Holiday rentals with a pool in West Point

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in West Point

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

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Guest favourite

Home in Stormville

4.94 out of 5 average rating, 156 reviews

Private Hudson Valley Country Retreat

Beautiful 1930s house set on 18 private acres of land overlooking a private lake. Immaculately landscaped surrounding area with koi and gold fish pond with a waterfall, gazebo, hammock and most importantly untouched nature. Very private! Enjoy your morning coffee or tea in the outdoor covered patio overlooking the property, wine and dine under the pergola, enjoy the fire pit or wood burning fireplace on a chilly evening. Serenity and relaxation at its best! Pond dock coming up in Spring of 2021

20–27 Oct

$1,449 NZD per night

Guest favourite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

25 Oct – 1 Nov

$979 NZD per night

Guest favourite

Home in New Paltz

4.98 out of 5 average rating, 436 reviews

midcentury modern in ground pool walk 2 trail/town

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail Water St. mkt & the ❤️ of New Paltz Village. Several outdoor seating areas. The whole place is yours FULL PRIVATE ACCESS TO HOUSE/PROPERTY POOL OPEN MAY 1 - end of SEPTEMBER

6–13 Sep

$1,667 NZD per night

Guest favourite

Home in Stamford

4.97 out of 5 average rating, 220 reviews

Midcentury Modern ZenHouse Sculptor Studio

Zenhouse mission to inspire creativity, art, spirituality and rejuvenate.Experience complete tranquility in the Zen-like environment .Please read house rules before booking . Zen House Satori consists of an architecturally significant mid-century modern 3.5 acre private estate -main house @ Zenhouse in CT. This is the ideal setting for a memorable romantic getaway, solo adventures and business travelers – not to mention photoshoots and film locations! Inside Sculptor studio

24–31 Dec

$780 NZD per night

Guest favourite

Condo in Vernon Township

4.9 out of 5 average rating, 301 reviews

Appalachian TOP 4TH FLOOR Studio+ w/amazing views!

Location, location, location! This is a very unique, open concept unit. In lieu of a balcony, it has a huge picture window that allows breathtaking center building panoramic views of the slopes! It's also a top floor unit so extra height ceilings. That open concept continues inside where the walls were minimized leading to the master bedroom having an archway in lieu of a door. The result is a very spacious main living area perfect to gather in front of the fire.

12–19 Dec

$311 NZD per night

Guest favourite

Apartment in Suffern

4.95 out of 5 average rating, 105 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

11–18 Jul

$296 NZD per night

Guest favourite

Home in Pound Ridge

5.0 out of 5 average rating, 126 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Enter a freshly updated and thoughtfully furnished peaceful home surrounded by 14 acres of ancient trees, stone walls, and open meadows, in the town of Pound Ridge, NY. This natural light-filled guesthouse features all the elements needed to relax and unwind. In the summer months, guests have access to a heated saltwater pool, bask in the sun under a majestic maple tree, and enjoy the outdoor fire pit while stargazing at night.

7–14 Sep

$1,246 NZD per night

Guest favourite

Condo in Vernon Township

4.95 out of 5 average rating, 238 reviews

NYC Escape 1 hr away

Escape the concrete jungle and enjoy this modern rustic hideaway with breathtaking mountain views! Walk to Mountain Creek Water Park, go mountain biking, ziplining, alpine coaster, hiking, wine tasting and so much more! This newly remodeled 1-bedroom, 1-bath vacation rental has room for 4 and bright living area. Enjoy the outdoor pool, sauna, hot tub or make s’mores and gather around the fire pit and savor R&R time

13–18 Aug

$376 NZD per night

Guest favourite

Loft in Cornwall

4.86 out of 5 average rating, 394 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside in our private, cozy loft studio! Located on 1.5 acres, this clean and comfortable apartment includes a kitchenette with bar-style table, living room and flat screen Roku TV with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have their own parking space, a private first-floor entrance, full bathroom, patio, BBQ and fire pit!

6–13 Mar

$172 NZD per night

Guest favourite

Guest suite in Holmes

4.98 out of 5 average rating, 165 reviews

Pool opens 5/24! Huge & Eclectic 1.5 hr to NYC!

1.5 hrs from NYC; minutes driving from hiking trails; 20 min from Beacon and Cold Spring! The bottom floor of this 1865 Carriage House has been transformed into an eclectic retreat. The 2500 sq ft private apartment has a room for every mood and super unique decor in every corner! There is also a vintage/antique shop on the property— 20% off for our guests ;)

19–26 Nov

$399 NZD per night

Guest favourite

Guesthouse in Brewster

5.0 out of 5 average rating, 290 reviews

The Cottage by the Lake: Hudson Valley Indulgence

The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

1–8 Aug

$412 NZD per night

Guest favourite

Guest suite in New Paltz

4.95 out of 5 average rating, 327 reviews

Majestic Studio with Shawangunk Mountain Views

Are you looking for a perfect romantic getaway? Whether you are active and are looking for a place to hike or want to take a lover's tour through the guided Hudson Valley wineries, our newly renovated private studio awaits you in lovely New Paltz. We do not allow any pets.

5–12 Aug

$327 NZD per night