Vacation rentals with a pool in Woodstock

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Top-rated rentals with a pool in Woodstock

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 192 reviews

Glenford Studio with Pool & Mountain Views

Come escape to the country & experience peace & serenity. Our large studio is a vacation gem and home away from home on 10 mtn top acres with large shared pool. High-speed wifi Work remotely. The studio is on a private road just 5 mins from the center of Woodstock. Perfect for a couple, small family or single. 30 day rentals preferred. Please contact us to inquire. Halloween in Woodstock is Magical! Come join the town Halloween parade & festivities. Booking Thanksgiving. Xmas, New Years

Jul. 15 – 22

$522 CAD per night

Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 154 reviews

Woodstock Home Close to 3 Towns, Hiking and More

If you're looking for the perfect mix of privacy and easy access to Woodstock, Kingston, Saugerties and things to do, this rental may be ideal for you. There is plenty of room to relax, cook your own meals or work in a peaceful setting, and we're close to hiking trails, theaters and over 30 restaurants. (see regional guidebook under info for guests). The entire 1,200 square foot home is made available to you, but please note that guest access is limited to 2 people (see polices and rules).

May 8 – 15

$286 CAD per night

Guest favourite

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. Building also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

Oct. 31 – Nov. 7

$1,032 CAD per night

Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 209 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Pool is open! Secluded country estate, a short drive to Woodstock, this Japanese teahouse is the ideal combination of away-from-it-all and convenience. The backyard is designed to make the most of the outdoors. Whether you’re here when the trees are turning golden brown in autumn, or when the sun shines in summer, there’s a spot outside for you. Sunny months see barbecues by the fire pit beneath, the stringed lights and swimm in the salt pool, play a game of tennis or bball and chill.

Dec. 29 – Jan. 5

$371 CAD per night

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 100 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Jan. 15 – 22

$1,202 CAD per night

Guest favourite

Home in Woodstock

4.85 out of 5 average rating, 191 reviews

Heated Pool/Private: Woodstock Mediterranean

Say hello to your perfect vacation home! Bright and airy Woodstock home with all the amenities you will need. Located only 4 minutes from the Village of Woodstock. Four-bedroom house with 3 full bathrooms located on private roadway perfect for walking & running around neighborhood. The house features heated salt-water in ground pool, 2000sf outdoor deck with BBQ grill, fire pit, basketball court, and large tranquil garden with privacy, two wood burning fireplaces, and central air.

Aug. 12 – 19

$1,340 CAD per night

Guest favourite

Home in Woodstock

4.84 out of 5 average rating, 115 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! Please check for pool opening/closing. In addition to the main house there is also a studio cottage (with bathroom) that can be used as a WFH private office. It has it's own high speed internet.

Nov. 27 – Dec. 4

$818 CAD per night

Guest favourite

Home in Woodstock

4.89 out of 5 average rating, 159 reviews

Secluded 7acres, Saline Heated Pool, Spa, Stream !

Our pool is now closed until mid-May. (NOTE: Unlike other Hosts, we do not charge extra for heating our pool!) FREE FIREWOOD the fireplace! Relax on 7 acres of total privacy! Pamper yourself in the heated pool + hot tub. Sip your coffee by the stream, snooze in the hammock; stroll in the woods or hop to town in 5 minutes for shopping, dining & fun! (GREAT for kids: we have ping-pong, a basketball net, a vintage doll house with furniture!).

Sep. 15 – 22

$987 CAD per night

Guest favourite

Cabin in Saugerties

4.99 out of 5 average rating, 123 reviews

Lovely cabin by the stream

We are close to HITS, Hunter Mtn and all of the wonderful activities of the Hudson Valley. This is a very peaceful cabin, steps from the stream. We are perfect for single guests or a maximum of two people (including children) as the cabin is quite small. The cabin is private and set in the woods, yet steps away from the pool, sauna, screen house. We are a carbon neutral property, with a large solar array and a Level 2 EV charger.

Oct. 18 – 25

$231 CAD per night

Guest favourite

Guesthouse in Kingston

4.92 out of 5 average rating, 288 reviews

The Antique Stone House

A Private Guesthouse in the historic Antique Stone House built in 1810 is awaiting your visit. This Stone House offers a great location in the beautiful Historic City of Kingston, New York, (First Capital of New York State. ) located 90 miles north of Manhattan, for trips, adventures, and outings in every direction. Close to Stockade District and the Waterfront.

Sep. 28 – Oct. 5

$281 CAD per night

Superhost

Home in woodstock

4.86 out of 5 average rating, 486 reviews

CABIN WITH HOT TUB OUTDOOR FIREPLACE PIZZA OVEN

Perfect get away cottage for a couple or small family! 40 minutes to Hunter or Belleayre Newly renovated home on 6 acres with bright rooms and forest views; outdoor patio with hot tub Jacuzzi; outdoor fireplace and pizza oven; new whole-house water filter. The cabin is 10 minutes to the town of Woodstock. It is directly across from Kenneth Wilson State Park

Aug. 15 – 22

$418 CAD per night

Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 305 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Sep. 21 – 28

$695 CAD per night