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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, 223 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!

The exterior of a charming yellow house is surrounded by lush greenery and colorful landscaping. A stone pathway leads to the entrance, framed by well-maintained shrubs and ornamental features. Tall trees provide privacy and a natural backdrop, enhancing the serene outdoor atmosphere.

Home in Plainfield

4.9 out of 5 average rating, 145 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 features a large dark sectional sofa, complemented by decorative pillows. A wooden coffee table sits in front, and a sleek fireplace is located within the wooden mantel. Large windows allow natural light to brighten the space, framed by gray curtains.

Townhouse in Killington

4.93 out of 5 average rating, 291 reviews

Modern Mountain Condo with Spa, Pool, Sauna, Gym

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.

Condo in Killington

4.92 out of 5 average rating, 183 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, 201 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

A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.

Condo in Killington

4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

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, 183 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.

Top guest favorite

A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.

Condo in Killington

4.97 out of 5 average rating, 149 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

Condo in Killington

4.78 out of 5 average rating, 310 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!

Top guest favorite

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

Condo in Killington

4.96 out of 5 average rating, 148 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

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

4.84 out of 5 average rating, 141 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.

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Quaint homes, peaceful surroundings

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, 93 reviews

Fish, Bike, Golf, or Hike!

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.

4.91 out of 5 average rating, 23 reviews

Ski-In/Ski-Out Hike Okemo Mountain Condo

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

A two-story condo features a warm wood exterior surrounded by lush greenery. Multiple deck chairs are arranged on the patio, inviting relaxation. Large windows provide ample natural light, showcasing the peaceful setting among trees and well-maintained grass.

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, 45 reviews

Premier Quechee Newton Village Condo: Pet Friendly

Top guest favorite

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, 17 reviews

Private Farmhouse with in ground pool!

A cozy living room features two white slipcovered sofas opposite a traditional brick fireplace, which is glowing with a warm fire. Natural light enters through several windows, complemented by minimalistic decor including a floor lamp and a woven basket.

Home in Hartford

4.95 out of 5 average rating, 22 reviews

Farmhouse, Fireplace & Office - Wheelock Hideaway

Condo rentals with a pool

Top guest favorite

Condo in Killington

4.96 out of 5 average rating, 72 reviews

Perfect 2 Bedroom Ski Escape at Killington

Condo in Killington

4.9 out of 5 average rating, 70 reviews

The Big Chillington Sleeps 6 in Killington Center

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, 84 reviews

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

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

Condo in Ludlow

4.95 out of 5 average rating, 102 reviews

Winterplace - Steps away from Slopes

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, 94 reviews

Condo on Quechee Golf Course with Private Feel

A ski resort property is depicted, featuring multiple gray wooden buildings with distinct gabled roofs. Balconies are visible on some units, and a gentle slope is seen in the background, hinting at the nearby mountain scenery. Clear skies suggest a bright, sunny day.

Condo in Killington

4.82 out of 5 average rating, 257 reviews

Ski, Ride, Walk On/Off Condo On Pico at Killington

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

A living area features wooden walls and a stone fireplace, creating a cozy atmosphere. A dining table with four chairs is positioned adjacent to a comfortable seating arrangement. Natural light floods in through sliding glass doors that lead to a balcony.

Condo in Killington

4.84 out of 5 average rating, 75 reviews

Snowshed, Ramshead Ski Lodges in walking distance!

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, 68 reviews

Ski-in Ski-Out Cozy Mountainside Condo

The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.

Condo in Killington

4.9 out of 5 average rating, 137 reviews

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

Top guest favorite

A cozy living area is outfitted with a comfortable sofa and two leather chairs. A coffee table sits in front of a fireplace, while a flat-screen TV is mounted above the mantel. A large window offers views of the outdoors, allowing natural light to fill the space.

Condo in Ludlow

5 out of 5 average rating, 17 reviews

True Ski in/Ski out with Pool, Hot tubs & Firepits

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

The exterior of the townhouse showcases a two-story structure with a sloped roof and large windows. A wooden deck features seating for two, inviting relaxation outdoors. Surrounding greenery complements the setting, while a stone path leads to the entrance.

Townhouse in Killington

5 out of 5 average rating, 48 reviews

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

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, 64 reviews

Charming Killington get away with pool, sleeps 4

A green directional sign indicates the Trail Creek Ski Home Trail. The sign is mounted on a tree, surrounded by bare branches that indicate a winter setting, with light snow on the ground.

Condo in Killington

4.9 out of 5 average rating, 70 reviews

1BR Ski-Home Pool/HotTb, Walk 2 Lifts, golf

A comfortable living area is furnished with two sofas, a coffee table, and a wooden console table. A stone fireplace serves as a focal point, flanked by decorative items. Large windows provide natural light, while red curtains add a pop of color to the neutral decor.

Apartment in Killington

4.92 out of 5 average rating, 36 reviews

Ski home to your front door! 2 bedroom unit.

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