Vacation rentals with a pool in Windsor County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windsor County

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

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Guest favorite

A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.

Condo in Mendon

4.93 out of 5 average rating, 106 reviews

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is conveniently located minutes from Pico & Killington, 🥾AT, 💍wedding venues, 🎓graduations and a variety of local events. Superhost level comfort ready to welcome you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from Long Trail/AT Squeaky Clean Fireplace, TV, WIFI Seasonal Private Pool Private covered porch Keypad check in Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

Guest favorite

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

4.91 out of 5 average rating, 209 reviews

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Guest favorite

A cozy living area is presented, featuring a blue sectional sofa complemented by decorative pillows. A wooden coffee table sits in front, with remote controls arranged on top. Vintage skis are mounted on the wall, adding a rustic charm, while lamps provide soft lighting.

Condo in Killington

4.85 out of 5 average rating, 265 reviews

Comfy ski in/out studio at base of Pico-Killington

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

Guest favorite

An inviting pool with clear blue water is surrounded by a patio. Rolling green hills and a vast sky filled with white clouds create a scenic backdrop. A few lounge chairs and a dining area are positioned nearby, overlooking the tranquil landscape.

Home in Springfield

4.94 out of 5 average rating, 105 reviews

Ski Mountain View Estate

Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Pool is closed for winter

Guest favorite

A fenced outdoor pool area is surrounded by lush greenery and tall trees. The pool is heated and saltwater, reflecting the sunlight. Adjacent to the pool, a small shaded structure provides additional space and amenities.

Home in Plainfield

4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025 (weather dependent. It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything ask!

Superhost

The treehouse design features large windows and wooden siding, surrounded by lush greenery. An expansive deck is equipped with comfortable seating and a fire table, providing a serene outdoor space for relaxation.

Treehouse in Stockbridge

4.94 out of 5 average rating, 118 reviews

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Guest favorite

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

Condo in Killington

4.94 out of 5 average rating, 256 reviews

Wood-Burning Fireplace/Dog-Friendly/Spa Onsite/AC

Escape to tranquility in this charming 2BD, 2BA home, designed with comfort and relaxation in mind. Nestled in a peaceful neighborhood, it’s the perfect retreat for families, couples, and pet owners who want to enjoy a little extra R&R with their furry friends. The spa area with a pool and hot tub (next door) is ideal for unwinding after a long day of exploring or just enjoying the serene environment. Alternatively, you can relax in front of the wood-burning fireplace! New arcade and XboxS!

Top guest favorite

Condo in Killington

4.95 out of 5 average rating, 230 reviews

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

Guest favorite

A cozy living area features a brick fireplace with a warm glow and a skylight that allows natural light to flood the space. Comfortable seating arrangements, including a spacious couch and armchairs, are present, with a coffee table set in the center, enhancing the inviting atmosphere.

Townhouse in Killington

4.97 out of 5 average rating, 115 reviews

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Guest favorite

Condo in Killington

4.9 out of 5 average rating, 129 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

Our cozy two-bedroom condo is just steps from the lifts, spa, ski shops, and restaurants, with a three-minute drive to Killington. Nestled in the Green Mountains, you’ll have access to skiing, hiking, world-class golf, snow tubing, and scenic mountain views. The condo features seasonal amenities including a pool, fitness center, hot tub, sauna, steam room, and more — perfect for both adventure and relaxation!

Guest favorite

A cozy living area features a brick fireplace at its center, surrounded by two comfortable armchairs and a wooden coffee table. A Roku Smart TV is positioned next to large glass doors leading to the balcony, while a mirror reflects the warm ambiance. Natural light enhances the wooden accents on the walls.

Condo in Killington

4.83 out of 5 average rating, 120 reviews

Cozy Condo- Close to Mountain, Ski home trail

Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.

Top guest favorite

A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.

Condo in Killington

4.99 out of 5 average rating, 109 reviews

Cozy Condo - next to Killington Resort

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! King bed and Queen pullout sofa sleeps up to four (4). This property is Shuttle In/Out (Sat & Sun and holiday periods Dec - April). Killington Reg #004858