Holiday rentals with a pool in Delaware County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delaware County

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

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Superhost

Home in Livingston Manor

5 out of 5 average rating, 3 reviews

Livingston Manor Retreat

Only 2 hours from NYC, 5 minutes from the popular Catskills town, Livingston Manor, you’ll find this designer home and nature retreat. The home is filled with windows overlooking the wooded backyard, and a gurgling stream going off in the distance. Glass doors take you out to the sprawling patio that hosts a large dining table, solo stove, sun loungers and a plunge pool for the hot summer days. The house is designed as a calm retreat with daily luxuries and a social space for family and friends.

Top Guest favourite

Home in Downsville

4.98 out of 5 average rating, 133 reviews

Trout fishing on the Delaware

Beautiful Private area 2 homes on 10 acres, you will have one, newly built with all amenities, on the river, great fishing, luxurious accommodations, fire stove, local town full size pool with full access, pond / beach with boating, local Knack/ Canoe rental on the East branch of the Delaware River all within 20 minuets. Local antique shops, fairs and markets, Enjoy the Catskills Today. The property boarders the River Just a walk Away. Great for Family and Children. Local food, Shopping and fun

Superhost

Chalet in Gilboa

4.89 out of 5 average rating, 114 reviews

Modern Chalet w/Outdoor TV & Covered HOT TUB+POOL

Welcome to the beautiful Catskills! Our new beautiful A-Frame Chalet is situated on 6 acres of private forested land with lovely views of nature. Come stay in the fresh air! The chalet is fully stocked to be enjoyed for all seasons! Relax under the covered patio in all weather (rain or snow) in the HOT TUB or lounging on outdoor sectional while watching some NETFLIX/YOUTUBE TV all year round on our OUTDOOR TV, shoot a game of POOL in our upstairs Loft, or take a hike through our private TRAIL!!

Guest favourite

Dome in Hobart

4.93 out of 5 average rating, 159 reviews

Mtn View Lux Dome w/ Heated Plunge Pool

This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

Superhost

Home in Roscoe

4.75 out of 5 average rating, 102 reviews

Roscoe Haven

Situated on 1 acre of land, 2 hours from NYC, Roscoe Haven is a private oasis. 4 bedrooms & 3 bathrooms comfortably sleep up to 14 guests. Indoor game room features large screen TV, the fully stocked kitchen & dining room w/ indoor fireplace provide a cozy atmosphere. Backyard & deck overlook a flowing stream. Seasonal swimming pool, year-round hot tub, outdoor deck w/seating areas, BBQ, fire pit, play set & ample parking. Perfect for families, friends & couples seeking a peaceful getaway.

Guest favourite

Home in Roxbury

4.94 out of 5 average rating, 72 reviews

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View

Welcome to Canopy Hill House, a thoughtful and design focused home in Roxbury, NY. Our 3 bedroom, 2 bath property is perfect for a ski getaway or summer escape. You will find incredible details throughout and relax on our stunning deck with endless mountain views. Unwind in our 28 foot saltwater pool (June-Sept) and large deep cedar soaking tub (year-round) that fits 6 adults. Ski Mountains nearby: 15 min from Belleayre, 10 min from Plattekill, 30 min from Windham and 40 min from Hunter

Top Guest favourite

Cabin in Mount Upton

4.94 out of 5 average rating, 101 reviews

Log Cabin in the Country

Outdoor space with hot tub and un heated pool. All of all 3 upstairs bedrooms ( 1 queen bed, 1 with a bunk + 1 double bed, and 1 loft room with queen ), 2 full baths one with washer and dryer, kitchen & living room spaces. You are the only reservation in the home. Lots of hiking and quiet space, yet close to the village (10 min.) and the city of Oneonta (30 min.) or Cooperstown (45-60min). Play or rest.The hosts may be in residence however the owners presence is negotiable on request.

Superhost

Cabin in Walton

4.83 out of 5 average rating, 132 reviews

Catskills Cabin Off the Grid Experience

Escape the chaos of urban life and embark on a rustic retreat like no other! The property hosts the cabin and a tiny house (also for rent), nestled on a secluded pond. Offering a serene sanctuary that beckons you to unwind and reconnect with nature. Step inside to discover the cozy embrace of reclaimed barn wood walls, fireplace, and large picture windows that frame the surrounding wilderness. Imagine waking up to deer grazing under the apple trees and the melodious chorus of birdsong.

Guest favourite

Cabin in South Kortright

4.91 out of 5 average rating, 245 reviews

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

Ticking all the boxes, this beautiful cabin has everything you could want for your retreat from city life! Five acres of private forest encapsulates the perfect seasonal mood as you step from the great room onto the huge wrap-around deck. Relax and enjoy the property with its hot tub, fireplace, A/C, BBQ grill and poolside loungers. For the adventurous at heart, check out the community shared lake access (non fishing), rivers, hiking trails and ski stations right at your fingertips.

Top Guest favourite

Loft in Prattsville

5 out of 5 average rating, 100 reviews

The Loft at Bearpen Mtn; near Hunter & Windham

Relax in this stylish Mountain View escape at the base of Bearpen Mountain. Hiking trails and snow sports from the front door! Situated near Windham and Hunter; 20 minutes, Belleayre and Plattekill ski mountains, 30 minutes. Walk to winter sports and sledding center. Adjacent to world class trails for hiking, snowmobiling, hunting and skinning. *seasonal rental or multiple stay discounts. $2k per month includes utilities 12/12/25 to 3/15/26 for ski season *no EV charge available

Superhost

Cottage in Denver

4.94 out of 5 average rating, 139 reviews

Country Cottage w/ HOT TUB & Views

Welcome to the most peaceful and tranquil place in the world. Our beautiful home is situated on 3 acres of private land with a private pond and incredible views of the mountains. Escape your life and stressors, and come stay in the fresh air where all you will hear are birds chirping - no sirens, cars or people. The cottage is fully stocked to be enjoyed for all 4 seasons! Relax in the hot tub, or go for a swim in the pond. Our property is the perfect vacation getaway.

Superhost

Home in Bovina Center

4.83 out of 5 average rating, 23 reviews

Luxury Mountain Escape | Breathtaking Views

This stunning home on 10 private acres sits between Bovina Center and Andes, offering sweeping mountain views and luxury amenities. Features include a chef’s kitchen, wraparound sunroom, fireplaces on every level, living room, den, 4 bedrooms (2 en suites), 5 bathrooms, fitness room with Peloton and weights, and a billiards room. Enjoy 3000 sq ft of outdoor deck space. Close to wedding venues and a public pool just 4 miles away—perfect for unforgettable gatherings!