains
Vacation Rental • 797 ft² • 2 Bedrooms
(7 reviews)
Escape to your private, treetop hideout right in the village of Woodstock. Peaceful & private, this upper unit has an easy, open floor plan with beautiful wide board pine flooring throughout. The new kitchen is complete with breakfast bar. A sizable living room leads out to the balcony surrounded by treetops, perfect for relaxing and down the steps is your private backyard with BBQ. Two beautiful bedrooms provides more woodsy views and enhances the serene vibes of this home. Take advantage of all that Woodstock has to offer. Just steps to best restaurants, galleries, pubs, yoga, theatre...
from $206 / night
Woodstock, Catskill Mountains
Vacation Rental • 4 Guests • 2 Bedrooms
(10 reviews)
Woodstock Village- country cottage offers in town connivence with private fenced yard, surrounded by woods. Walk to everything.( NYC BUS) The cottage has an upstairs which is 1 large bedroom with a king bed. The downstairs bedroom has a daybed ( 2 twins). The living room has 2 couches, dining table, cable TV, screened french doors that opens to the woods and dutch front door opens to the patio. Full kitchen,microwave, cooking basics ( spices, teas, coffee, condiments, dishes,pots, & pans ) Newly renovated bath with travine tile & marble. Outdoor patio with propane BBQ, and dining/ s...
from $154 / night
Woodstock, Catskill Mountains
Vacation Rental • 1195 ft² • 2 Bedrooms
(47 reviews)
WALK TO EVERYTHING IN THE VILLAGE FROM THIS NEWLY RENOVATED COTTAGE WITH GORGEOUS VIEWS! Located in the center of the village, this renovated cottage is open, cozy, and perfect for a Woodstock vacation or weekend getaway. Convenience is the name of the game here. No vehicle is necessary. It is a short walk to the Trailways bus stop, restaurants, shops, art galleries, and hiking. This rental is blessed with beautiful views of the Sawkill Creek and Tannery Brook.The fully equipped kitchen has all new stainless steel appliances, granite countertops, dishwasher, microwave, toaster and coffee ma...
from $405 / night

Prices and availability

Current Vacation rental prices Woodstock

$317for 25 Mar - 1 Apr
$241 annual average
Average price per week

Current vacation rental availability Woodstock

31%for 25 Mar - 1 Apr
38% annual average
Percentage of available rentals

Vacation rentals in Woodstock

Amazing rental locations in Woodstock

Plan your next trip to the beautiful town of Woodstock. You will find this town located in the Ulster County of the state of New York, United States of America. Situated in the northern part of the county, bordering the city of Kingston, this town has a population of 5,884 inhabitants, ideal if you want to find a peaceful place in the countryside. The area also holds a rich and extensive history, the first non-indigenous settler arrived around 1770 and Woodstock was established in 1787.

Vacation Rentals in Woodstock

There are numerous rental properties you will be able to enjoy while visiting Woodstock. Imagine spending your morning having a healthy breakfast on the patio and feeling the fresh breeze of the countryside. Spend the afternoon swimming in your private pool during a warm day. Enjoy an evening cozy by the fireplace with your family during a cold winter night. These are some of the memories you could be making in Woodstock.

Vacations in Woodstock

The area and getting around

You will find numerous ways to make your trip to Woodstock. If you want to make your way to Woodstock by train, the closest train station is the Poughkeepsie Amtrak Station which is connected to the town by bus. If you want to make your journey by plane, the closest airports to Woodstock are Lebanon Airport, Rutland Airport, and Burlington Airport.

Where to eat in Woodstock

Although Woodstock is a small town, you will be able to find many great eateries to enjoy during your stay. If you are looking for an upscale dining experience, head over to Silvia. This local favorite restaurant serves a menu that can delight vegetarians, vegans and omnivores alike. The dishes are globally-inspired and feature a variety of meat-free options from local, seasonal and sustainable sources. On the other hand, if you want something more casual, check out Dixon Road Side. Here you will be offered a menu filled with barbecue items such as their famous BBQ beef brisket plate.

Travelers and activities

Woodstock for outdoor explorers

There are many outdoor activities to enjoy during your stay in Woodstock. If you want to go for a hike, head to the Olde Rope Mill Park. Here you will find nature trails that take you across the local flora and fauna of the town. On the other hand, if you want to go on a bike ride, check out the Little River Trail. This short trail will take you alongside the river and the bike path is perfect for riders of any level.

Woodstock for family activities

If you are planning to take your family on vacation to Woodstock, try out one of these activities altogether. For a fun and creative activity to do on a cold afternoon, go to the Artistree Community Arts Center. This non-profit establishment offers art inspired workshops for the kids, as well as seasonal classes. Another great educational experience to have in Woodstock is visiting the Billings Farm and Museum. This spot opened in 1968 and since then it offers a look into the historic Billings Farm and the heritage of a rural farm.

Did you know that the Sound-Outs concert which was held in Woodstock inspired the original Woodstock Festival?

Top 5 travel tips for Woodstock

1. Catskill Park

Explore the natural landscape. Established in 1885 these 286,000 acres of land has been preserved and protected from development. Here you will be able to find over 35 ridges to hike.

2.Ashokan Reservoir

Go for a bike ride. The reservoir is one of the largest in the United States of America and it has more than two miles of pristine views to enjoy during a bike ride. These trails are stunning as you will be able to see the mountains all around.

3. Woodstock Artists Association and Museum

If you want to experience some local art, this is the place for you. The local artist started to become famous from the Byrdcliffe colony which was founded in 1903. Now at this museum, you will be able to learn the history of artistry in Woodstock while admiring the art itself.

4.Tinker Street

Take a walk through one of the most unique streets in the nation. In this area, you will be able to find art galleries, boutiques, restaurants and the Woodstock Reformed Church, which was built in the mid-19th century.

5.Outdoor Markets

Support the local business while in Woodstock. Check out the Mower's Saturday/Sunday Flea Market which is located near to the Vil lage Green (on Maple Lane). Here you will find vintage clothes, jewelry, fresh farm produce, wood-fired pizza, and more.

FAQs: Vacation Rentals in Woodstock

How much do the vacation rentals in Woodstock cost on average?

At an average cost of $264 per night, Woodstock lies at the lower end of the price range for vacation rentals in the USA.

During which months can you find the best price for vacation rentals in Woodstock?

If you would like to save the maximum during your visit to Woodstock, go there in August ($222 per night on average), May ($245), or April ($248), to find the lowest prices for the whole year.

When are vacation rentals more expensive in Woodstock?

Last year, the month that showed the highest annual average prices in Woodstock was November, with an average price of $292 per night. This was followed by September, with an average of $288, and then October, with $278.

Is Woodstock a good location for a last-minute getaway?

In order to not have problems finding accommodation in Woodstock, it is necessary to be proactive as 90% of rentals are usually booked, according to the data from last year.

When are more vacation rentals available?

Last year, the months with the largest number of properties available of the year in Woodstock were January, December and September, with average availabilities of 23%, 22%, and 16%, respectively.

How many rentals are there in Woodstock?

Holidu offers around 120 accommodations in Woodstock from 2 different providers, so find the perfect type of accommodation you are looking for. You can count on us!

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