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Vacation rentals with a pool in Windsor County

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor County rentals with a pool

Kitchen
Wifi
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, 94 reviews

Fish, Bike, Golf, or Hike!

Guest favorite
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.
Home in Ludlow
4.91 out of 5 average rating, 104 reviews

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Guest favorite
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

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

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, 45 reviews

Premier Quechee Newton Village Condo: Pet Friendly

Guest favorite
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!

Guest favorite
An open-concept living and dining area features a large wood dining table surrounded by black chairs. A stone fireplace is visible, along with large windows offering natural light. The vaulted wooden ceiling adds warmth, and contemporary light fixtures provide a modern touch.
Home in Killington
5 out of 5 average rating, 5 reviews

Killington Vistas: Luxury 4BR Ski On/Off. Hot Tub.

Guest favorite
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

Superhost
A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.
Condo in Killington
4.93 out of 5 average rating, 176 reviews

Renovated unit, prime location! Shuttle on/Ski off

Superhost
A comfortable living room features a sectional sofa, coffee table, and a flat-screen TV mounted above a fireplace. Natural light flows in through sliding glass doors, revealing a wintery outdoor view. A decorative mirror adds a touch of style to the neutral-toned space.
Condo in Killington
4.83 out of 5 average rating, 70 reviews

Killington Swell Suite: 2RM/2BA Condo|. Pool. 642

Guest favorite
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, 85 reviews

Value in cozy 2 Bedrm only 1/2 mile to Mtn & Apres

Guest favorite
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, 186 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Guest favorite
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

Guest favorite
A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.
Condo in Ludlow
4.93 out of 5 average rating, 114 reviews

One Bedroom Suite Near Okemo

Guest favorite
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

Superhost
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

A spacious living area features a leather sectional sofa and a wooden coffee table, creating a comfortable setting. The flat-screen TV is mounted above a non-operational brick fireplace, surrounded by natural wood paneling. The kitchenette is accessible in the background, offering essential appliances.
Condo in Killington
4.77 out of 5 average rating, 285 reviews

Winter is upon us!

Top guest favorite
Condo in Killington
4.96 out of 5 average rating, 73 reviews

Perfect 2 Bedroom Ski Escape at Killington

Top guest favorite
A multi-story condo building is visible, featuring balconies and a welcoming entryway. Surrounding trees display vibrant fall foliage, enhancing the natural setting. The paved path leads to the building, with an open area of grass adjacent to it.
Apartment in Mendon
5 out of 5 average rating, 15 reviews

Sweet Retreat

Guest favorite
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, 138 reviews

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

Guest favorite
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

Guest favorite
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

Guest favorite
A cozy studio apartment showcases a wood-burning stove located on a brick hearth. A dark sofa is positioned across from a flat-screen TV mounted on the wall. The space is illuminated by sunlight through two windows, draped with sheer white curtains.
Apartment in Thetford
4.98 out of 5 average rating, 41 reviews

Cozy Studio Apartment

Top guest favorite
A warm and inviting fireplace is set into a decorative stone wall. The mantel features various decorative items, including the letters 'Ski,' framed photos, and holiday accents. A potted plant sits beside the fireplace, which is softly illuminated by the flames.
Condo in Killington
4.94 out of 5 average rating, 51 reviews

Pool, Hottub, SPA, Tennis Courts - 2 bedrm/2 bath

Destinations to explore