Vacation rentals with a pool in Addison County

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Top-rated rentals with a pool in Addison County

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Guest favorite
A quaint, modern condo is shown amidst a winter landscape, surrounded by snow-covered trees. A wooden deck is visible at the front, complemented by large windows that allow natural light to enter, creating a connection between indoor comfort and outdoor scenery.
Home in Warren
4.83 out of 5 average rating, 127 reviews

Charming Sugarbush Standalone Condo

Situated on the mountain with a panoramic view, this stand alone condo - ski-on/ski-off (winter) / spectacular vistas (fall) / Mad River fun (summer) / blissful bloom (spring) - will be your home away from home. This spacious, three-floored home is filled with light and great for couples, families, business travelers, or solo adventurers. Friendly property manager, Constancia is able to greet guests and offer recommendations. Please find our cleaning protocol in "Other things to note" section.

Top guest favorite
A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.
Guest suite in Starksboro
4.94 out of 5 average rating, 132 reviews

Private Suite in the Green Mountains

Relax in a country setting, centrally located to Vermont attractions. This private apartment in the trees boasts three beds and a full kitchen. With views of the Green Mountains, you will be a short drive away from quaint towns, skiing, breweries, hiking, and swimming. On the property, enjoy the fresh mountain air, changing leaves, and local flora and fauna. In summer, cool off after a hike or bike in the shared pool. In winter, you're 15 minutes to Mad River Glen and 30 to Sugarbush Ski Resort.

Top guest favorite
A welcoming living area is furnished with a navy sofa and a light gray armchair. A low coffee table is positioned on a patterned area rug. Large glass doors provide access to a private balcony, framed by light-colored curtains that softly filter the natural light.
Condo in Warren
4.95 out of 5 average rating, 20 reviews

Cozy Sugarbush condo (Ski in&Ski out!)

Our newly renovated condo has all that you need to unplug and relax, either for ski in and ski out, to enjoy summer at one of the many water holes or an adventurous mountain biking ride or the beautiful foliage during wedding season in Vermont. Perfectly situated, near restaurants, several walking distance like the renowned Chez Henri. Historic Warren is close by with one of our favorite restaurants and bars (Tracks) and of course Sugarbush base is walking distance (or ski “Out to Lunch” down)

Top guest favorite
A living area showcases a comfortable green sofa adorned with decorative pillows. A wooden coffee table holds a board game and a book. Natural light filters through two windows, revealing a glimpse of the outdoor scenery. A small lamp and a potted plant add a touch of greenery.
Condo in Warren
4.95 out of 5 average rating, 22 reviews

NEW 2025 Sugarbush Bridges Resort Outpost

New outdoor HOT TUB Open!! Escape to our fully renovated (2025) 2BR/2BA condo at The Bridges Resort, just minutes from Sugarbush’s Lincoln Peak! Enjoy a brand-new kitchen with stainless steel appliances & filtered drinking water, heated bathroom floors, fully tiled walk-in showers, and a cozy gas fireplace. The primary suite features a queen bed & Smart TV, while the bunk room sleeps four. Relax on the private deck overlooking a creek. WiFi, Xbox, washer/dryer & ski rack. Book your stay today!

Top guest favorite
Two dogs sit calmly in front of a black wood stove, with warm flames visible through the glass door. A decorative arrangement of yellow and brown foliage is placed prominently on a table in the foreground, adding a natural touch to the cozy interior.
Townhouse in Warren
4.96 out of 5 average rating, 23 reviews

Cozy 3-BDR Townhouse with pool, tennis

3 bedroom 2-bathroom sunny end-unit townhouse at Drumleys, with spacious open-air LVR/DR/Kitchen, ski and boot storage, 5 minutes to both Lincoln peak and Mt Ellen, and on the Mad Bus route. Fully stocked kitchen, electric grill for year-round grilling, renovated bathroom with modern full-sized bathtub. Large pool, two tennis/pickleball courts and meadow for summer fun. 1 small-medium house-trained dog allowed. Kate and Greg are superhosts. Meals and Rooms Tax ID number: MRT-10126712.

Top guest favorite
Snow-covered grounds are visible, framed by tall evergreen trees. In the background, a mountain slope is partially visible, marked by ski trails. A white fence and signs of winter's chill set the scene, with cloudy skies overhead.
Condo in Warren
4.97 out of 5 average rating, 137 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Enjoy all the MRV has to offer in our renovated 2 Bedroom, 1 bath condo at the Bridges Resort. The Resort features two outdoor pools, one indoor pool, hot tub, indoor and outdoor clay and Har-Tru tennis and Pickleball courts, updated fitness center, volleyball, basketball, horseshoes, badminton and children's playground. Tennis lessons and clinics available on site. Both gas and charcoal grills are available. Two Fire pits located just outside outdoor. Plenty of convenient parking.

Top guest favorite
A snow-covered slope is flanked by trees adorned with frost, creating a winter wonderland. Skiers can be seen navigating the path under a sky filled with clouds and sunlight filtering through. The serene atmosphere captures the essence of outdoor winter activities.
Condo in Warren
4.91 out of 5 average rating, 74 reviews

Powder Hound Condo

Cozy one bedroom condo in the Mad River Valley, Sugarbush Ski resort and Mad River Glen Ski nearby. Walking trails, shops, restaurants and breweries close by. Deco Bar and Restaurant on-site! Waterbury VT is only 30 minutes where you can find Prohibition Pig Brewery, Cabot Factory annex, Ben and Jerrys Ice Cream Factory and many other place to go. Stowe, VT is 45 minutes, Von Trapp family lodge and brewery, Stowe Cider (personal favorite), Alchemist Brewery and Stowe Ski Resort

Top guest favorite
A vibrant garden surrounds a pool area, featuring blooming tulips and a variety of colorful flowers. A patio umbrella provides shade over seating near the pool, with scenic views of rolling hills and distant mountains visible in the background.
Apartment in Monkton
4.98 out of 5 average rating, 130 reviews

Spacious Private Apartment w/ Green Mountain Views

Guests enjoy views of Camel's Hump & the Green Mountains and beautiful farmland to the East. This space is great for couples & solo adventurers. My home was built in 1810 & the Guest Studio was added onto the house in 1980. Conveniently located midway between Middlebury & Burlington, also a great home-base to take a day trip to the Stowe & the Mad River Valley. Much to explore- visit local farms & apple orchards, great hikes and Lake Champlain, breweries and wineries.

Superhost
A unique concrete structure is set among fallen leaves, showcasing multiple levels and a variety of window shapes. Stairs lead to the entrance, with a wooden door framed by natural surroundings. The building features cantilevered balconies and distinct architectural details.
Home in Warren
4.9 out of 5 average rating, 70 reviews

Concrete Ski House Near Sugarbush

2 Minutes from Sugarbush, Lincoln Peak. Architect Dave Sellers’ “Archie Bunker” is a high-concept concrete manse filled with vintage artifacts. Winner of 2010 American Institute of Architects Award. Includes a private spring-fed swimming pool and golf green for putting and chipping. For a video tour, search "Archie Bunker Offbeat Spaces". Please be sure to read Other Details to Note PRIOR TO BOOKING. THIS IS AN UNUSUAL HOUSE AND ISN'T FOR EVERYONE.

Guest favorite
A spacious living area features large windows allowing natural light to brighten the room, which includes multiple cozy sofas adorned with decorative pillows. A wood-burning fireplace is positioned adjacent to a coffee table, with a dining area and kitchen counter visible in the background.
Home in Warren
4.93 out of 5 average rating, 56 reviews

Ski in/out 3 Bedroom/3 Bath Sugarbush

Wonderful ski-on/ski-off location (natural snow needed) with exclusive and convenient access to Sugarbush Resort's Cat's Meow trail. Renovated 3 bedrooms/3 baths - stand alone unit that sleeps 8. Beautiful wood burning fireplace with stacked wood right outside the front door. Enjoy all that winter has to offer in the Mad River Valley from this fantastic home. In the summer there is a shared pool and tennis courts for the entire family.

Guest favorite
A cozy living area is highlighted by a flat-screen TV displaying Netflix, positioned above a minimalist fireplace. A tabletop showcases two glasses of red wine beside a wooden platter of assorted cheeses and fruit, complemented by flowers in a vase and flickering candles.
Condo in Warren
4.88 out of 5 average rating, 211 reviews

Ski In/Ski Out with upgrades!

Newly renovated with comfort in mind! Brand new Nectar hybrid Queen mattress in bedroom. Lazy boy sofa w/ queen pullout w/ memory foam topper. Large chair in living room w/ large screen TV,Netflix & other channels. Well stocked kitchen, Wifi,books,movies & board games. Bedroom has tv. Located in Sugarbush Village, many restaurants, & activities,within walking distance. First floor unit with easy access.

Top guest favorite
A clear in-ground pool is framed by lush greenery and concrete patios. A shaded area features a table and chairs, while a large umbrella rests nearby. The peaceful setting invites relaxation with calm blue waters reflecting the surrounding landscape.
Cabin in Bridport
4.93 out of 5 average rating, 160 reviews

Champlain Valley Alpacas

Located in central Vermont, our honeymoon cottage is the ideal private getaway, adjacent to in-ground pool (pool available in Vermont season: late June, July- August) ) when you stay with us. You might just be lucky enough to wake up with the alpacas munching outside your window or hear the roosters crowing nearby! Please plan to slip off your shoes at the door.

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