Vacation rentals with a pool in Greene County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greene County

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

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Guest favorite

Cabin in Shandaken

4.95 out of 5 average rating, 143 reviews

Cozy 4Br Retreat: Heated/Saltwater Pool Open 5/8

Pool Opens May 8th! Newly renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. *Fully private* (small houses are sheds) A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-mid Sept). Our newly added 6 person hot tub is available year round. It's the perfect spot for a much needed recharge with family and friends.

Jul 1 – 8

R16,584 ZAR per night

Guest favorite

Townhouse in Hunter

4.9 out of 5 average rating, 115 reviews

Gorgeous Mountain View | Ski/Fast Wi-Fi/Wood Stove

Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

May 28 – Jun 4

R2,423 ZAR per night

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 111 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Apr 11 – 18

R3,221 ZAR per night

Guest favorite

Home in Catskill

4.95 out of 5 average rating, 175 reviews

Daydream Mountain Art-Chateau '73 | I ❤️ Catskill

Our home is perched on a hill with a panoramic view of the Catskill Mountains. The vista is magical in every season. This home is designed to be an oasis for relaxation, fun and art! Perfect location to access beautiful hiking, skiing, swimming and life-affirming nature, yet also close to towns and restaurants. Short drive to Catskill, Hudson and Woodstock. Stocked with instruments, toys, supplies, books, games, and ping pong. In the Summer you can enjoy the pool and the hot tub year around!

Jun 10 – 17

R12,836 ZAR per night

Guest favorite

Condo in Windham

4.95 out of 5 average rating, 22 reviews

Lovely stylish 2-bedroom condo with community pool

Located minutes away from the Windham mountain, this stylish yet family-friendly condo at Windham Quads has it all! Enjoy the community pool and 2 tennis courts or relax on the porch in the summer, warm up by the wood-burning fireplace after hitting the slopes in the winter, use the WiFi for work or leisure. The town of Windham, with its' fabulous cafes and restaurants is just 3 minutes away. If you enjoy skiing, hiking, mountain biking or golfing, my place will be a great getaway for you!

Apr 12 – 19

R2,780 ZAR per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 133 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Aug 21 – 28

R1,749 ZAR per night

Guest favorite

Townhouse in Hunter

4.91 out of 5 average rating, 136 reviews

Spring into a Dynamic Stay at an Ideal Hunter Home

Classic Townhome- w/ Classic feel. SPRING SPECIALS Centrally located spacious getaway with simple contemporary style with classic comfort w/ amazing views owned and operated by AIRBNB Super Host and NY Native. 2 min drive or a 15 min walk to Hunter Mtn. Next to the boutique Scribner Lodge and their amazing restaurant. Hiking, biking, BBQ & breathe in the views and enjoy 2 stone fireplaces OR the outdoor fire pit Bedroom A/C's. Great for a family getaway or few days out of town w/ friends.

May 12 – 19

R1,686 ZAR per night

Guest favorite

Apartment in Windham

5.0 out of 5 average rating, 17 reviews

Black Dome - a 2B, 2B Condo 5 min from Windham Mt.

Experience ultimate comfort in our renovated, 2 story condo in the Catskills. With 1,000 sq ft of modern style, it boasts mountain views. Upstairs, find two cozy bedrooms with plush bedding for a restful sleep. The fully-equipped kitchen features top-notch appliances, perfect for any culinary needs. Unwind in the living room with high-speed wifi and a cozy fireplace. Step out onto a spacious back deck overlooking Elm Ridge forest. Located minutes from Windham Path, Mountain, and town.

Jun 14 – 21

R2,444 ZAR per night

Superhost

Townhouse in Windham

4.82 out of 5 average rating, 177 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Modern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Complex amenities include outdoor pool (open from Memorial Day through Labor Day) 2 tennis courts and a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!

Sep 2 – 9

R3,341 ZAR per night

Guest favorite

Apartment in Earlton

4.93 out of 5 average rating, 279 reviews

Sweet Farm Stay

Come stay in our renovated barn apartment with a views that look out over the pony paddock and the sheep pasture! We are located in Greene County, just 2.5 hours from the city. For an extra fee we also offer… ** FARM CAMP** perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning that you are here. Look for us on ig — honeyhollowfarmstay — to see what we do in camp and why we have so many repeat visitors! 😍

Jan 15 – 22

R5,409 ZAR per night

Guest favorite

Condo in Tannersville

5.0 out of 5 average rating, 34 reviews

Modern 3BR Townhouse Minutes from Ski & Trails

Cozy townhome with wood-burning fireplace just minutes to restaurants, breweries, hiking trails, mountains, and waterfalls. Skiier's paradise: 5-minute drive to Hunter Mountain, 20-minute drive to Windham Mountain, and 35-minute drive to Belleayre Mountain. Hikers and food enthusiasts can enjoy year-round. The home has beautiful mountain views from the front balcony with space to relax on a large sofa with forest views on the back deck.

Aug 7 – 14

R2,610 ZAR per night

Guest favorite

Home in Catskill

4.93 out of 5 average rating, 164 reviews

The Grandview | Catskill, NY

Guest will be greeted with crisp, clean linens, extra comfy bedding, and a spacious atmosphere pleasantly appointed to ensure a cozy stay. The Grandview is a 5 Bedroom 2 Bathroom property that has been appointed specifically for Airbnb guests. This 1890’s Victorian has been offers both old world charm and modern amenities throughout. We're happy to have you enjoy the space as much as we do.

Aug 7 – 14

R14,680 ZAR per night