Vacation rentals with a pool in Town of Crawford

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Top-rated rentals with a pool in Town of Crawford

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

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Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 510 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 favorite
A cozy bedroom featuring a spacious bed with white bedding and decorative pillows. Two bedside tables with lamps flank the bed, providing soft lighting. A textured wooden accent wall adds warmth to the space, complementing the neutral tones of the room.
Condo in Vernon Township
4.98 out of 5 average rating, 311 reviews

Ski-in/Ski-out, Hike, Bike, Wine-Rustic Chic Stays

Ski-In/Ski-Out, Waterpark & Biking - Just Steps Away! Ski, snowboard, bike, hike, zip line-or relax in the Appalachian's outdoor, year-round, heated outdoor pool, hot tubs, & sauna. This 1 bedroom, 1 bath condo has a King bed & Queen sofa bed-perfect for a couple, small group or family getaway. Located in The Appalachian, right next to Mountain Creek Resort! In the heart of Vernon Valley-near farms, golf, the Appalachian Trail & Warwick, NY. Plus, just 30 minutes to LEGOLAND & 1 hour from NYC!!

Top guest favorite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook
4.96 out of 5 average rating, 373 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite
Apartment in Wappingers Falls
5 out of 5 average rating, 229 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

Top guest favorite
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, 393 reviews

Kapitan’s Cottage Private Upstate Catskill Retreat

A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities, parks & Ski slopes.

Top guest favorite
An aerial view showcases a modern home surrounded by lush greenery. A curved path leads to the back, where a heated pool is visible, accompanied by outdoor seating and a pergola among the trees. The serene landscape offers a sense of seclusion.
Home in Pine Bush
4.99 out of 5 average rating, 104 reviews

Hudson Valley Oasis - Sauna, Hot Tub, Heated Pool!

A modern oasis in the Hudson Valley near hiking, skiing, apple-picking, antiquing, and other fun seasonal activities only 1.5 hours from NYC. Enjoy swimming in a heated pool? Great! We have a beautiful pool (Opens 4/1) and pool house complete with an outdoor bar and hot tub. Lovely outdoor garden with a fire pit nestled in the middle. A patio with a gas grill and pizza oven is ready for all chefs. We feature a three-person sauna inside! Just secluded enough to be perfect for larger gatherings!

Top guest favorite
A heated pool is surrounded by a stone deck, featuring several black lounge chairs positioned under black umbrellas. Lush greenery is visible in the background, providing a serene, natural setting.
Home in Putnam Valley
4.99 out of 5 average rating, 156 reviews

*Large Pool* Garrison Ultra Modern 5B hottub sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

Guest favorite
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, 599 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 favorite
The collage showcases different areas of the home and yard. An outdoor seating area with a pergola and hot tub invites relaxation, while a spacious pool lies in the background. The living area features a cozy setup with a Peloton bicycle, and the kitchen area includes a bar, enhancing social gatherings.
Cottage in Kerhonkson
4.81 out of 5 average rating, 198 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

This charming 2-bedroom cottage is nestled on an acre of private, untouched wilderness, making it a great place for nature lovers, hikers, and couples looking for the perfect getaway. When you’re not exploring Minnewaska State Park, enjoy the pool, stargazing from next to the fire pit, and soaking tired muscles in the hot tub. 6 Min Drive to Minnewaska State Park Preserve 10 Min Drive to Stony Kill Falls 15 Min Drive to Wightman Fruit Farm Experience Kerhonkson With Us & Learn More Below!

Superhost
Cabin in Kerhonkson
4.82 out of 5 average rating, 258 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 favorite
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, 154 reviews

Le Petit Abris 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.

Top guest favorite
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, 141 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.

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