Holiday rentals with a pool in Woodbury

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Woodbury

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

%{current} / %{total}1 / 1
Top guest favourite
Home in Newburgh
4.98 out of 5 average rating, 131 reviews

Fable Retreats: Hudson River House

Friends and family will be wowed when gathering at this spacious mid-century riverfront home. There’s a beautiful new gunite pool, hot tub, large patio, screened floating porch, and spacious decks for barbecuing and dining. Interiors feature 2 fireplaces, 2 living spaces with large TVs, fully-equipped kitchen, game room, exercise area, piano, home office, and lots of space to spread out both inside and outside. All of it looks out to the Hudson River where you may spy bald eagles nesting nearby.

Top guest favourite
A light-filled living area features a comfortable sofa and a blue armchair, complemented by a modern coffee table. Two framed images hang on the wall, with a large window providing views of the greenery outside.
Flat in Vernon Township
4.95 out of 5 average rating, 107 reviews

Mountain Creek Appalachian Apartment Ski slope

Relax in the most convenient Condo in Appalachian Hotel with the whole family at this one bedroom apartment, peaceful place to stay. All amenities Resort just at walking distance to Mountain Creek Ski Slope!!, 1st Floor one bedroom apartment just in front of the pool , jacuzzi and sauna facilities! Open the curtain to enjoy the Mountain Creek and natural resources views!, let us pamper you with robe and slippers available for your comfy outdoor heated pool, hot tub and sauna open all year round

Guest favourite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Mountainville
4.84 out of 5 average rating, 615 reviews

Country Getaway - Close to Hiking & Storm King

Enjoy the countryside minutes away from downtown restaurants, bars and Main Street, 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 two flat screen Roku TV’s with Netflix, Hulu as well as an electric fireplace, outdoor patio and fire pit. Guests have two parking spaces, a private first-floor entrance, private full bathroom, outdoor dining area, BBQ and fire pit! Pool available seasonably.

Top guest favourite
Cabin in Tobyhanna
5 out of 5 average rating, 113 reviews

Romantic Log Cabin W/ Hot Tub, Fire Pit, Projector

Immerse yourselves in the perfect blend of serenity and romance at our fully renovated Poconos log cabin. It offers a private feel, while located in a safe neighborhood. Cuddle up in our living room day bed while enjoying backyard forest views through the giant picture window. Relax in the hot tub or by the fire pit where memories are made! Centrally located, the cabin provides access to ski resorts and hiking trails. As guests, you'll also enjoy access to the lake, pool, and sports courts.

Guest favourite
A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.
Home in Woodstock
4.97 out of 5 average rating, 168 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..

Top guest favourite
A spacious living area features large windows allowing natural light to fill the room. A stone fireplace is prominently placed against a wooden wall. Comfortable seating arrangements include a large sectional sofa, with decorative plants adding a touch of greenery.
Home in Yorktown Heights
4.91 out of 5 average rating, 175 reviews

Cozy getaway 1 hr from NYC!

This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Top guest favourite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring
4.95 out of 5 average rating, 177 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, 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.

Top guest favourite
A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.
Flat in Chester
4.98 out of 5 average rating, 145 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Guest favourite
A modern kitchenette is displayed, featuring white cabinetry and stainless-steel appliances. A comfortable brown sofa is positioned near a wooden coffee table. A dining area with a white table and chairs is also visible, alongside large windows allowing natural light into the space.
Flat in Suffern
4.92 out of 5 average rating, 152 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.

Superhost
A well-equipped kitchen features wooden shelves with dishes and a coffee maker. A modern sink and black faucet are complemented by a smooth countertop, while natural light filters through a window adorned with greenery. Kitchen essentials are organized for convenience.
Flat in Brookfield
4.91 out of 5 average rating, 303 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley
4.95 out of 5 average rating, 111 reviews

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Escape to a stylish 3BR cottage with a private pool, cinema room, game room, and fire pit - perfect for families, couples, or solo travelers. Surrounded by woods and just minutes from Cold Spring, hiking trails, ski resorts, and charming shops. Relax by the electric fireplace, enjoy movie nights, play pool, or unwind with forest views from your private deck. A cozy, well-equipped retreat for peaceful getaways and Hudson Valley adventures year-round.

Guest favourite
The image captures a lively game room featuring a slide, colorful play structures, and a cozy seating area. A spacious dining area is visible, with large windows overlooking the scenic mountain view. The wooden accents and modern decor create a welcoming ambiance.
Townhouse in Tannersville
4.99 out of 5 average rating, 233 reviews

Mountain Top! Family Paradise w Hot Tub & Game Rm

Best Poconos MOUNTAIN TOP vista! We're not simply offering a house with a stunning MOUNTAIN view, a newly completed gut renovation, contemporary furniture, stylish decor, an airy atmosphere, along with a remodeled game room and private hot tub; we’re providing an elevated mountain top living experience-an unforgettable journey you'll treasure for a lifetime. Take a look at all the details. Book now and experience the ultimate in mountain living!

Popular amenities for Woodbury rentals with a pool

Quick stats about holiday rentals with a pool in Woodbury

  • Total holiday rentals

    Explore 20 holiday rentals in Woodbury

  • Nightly prices starting at

    Woodbury holiday rentals start at € 60 per night before taxes and fees

  • Verified guest reviews

    Over 430 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Woodbury holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodbury rentals

  • 4.9 Average rating

    Woodbury stays are highly rated by guests – averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. New York
  4. Orange County
  5. Woodbury
  6. Rentals with pools