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Holiday rentals with a pool in Crawford

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Crawford

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

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Top Guest favourite
Home in New Paltz
4.98 out of 5 average rating, 521 reviews

midcentury mod * HOT TUB * walk out trail 2 mohonk

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. fireplace, 5 person hot tub short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village THE WHOLE PLACE IS YOURS- HOUSE, PROPERTY, POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

Top Guest favourite
Apartment in Wappingers Falls
5 out of 5 average rating, 234 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

PLEASE READ ALL HOUSE RULES PRIOR TO INQUIRIES AND BOOKINGS! 1 night/longer stays can be accommodated upon request and calendar availability. “Home Is Where The Heart Is”. If you love tranquility and coziness combined with sophistication and traditional rural charm, this is the place for your stay (only 4 miles from Beacon). The ground floor apartment with a private entrance (located around the back in a private house) includes a living room, full kitchen, full bathroom and Queen bedroom

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
4.85 out of 5 average rating, 625 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.

Guest favourite
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.87 out of 5 average rating, 196 reviews

Scenic River View Escape | New Paltz

Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

Superhost
Cabin in Kerhonkson
4.81 out of 5 average rating, 263 reviews

Woodland Hideaway: Sauna, Tennis Court & 15 Acres

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features heated pool, sauna, large 2000sf deck overlooking forest, full size tennis court, 15.5 acres for hiking, fishing, and exploring. Located only 2 hours from New York City & 20 mins from Woodstock. Two-bdrm house with one full bathroom and loft sleeping space. House is located on a quiet road. Turn into the private driveway and get ready to relax and mingle with Mother Nature

Top Guest favourite
A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.
Cabin in New Paltz
4.95 out of 5 average rating, 157 reviews

The Little Shelter at Gunks EcoLodge

Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

Guest favourite
A spacious bedroom features a large king bed adorned with a patterned quilt and decorative pillows. Soft lighting from a bedside lamp illuminates the area, while the en-suite bathroom is visible through an open door. Neutral tones and artwork add a touch of elegance.
Condo in Vernon Township
4.8 out of 5 average rating, 302 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

The Appalachian is a true 4 season resort overlooking Mountain Creek Ski Resort/ Waterpark and other activities such as farms, mountain biking, multiple golf courses, horseback riding, and ziplining! NEAR LEGOLAND (25 min drive) Hike the Appalachian Trails, tour the wineries and enjoy Octoberfest/Spas/Pumpkin and Apple picking. This is a true 4 season resort with a heated(in winter) year-round OUTDOOR pool/hot tubs/Suana. Ski-in/out right to the main lift from the building

Top Guest favourite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 403 reviews

Kapitan’s Cottage Private Winter Retreat Kingston

Escape the city to this cozy vintage rustic Catskills retreat—perfect for couples, families, and pet-friendly winter getaways. This 2BR, 1.5BA two-story home blends country charm with modern comforts, a large private yard, stone deck, fire pit, and BBQ. Close to skiing, hiking, parks, Kingston, Woodstock, and High Falls—yet secluded enough to truly unwind. Ideal for weekend or midweek escapes upstate. Pet-friendly, generator on-site. Inground salt pool open Mid May- Sept.

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.
Apartment in Chester
4.98 out of 5 average rating, 146 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.

Top Guest favourite
Guest suite in Hyde Park
4.98 out of 5 average rating, 242 reviews

The Harvest Guest House~ Hidden Gem with Pool

Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.

Top Guest favourite
The living area features a comfortable couch and armchair, with large windows providing natural light and views of the outdoors. A wooden dining table with four chairs is positioned near the windows, while a coffee table sits in front of the couch. Shelves hold various books and decorative items.
Guest suite in New Paltz
4.95 out of 5 average rating, 424 reviews

Airy & Private Escape on Mountain Rest Road *Pool*

Relax and unwind in our bright and private 2BR apartment located at the edge of Unison Arts Center’s sculpture garden (paths through woods and fields). A mile from New Paltz on the way to Mohonk Preserve, this simple but comfortable space features work by local artists and regional photographs. One of the bedrooms has an additional half-bathroom with a hand-made mosaic. Guests have their own entrance.

Superhost
A serene view of a tranquil lake is framed by tall trees at dusk. The water reflects the soft colors of the evening sky, while a grassy slope leads down to the shore. A small structure is visible to the left, enhancing the natural setting.
Cottage in Monticello
4.84 out of 5 average rating, 112 reviews

bungalow summer cottages on the lake Catskills

Catskill summer bungalow with 1950s flair 100 acre lake , tennis, full kitchen ,hiking ,all NY upstate has to offer for a weekend or all summer near casino and new water park near great country food and fairs and all the fishing and lazy days on the lake you can enjoy .Finish your night with music and spirits by the campfire plus spectacular 4th of July fireworks display

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