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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, 90 reviews

Fish, Bike, Golf, or Hike!

Guest favorite
Home in Ludlow
4.91 out of 5 average rating, 23 reviews

Ski-In/Ski-Out Hike Okemo Mountain Condo

Guest favorite
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!

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
Home in Hartford
5 out of 5 average rating, 27 reviews

The Fairway House - Premier Golf Course 3 BR Home

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, 42 reviews

Premier Quechee Newton Village Condo: Pet Friendly

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 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

Superhost
A cozy living area is presented, featuring a blue sectional sofa complemented by decorative pillows. A wooden coffee table sits in front, with remote controls arranged on top. Vintage skis are mounted on the wall, adding a rustic charm, while lamps provide soft lighting.
Condo in Killington
4.84 out of 5 average rating, 269 reviews

Comfy ski in/out studio at base of Pico-Killington

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

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, 80 reviews

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

Guest favorite
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

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

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, 282 reviews

Winter is upon us!

Guest favorite
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

Guest favorite
Apartment in Mendon
5 out of 5 average rating, 12 reviews

Sweet Retreat

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
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

The entry sign for The Pointe at Castle Hill Resort & Spa is prominently displayed, surrounded by well-maintained greenery and shrubs. A backdrop of trees is visible, contributing to a serene setting under a partly cloudy sky.
Condo in Cavendish
4.75 out of 5 average rating, 63 reviews

Hotel Standard Condo Minutes from Okemo

Destinations to explore