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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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Home in Killington

4.9 out of 5 average rating, 221 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

4.94 out of 5 average rating, 116 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

4.9 out of 5 average rating, 144 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!

A serene exterior view of the condo is reflected in the calm waters of a scenic pond. Lush green vegetation surrounds the property, with trees providing a natural backdrop. The building features a modern architectural style with large windows and a prominent chimney.

Home in Killington

4.94 out of 5 average rating, 125 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.

An indoor pool area features a bright turquoise pool surrounded by floor-to-ceiling windows, allowing natural light to illuminate the space. Vertical wooden beams add architectural interest, while potted greenery brings a touch of nature indoors. Seating is available in the background.

Condo in Killington

4.88 out of 5 average rating, 147 reviews

Cozy One-Bedroom Ski Home Condo

Ski Home to Trail Creek Close to the mountain Updated 1-level, 1 bed, 1 bth, condo has brand new stainless appliances. Walking distance to Snowshed Base where you can access skiing, biking and the "fun" center. Ski home from Snowshed Slope trail. Steps to the amenities building that houses the pool, hot tub, sauna & exercise area. Wood-burning fireplace, free firewood, in-unit laundry. The view outside is of bucolic woods and a small stream. Killington will not run the shuttle mid-week.

Condo in Killington

4.92 out of 5 average rating, 180 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.

Top guest favorite

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, 199 reviews

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain. check VRBO.1532508 mention this for a better deal

The exterior of a contemporary timber home is visible, featuring a sloped green metal roof and warm wood siding. Surrounding snow-covered ground reflects nearby evergreen trees. The property is situated on a spacious lot, offering a serene winter landscape.

Townhouse in Killington

4.85 out of 5 average rating, 103 reviews

SKI ON/OFF Spruce Glen C | AC | Sauna| Fireplace

Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

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, 180 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.

Condo in Killington

4.9 out of 5 average rating, 104 reviews

Large 1BD/Across from Mtn/Pool/Gym

Enjoy stunning mountain views from this oversized 1BD/1BA condo in Mountain Green Building #3—just a 5-minute walk to Killington Resort and the golf course. Recently updated with a modern bathroom, granite kitchen countertops, new flooring, appliances, and stylish furniture. Dog-friendly and perfect for year-round outdoor fun. Relax after your adventures with a newly installed arcade game for added entertainment! Your perfect Killington escape awaits.

Top guest favorite

Condo in Killington

4.87 out of 5 average rating, 198 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.

Condo in Killington

4.78 out of 5 average rating, 309 reviews

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

Vacation rentals for every style

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Villas

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Cabins

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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

Top guest favorite

A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.

Home in Killington

4.9 out of 5 average rating, 90 reviews

Fish, Bike, Golf, or Hike!

4.91 out of 5 average rating, 23 reviews

Ski-In/Ski-Out Hike Okemo Mountain Condo

A view of a cozy townhouse nestled among colorful autumn foliage. The nearby slopes of Bear Mountain are visible in the background, showcasing the vibrant oranges and yellows of the changing leaves. Neighbors' homes blend into the picturesque mountain landscape.

Home in Killington

4.88 out of 5 average rating, 8 reviews

Luxe 4BR w Incredible View & Game Room!

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, 104 reviews

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Home in Hartford

5 out of 5 average rating, 27 reviews

The Fairway House - Premier Golf Course 3 BR Home

An open living and dining area is highlighted by large windows allowing natural light to fill the space. A wooden dining table with eight chairs is present, alongside a comfortable seating arrangement featuring a sofa and an accent chair. A glamor chandelier hangs overhead, enhancing the welcoming atmosphere.

Home in Hartford

4.93 out of 5 average rating, 43 reviews

Premier Quechee Newton Village Condo: Pet Friendly

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, 62 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, 16 reviews

Private Farmhouse with in ground pool!

Condo rentals with a pool

Top guest favorite

Condo in Killington

4.98 out of 5 average rating, 53 reviews

Luxury Condo - with Garage Parking and Pool

A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.

Condo in Mendon

4.95 out of 5 average rating, 55 reviews

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Top guest favorite

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, 19 reviews

Cozy Slopeside Studio at Pico

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

Condo in Killington

4.93 out of 5 average rating, 80 reviews

PeeP Colors 2 Bedrm only 1/2 mile to Mtn & Apres

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, 114 reviews

One Bedroom Suite Near Okemo

Top guest favorite

An indoor pool area features a large, inviting swimming pool with clear blue water. High ceilings allow natural light to fill the space, while large windows enhance the open feel. Potted plants and wooden accents contribute to a relaxed ambiance.

Condo in Killington

4.97 out of 5 average rating, 149 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

The entrance to the condo features a welcoming blue door, flanked by neatly stacked piles of firewood. A small welcome mat lies at the foot of the door, while a light dusting of snow is visible on the ground.

Condo in Quechee

4.9 out of 5 average rating, 78 reviews

2 Bedroom Condo in Quechee, VT

Other vacation rentals with a pool

Condo in Killington

4.78 out of 5 average rating, 9 reviews

Swirl Suite at Killington: Remodeled 2RM/2BA Suite

A well-maintained outdoor pool area features a rectangular swimming pool surrounded by a paved patio. Red umbrellas provide shade over several lounge chairs, creating a relaxed environment. A small pool house stands nearby, with trees and greenery framing the scene.

Condo in Killington

4.77 out of 5 average rating, 283 reviews

Winter is upon us!

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

An outdoor pool is framed by a secure white fence, surrounded by greenery and lounge chairs. Sunlight reflects off the clear water, while soft clouds hover in the blue sky. A blue cover edges the pool, indicating preparation for use.

Condo in Killington

4.96 out of 5 average rating, 84 reviews

Bright & Cozy Ski Home Condo with Mountain Views

Apartment in Mendon

5 out of 5 average rating, 12 reviews

Sweet Retreat

A comfortable room features a spacious bed with a chevron-patterned comforter and matching pillows. Nightstands with lamps are placed on either side of the bed. A large chest of drawers stands against the wall, adding to the room's cozy and functional design.

Guest suite in Killington

4.94 out of 5 average rating, 17 reviews

The Woods Renovated 1BR Studio close to the slopes

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, 47 reviews

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

Top guest favorite

Apartment in Thetford

4.97 out of 5 average rating, 38 reviews

Cozy Studio Apartment

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