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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, 220 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, 114 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, 143 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 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

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

Townhouse in Killington

4.77 out of 5 average rating, 111 reviews

SKI ON/OFF Spruce Glen B | 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, 177 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.

A living room is furnished with a comfortable brown sofa and an armchair beside a wooden coffee table. A rustic wooden fireplace is adorned with festive garland and a flat-screen TV is mounted above it. Natural light enters through a large window, providing a cozy ambiance.

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!

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

4.92 out of 5 average rating, 173 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.

An indoor pool area is illuminated by natural light streaming through large windows and skylights. The pool's surface reflects the blue and white tones of the decor, enhancing the spacious feel of the room. Elegant wall sconces add soft lighting to the atmosphere.

Condo in Ludlow

4.95 out of 5 average rating, 101 reviews

Winterplace - Steps away from Slopes

Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

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, 120 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!

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

4.98 out of 5 average rating, 121 reviews

Cozy Condo *AC & Pool *

Bright, updated 1-bedroom Whiffletree condo in the heart of Killington—just minutes from the bike park, adventure center, and golf! Cool off in the outdoor pool and enjoy air conditioning for those warm summer days. Fully stocked with all the essentials plus a gear locker. Sleeps up to 4 with a king bed and queen pullout sofa—your perfect summer getaway! Killington Reg #004858

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

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, 27 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

A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.

4.9 out of 5 average rating, 21 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

4.75 out of 5 average rating, 4 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

Top guest favorite

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, 40 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, 61 reviews

Dana Road House Sunlit VT Country Home w/HotTub

Condo rentals with a pool

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

Top guest favorite

Condo in Killington

4.95 out of 5 average rating, 251 reviews

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

A spacious lawn features well-maintained green grass, surrounded by lush trees and shrubs. Comfortable seating options are provided with classic outdoor chairs positioned near a flower garden, inviting relaxation in a serene, private outdoor space.

Condo in Quechee

4.88 out of 5 average rating, 93 reviews

Condo on Quechee Golf Course with Private Feel

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, 112 reviews

One Bedroom Suite Near Okemo

Condo in Killington

4.94 out of 5 average rating, 96 reviews

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

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

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

Condo in Killington

4.97 out of 5 average rating, 148 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Other vacation rentals with a pool

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, 279 reviews

Come to Killington this summer!

An open living area is showcased, featuring a leather sofa in a neutral tone and a rustic wooden coffee table. A mounted television is positioned above a cozy stone fireplace. The adjoining kitchen area is visible, along with a wooden dining table that seats four.

Condo in Killington

4.7 out of 5 average rating, 115 reviews

Killington Tree House: 2 Room Modern Condo 432

Top guest favorite

A living room features a large, wall-mounted TV displaying streaming options, situated above a white-brick fireplace. Cozy leather sofas are arranged around a wooden coffee table. The wall is adorned with wood paneling, providing a warm ambiance, while soft lighting enhances the inviting space.

Condo in Killington

5 out of 5 average rating, 17 reviews

Golf Fish Hike Bike Vemont Foliage season!

Condo in Killington

4.96 out of 5 average rating, 170 reviews

Cozy 3 Bed/2 Bath on Killington

A spacious living area is highlighted by two comfortable sofas and a rustic coffee table. Natural light filters through patio doors, illuminating a cozy seating arrangement. Vintage skis are displayed on the wall, adding character to the inviting space.

Apartment in Mendon

4.92 out of 5 average rating, 61 reviews

Charming Killington get away with pool, sleeps 4

Top guest favorite

An inground pool is featured in a fenced-in area, surrounded by greenery. A slide is attached to one side, and steps lead into the water. The pool deck provides ample space for lounging, with a view of the nearby trees and shrubs.

Home in Chittenden

4.91 out of 5 average rating, 94 reviews

Comfortable, relaxing large country home

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, 77 reviews

2 Bedroom Condo in Quechee, VT

A spacious room is highlighted by large windows, allowing natural light to brighten the area. Two comfortable chairs are positioned near a decorative coffee table, while an extensive library of books fills the walls, creating an inviting and relaxed reading environment.

Home in Hanover

4.67 out of 5 average rating, 12 reviews

Large Dartmouth College Home w/ Outdoor Pool

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