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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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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

4.9 out of 5 average rating, 217 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!

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

4.95 out of 5 average rating, 112 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

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, 142 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!

Top guest favorite

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

Condo in Killington

4.99 out of 5 average rating, 103 reviews

Elegant Alpine Condo *Pool*

Newly renovated 1-bedroom Whiffletree condo with upscale alpine style, minutes from l bike park, adventure center, and golf course. Please note there is no air conditioning, but the cool mountain air and provided fans typically keep the space comfortable. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool. Easy access to summer fun and scenic Vermont trails. Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718

Top guest favorite

A spacious living area features large windows that provide views of the surrounding greenery. A comfortable sectional sofa, accented with pillows, is positioned near a wooden coffee table. A cozy armchair is placed beside a floor lamp, creating a warm and inviting seating space.

Home in Killington

4.93 out of 5 average rating, 121 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

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

4.94 out of 5 average rating, 111 reviews

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Minutes from Pico & Killington! 🥾AT&LT, 💍wedding venues, 🚴‍♀️mtn. biking, ⛳️ golf 🍁 fall foliage •Rutland Vintage Market is back! 10/10 - 12 - Rutland Fairgrounds OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yr

A spacious backyard features a clear swimming pool bordered by a wooden deck. Colorful flowers accent the landscape, and sun loungers invite relaxation. The two-story residence showcases large windows, blending the indoor and outdoor environments, with an umbrella providing shade beside the pool.

Guest suite in Killington

4.95 out of 5 average rating, 148 reviews

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

Great value! Cozy, clean, SPACIOUS, 3 bedrooms w/4 beds (2 double, 2 twins). You have entire first floor (5 rooms) w/private entrance & private full bath. Sitting area w/ TV & electric fireplace. Dining table. Coffee maker, tea kettle, microwave, toaster, 2 burner counter top stove, charcoal grill (summer), mini fridge. Washer/dryer. Wi-Fi. Indiv heat. Ideal for 4 singles, 2 couples or families w 1-3 kids. Max 5 people. 5 mi. to Killington Rd restaurants, bars, shops, entertainment.

An outdoor swimming pool is presented, featuring clear blue water surrounded by a concrete deck. Poolside seating is visible, along with lush greenery and well-maintained flower beds nearby. A tennis court is seen in the background, adding to the recreational appeal of the area.

Condo in Killington

4.93 out of 5 average rating, 171 reviews

CozyCub - Pool, Hiking, Mountain Biking

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

The indoor pool area features a spacious design with a vaulted wooden ceiling and large windows allowing natural light. A swimming lane runs along the length of the pool, surrounded by lounge chairs and greenery, creating a relaxing environment for guests.

Townhouse in Killington

4.87 out of 5 average rating, 271 reviews

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

Condo in Killington

4.91 out of 5 average rating, 176 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. The shuttle runs daily through the winter season. The indoor pool, hot tub, and gym are open daily. The outdoor pool is open Memorial Day through mid-September.

An outdoor swimming pool is surrounded by a white fence, with a clear blue sky and lush greenery serving as a backdrop. Lounge chairs are positioned along the poolside, and a blue pool cover is rolled up on the edge. Mountains are visible in the distance.

Condo in Killington

4.81 out of 5 average rating, 154 reviews

Charming 3 Bedroom 2 Bath Ski Home/Off

Looking to enjoy all that Killington has to offer in just minutes? Ski home access, a prime location on the shuttle route, and just a 2-minute drive to the slopes, convenience doesn’t get any better. This newly refreshed three-bedroom, two-bathroom condo offers modern comfort and a cozy vibe. After a day of outdoor fun, kick back on the plush sofa and unwind by the warmth of the gas fireplace. It's the ultimate retreat to recharge and enjoy the beauty of Vermont.

An aerial view showcases the condo complex surrounded by lush greenery, featuring multiple buildings arranged along a gravel path. An outdoor pool and a tennis court are visible, with sunlight reflecting off the water. Parking spaces are available nearby for convenience.

Condo in Killington

4.93 out of 5 average rating, 172 reviews

Renovated unit, prime location! Shuttle on/Ski off

We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windsor County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious estate is set against a backdrop of trees, featuring a well-maintained lawn. An inviting in-ground pool is positioned alongside the home, surrounded by lounge chairs. The house is illuminated warmly, reflecting a tranquil evening atmosphere.

Home in Norwich

4.81 out of 5 average rating, 26 reviews

Pond, Pool, Mountain Views | Au Bout du Chemin

Top guest favorite

The kitchen features modern appliances, including a stainless-steel refrigerator and oven. Warm wooden countertops provide a cozy look, with a small dining area adjacent. Natural light filters through two windows, offering views of lush greenery outside.

Home in Hartford

5 out of 5 average rating, 17 reviews

Quaint 2 bedroom Condominium

Home in Killington

Luxe 4BR w/ Fireplace, Game Room & Views!

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

4.91 out of 5 average rating, 101 reviews

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Home in Hartford

5 out of 5 average rating, 26 reviews

The Fairway House - Premier Golf Course 3 BR Home

Top guest favorite

A spacious living area is visible, featuring a dining table set for six and a chandelier overhead. Natural light streams in through large windows, illuminating a cozy seating arrangement with a fireplace in the background. A well-equipped kitchen countertop offers a clear view of the inviting space.

Home in Hartford

4.93 out of 5 average rating, 40 reviews

Bright & Modern Quechee Town House - Self Check-In

The charming yellow home is set against a backdrop of autumn foliage, showcasing green lawns and a wooden fence. A gazebo is visible nearby, inviting relaxation. The structure features a gabled roof and is oriented towards the scenic landscape.

Home in Woodstock

4.97 out of 5 average rating, 61 reviews

Dana Road House Sunlit VT Country Home w/HotTub

An aerial view captures a tranquil backyard featuring a private in-ground pool surrounded by a stone patio. The farmhouse is visible in the background, framed by trees and open lawn space. A shaded seating area and hammock provide relaxation options.

Home in Hartland

5 out of 5 average rating, 14 reviews

Private Farmhouse with in ground pool!

Condo rentals with a pool

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

4.84 out of 5 average rating, 268 reviews

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

The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.

Condo in Mendon

4.88 out of 5 average rating, 112 reviews

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

A spacious outdoor pool area is surrounded by manicured grass. Lounge chairs are positioned around the pool, providing space for relaxation. The building features large windows and multiple decks, blending modern architecture with a natural setting.

Condo in Killington

4.96 out of 5 average rating, 138 reviews

Dog-Friendly Mtn Escape/AC/Pool/

An indoor swimming pool is surrounded by large windows, allowing natural light to fill the space. Comfortable seating areas with dark woven chairs are set nearby. The pool features steps leading into the water, with a relaxing hot tub positioned at one end.

Condo in Killington

4.96 out of 5 average rating, 72 reviews

Perfect 2 Bedroom Ski Escape at Killington

A spacious living area is highlighted by a comfortable gray sofa and a wooden coffee table. Natural light streams through large windows, complementing the warm wood paneling that separates the sleeping nook. A flat-screen TV and a cozy seating arrangement add to the inviting ambiance.

Condo in Killington

5 out of 5 average rating, 18 reviews

Cozy Slopeside Studio at Pico

Top guest favorite

Condo in Killington

4.95 out of 5 average rating, 247 reviews

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

An indoor pool area is highlighted by a spacious swimming pool. Natural light enters through large windows, offering views of the outdoor patio. Seating areas with chairs are arranged along the walls, complemented by warm-toned curtains.

Condo in Ludlow

4.93 out of 5 average rating, 111 reviews

One Bedroom Suite Near Okemo

A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.

Condo in Killington

4.93 out of 5 average rating, 198 reviews

Newly renovated ski retreat at Killington

Other vacation rentals with a pool

An inviting living area features comfortable sofas and an orange armchair. A wooden coffee table is positioned centrally, with a fireplace adorned by a brick wall as a focal point. Natural light streams in through large windows, illuminating the warm interior.

Townhouse in Hartford

4.88 out of 5 average rating, 66 reviews

Ski-in Ski-Out Cozy Mountainside Condo

A well-maintained outdoor swimming pool is framed by a sleek wooden railing, surrounded by lush greenery. The black lodge in the background is complemented by the clear blue sky, creating a serene atmosphere. Lounge chairs are positioned nearby for relaxation.

4.92 out of 5 average rating, 38 reviews

Hilltop 9-BR Mountain Retreat 5-min to Okemo

An indoor pool area is featured, with a spacious swimming pool lined by blue lounge chairs. Large windows allow natural light to fill the room, enhancing the bright atmosphere. The covered structure showcases a high ceiling, ensuring a comfortable swimming experience year-round.

Villa in Brownsville

4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

The living room features a Joybird sectional sofa, a coffee table, and a vibrant area rug. A television is mounted above a turquoise fireplace. Shelving displays books and decorative items against a white brick wall, while a dining area with green cabinetry is visible in the background.

Condo in Killington

5 out of 5 average rating, 11 reviews

Stunning Slopeside Condo at Mountain Green: 1BR

An aerial view captures the modern townhouse nestled among vibrant autumn foliage, with ski slopes visible in the background. The property features a private pool and is surrounded by well-kept landscaping, showcasing the picturesque setting for outdoor activities.

Townhouse in Killington

5 out of 5 average rating, 45 reviews

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

A cozy living area features exposed beam ceilings and wood floors. Two comfortable sofas face each other, complemented by a coffee table and side tables with lamps. A staircase leads to the upper level, and a small workspace with a chair is visible in the corner.

Cabin in Hartford

4.97 out of 5 average rating, 73 reviews

Cozy Quechee Corner Cabin

A spacious bedroom showcases a king bed with balanced bedding, complemented by a flat-screen TV on a light-colored dresser. Natural light pours through the window, which is adorned with soft blinds, creating a bright atmosphere.

Condo in Killington

4.85 out of 5 average rating, 13 reviews

Beautifully renovated spacious 2 room 2 BA suite

The open-concept living area features a cozy seating arrangement with a large sectional sofa and a rustic wooden coffee table. A stone fireplace is situated against a feature wall, complemented by various wooden accents and a dining area with a large table fitted with upright chairs.

Apartment in Ludlow

5 out of 5 average rating, 7 reviews

Cozy Mountain-Style Condo Near the Slopes

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