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

22–29 Oct

€ 809 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.

22–29 Oct

€ 547 per night

Guest favourite

Apartment in Vernon Township

4.97 out of 5 average rating, 216 reviews

Rustic Chic at Mountain Creek! Pool|Hot Tub|Sauna

From skiing, snowboarding to mountain biking, waterpark, hiking, zip lines, open year round heated pool, hot tub, sauna & more! Enjoy all that Rustic Chic at Mountain Creek has to offer! 1B/1b condo w/king bed, queen sofa bed & cozy fireplace -The perfect getaway for a couple, small group or family! Steps to Mountain Creek Ski Resort & Waterpark.* *Located in The Appalachian directly next to Mountain Creek Resort! "Comfortable, chic, super clean, and thoughtfully decorated condo."~Marianne

1–8 Dec

€ 165 per night

Guest favourite

Flat in Kent

4.93 out of 5 average rating, 127 reviews

Loft 22

Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*

3–10 Feb

€ 159 per night

Guest favourite

Home in New Paltz

4.98 out of 5 average rating, 437 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

14–21 Jul

€ 915 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

10–17 Nov

€ 435 per night

Guest favourite

Flat in Suffern

4.95 out of 5 average rating, 106 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.

7–14 Jun

€ 166 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.

14–21 Dec

€ 701 per night

Guest favourite

Apartment 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

€ 206 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!

11–18 Jan

€ 96 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 ;)

24–31 Aug

€ 233 per night

Guest favourite

Guest house 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

€ 231 per night