Vacation rentals with a pool in Putnam County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Putnam County

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Beacon

4.93 out of 5 average rating, 85 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

Welcome to Hudson Valley Hideaway, a stylish family friendly home tucked away in the corner of Beacon, off the shores of the Hudson. 4 Bedrooms, 2 bath, pool+hot tub home, stocked kitchen, dining room, chic living room w/ 85"TV, 1 King, 2 Queens, 1 Twin XL, with fast internet (1gb), dedicated workspace & A/C. Amenities galore, outdoor space w/grill, firepit and fenced pool w/ slide & diving board. Experience a little slice of Beacon in this cozy home with modern city comforts,1.5 miles from DT

Feb 9 – 16

G$91,261 GYD per night

Guest favorite

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.

Oct 26 – Nov 2

G$115,420 GYD per night

Guest favorite

Cottage in Putnam Valley

4.98 out of 5 average rating, 46 reviews

Beautiful Cottage in Hudson Valley w/Pool & Views

Welcome to our beautifully renovated and thoughtfully decorated cottage in the charming town of Putnam Valley! Tucked away in a quiet, wooded setting, this cozy retreat is the perfect getaway for couples, families, solo travelers. Enjoy breathtaking sunsets over the Hudson Valley from your private deck, surrounded by lush trees and wildlife. Located just a short drive from the bustling town of Cold Spring, the cottage is perfectly situated for exploring all that the Hudson Valley has to offer.

Sep 2 – 9

G$104,416 GYD per night

Guest favorite

Apartment in Cortlandt

4.89 out of 5 average rating, 19 reviews

The Lake House

Allow the mountain views, abundance of trees, the sound of the stream below and chirping birds to greet you at this crisp and clean lower level apartment with its own entrance. Take in the atmosphere of the quiet lake community nestled away in the woods away from the rest of Westchester. Take a dip in the heated pool, huddle around the fire pit, use Hulu w/ live television, enjoy central air. The couch in the living room pulls out to a queen sized bed. Please note, a cat and dog live upstairs.

Oct 23 – 30

G$40,495 GYD per night

Guest favorite

Apartment in Hopewell Junction

4.92 out of 5 average rating, 75 reviews

3BR Retreat w/Pool/Firepit near Appalachian Trail

ValleyView is THE ULTIMATE FAMILY GETAWAY nestled up against the Appalachian Trail surrounded by a forest preserve. We are less than an hour from Manhattan. Explore the historic hamlet of Hortontown...or just stick by your pool! You are: a 3 minute walk to the Appalachian Trail 5 minutes from Fishkill Farms 8 minutes from Fahnestock State Park 14 minutes to the Empire State Rail Trail 15 minutes to Beacon or Hudson Highlands State Park 27 minutes to Walkway Over The Hudson!

Apr 18 – 25

G$47,378 GYD per night

Guest favorite

Home in Carmel Hamlet

4.92 out of 5 average rating, 66 reviews

Country getaway with pool and spa on 9 acres

Escape the city, located just over an hour from Manhattan & 7min from Metro North, to work or play. Open floor plan is great for entertaining and relaxing. Enjoy the large wood burning fireplace, 7 person hot tub, lots of windows, work spaces with monitor, private HVAC in each bedroom, and tons of private outdoor space, full amenities and everything you need included. Pool is closed for the season but will open around memorial day. Hot tub is OPEN year round.

Aug 15 – 22

G$138,881 GYD per night

Guest favorite

Home in Philipstown

5.0 out of 5 average rating, 13 reviews

Modern Cottage in the Woods, Garrison

Relax with the whole family at this peaceful natural retreat. This modern rustic home is set on 4 private acres of serene natural habitat, adjacent to hiking trails and a stream on wooded public lands. Entertain by the outdoor firepit. Have a BBQ using the Weber smoker grill. Listen to the birds with a morning coffee on the upstairs terrace. Relax by the modern fireplace or in the TV lounge. Close to West Point and Cold Spring. Pool is closed for the season.

May 6 – 13

G$92,505 GYD per night

Guest favorite

Home in Mahopac

5.0 out of 5 average rating, 15 reviews

Heated Pool | Hot Tub | Fire Pit | Backyard Oasis

Welcome to our charming house located in the picturesque town of Mahopac, NY. This stunning property is perfect for families or small groups of friends looking for a peaceful and relaxing getaway. Our house boasts three spacious bedrooms with comfortable beds, three modern bathrooms, and gorgeous vaulted ceilings throughout. You'll love the bright and airy feel of the house as well as the tasteful decor and comfortable furnishings.

Jul 11 – 18

G$178,310 GYD per night

Guest favorite

Vacation home in Holmes

5.0 out of 5 average rating, 16 reviews

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Dec 25 – Jan 1

G$114,397 GYD per night

Guest favorite

Home in Mahopac

5.0 out of 5 average rating, 14 reviews

Farmhouse with Pool Hudson Valley 1 hr from NYC

Beautifully designed Hudson Valley farmhouse only 1 hour from Manhattan. Close to all the great Hudson Valley towns including Beacon, Cold Spring, Katonah, Bedford Hills, Peekskill, Pleasantville, Croton Falls and North Salem. Fifteen minutes to several lakes, great hiking trails, farm stores, breweries, orchards, and pick-your-own farms. Come get cozy by the fire and enjoy everything the Hudson Valley has to offer!

Aug 28 – Sep 4

G$130,570 GYD per night

Guest favorite

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 ;)

Nov 20 – 27

G$45,234 GYD per night

Guest favorite

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.

Aug 1 – 8

G$48,892 GYD per night