Vacation rentals with a pool in Windsor County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Windsor County rentals with a pool

House rentals with a pool

Guest favorite
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
4.91 out of 5 average rating, 204 reviews

Luxury Condo Tucked in the Heart of Killington

Anil KumarRating, 5 stars3 days ago
The place was amazing. Probably one of the best Airbnb’s I’ve rented in terms of value for money. Very responsive host. The location is private, had pretty much all the amenities one needs and everything was well organized. The only downside is the check in is at 3pm but the checkout is at 10am. Which is pretty much unheard of. I’ve asked for one hour extension but was immediately sent a 25$ surcharge request for 1 hour. Apart from that everything was good.
Top guest favorite
The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.
Home in Mendon
4.89 out of 5 average rating, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars2 weeks ago
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!
Superhost
A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.
Home in Hartford
4.8 out of 5 average rating, 10 reviews

Pet-Friendly, Mountainside Home | Treetop Lodge

AnneRating, 5 stars5 months ago
We stayed here while visiting family in Hanover forThanksgiving. A spacious house nestled within an amazing wooded area. We had the pleasure of waking up to all the trees covered in fresh snow. All the more perfect because the house has huge windows lots of natural light. Highly recommend.
Top guest favorite
A modern living space features a sectional sofa adorned with various cushions, complemented by a sleek coffee table. Natural light filters through the windows, highlighting the plant and decorative items, while a piece of abstract art decorates the wall.
Home in Rutland
5 out of 5 average rating, 10 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars1 month ago
The stay was excellent. The home was beautifully renovated. The rooms were large and very comfortable. Location was perfect for the 8 of us for a ski weekend at Killington. Hope to be back.
Superhost
A spacious sunroom features large windows that flood the area with natural light. Comfortable seating includes a floral-patterned sofa, an armchair, and a rocking chair arranged around a coffee table atop a vibrant area rug. Exposed brick walls add texture to the inviting space.
Home in Landgrove
4.75 out of 5 average rating, 28 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

JadeRating, 5 stars8 months ago
Beautiful home and cottage with stunning surrounding scenery. Came here on a getaway from NYC and it was exactly what we needed. The jumbo jet bathtubs and fireplaces give this cozy space a luxurious feel, and the kitchen was downright impressive (brought a chef friend for us who was very impressed). Had to call the host with some questions when I arrived but they were answered immediately. Very clear check in instructions from the host and once we pulled up to the property it was very seamless to get inside and begin unpacking. We had an stress-free stay and checkout thanks to the intention with which these hosts set up their space and rental process. We will be coming back next year!
Superhost
Home in Hartford
5 out of 5 average rating, 25 reviews

The Fairway House - Premier Golf Course 3 BR Home

JanetRating, 5 stars19 months ago
We thoroughly enjoyed our stay with 5 adults and one dog. We walked in and immediately felt at home. This was one of the most well appointed places I have ever rented...it had everything we needed and more . The kitchen and the living space was quite comfortable. The beds were wonderful. There is a trail to the river right across the street which we used several times. I can't think of a negative thing to say.
Top guest favorite
The exterior of the condo showcases a modern design with a symmetrical facade. Large windows allow natural light into the interior, while a charming porch is framed by greenery and trees, providing a welcoming entrance.
Home in Hartford
4.92 out of 5 average rating, 38 reviews

Bright & Modern Quechee Town House - Self Check-In

GailRating, 5 stars1 month ago
We loved it! Great description and photos, really accurate. Michael was so helpful and really friendly and responsive.
Guest favorite
A spacious fenced pool area features a rectangular swimming pool surrounded by a paved patio. Two lounge chairs are positioned nearby, and a small shed is visible in the background. Green hills stretch out beyond the pool, showcasing a natural landscape.
Home in Hartland
5 out of 5 average rating, 10 reviews

Private Farmhouse with in ground pool!

ChrisRating, 5 stars8 months ago
My family and I truly enjoyed our time spent at the farmhouse. Everything was as expected from the listing. The pictures do not do justice for the property. It's beautiful and well maintained. The pool was nice, warm, and clean. There are yard games readily available and a nice fire pit area. Brin and Maria are super responsive and left very detailed instructions on the property for you. Everything you need is there minus food, which is a 12-minute drive towards a few different grocery stores. The hill is so fun to roll down, too! Thank you so much!

Condo rentals with a pool

Guest favorite
An indoor pool area features a clear blue pool surrounded by tile flooring. Natural light enters through tall windows, creating a bright atmosphere. Vertical wooden beams and greenery enhance the open space, providing a welcoming area for relaxation.
Condo in Killington
4.95 out of 5 average rating, 20 reviews

Northlands at Trail Creek

ClintRating, 5 stars1 month ago
Super wonderful spot that is walkable to lifts and then able to ski home at the end of the day. There's a great sauna , hot tub and pool right around the corner from the condo. All super convenient. Will be back next year.
Top guest favorite
An outdoor pool area is shown, featuring a spacious swimming pool surrounded by lounge chairs. Bright red umbrellas provide shade, and a nearby building with multiple balconies is visible in the background. The pool's water reflects clear blue skies.
Condo in Killington
4.86 out of 5 average rating, 84 reviews

Mountain Oasis

CynthiaRating, 5 stars1 month ago
Cozy, clean, well appointed condo with great amenities within walking distance of the mountain, wonderful!
Guest favorite
An indoor recreation area is shown, featuring a small pool at the center. Natural light enters through large windows, illuminating the space. Green plants are placed strategically around the walls, while a seating area is visible in the background.
Condo in Killington
4.91 out of 5 average rating, 141 reviews

2 bed-2 bath (6 max): walk to lifts and lodges

CharlesRating, 5 stars1 month ago
A wonderful home base for a wonderful Winter ski treat! Highly recommended, very comfortable and very well equipped. Super smooth check-in in a wonderful location.
Guest favorite
Condo in Killington
4.9 out of 5 average rating, 128 reviews

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

KateRating, 5 stars2 weeks ago
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!
Guest favorite
The exterior of a multi-story condo building is highlighted, featuring warm wooden siding and large windows. Lush green trees frame the front, and a clear blue sky adds to the setting's openness. The surrounding area includes well-maintained landscaping.
Condo in Killington
4.91 out of 5 average rating, 23 reviews

Pico Mountain Ski in and Ski out

RobinRating, 5 stars2 months ago
“Michele is a wonderful host! The location was perfect—just a short drive to Killington Mountain and the added bonus of being able to walk right onto Pico Mountain made our trip even better. The convenience and ease of access to the slopes made for an amazing stay. Highly recommend!”
Guest favorite
A resort-style pool area is surrounded by lounge chairs and umbrellas, set against a backdrop of condominium buildings. The pool features a clean, inviting design, with steps leading into the water. Paved surfaces create a spacious atmosphere for relaxation.
Condo in Killington
4.83 out of 5 average rating, 175 reviews

Skier's Retreat 2bed/1.5 bath condo w/ Amenities

BenRating, 5 stars1 month ago
This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it
Superhost
An indoor swimming pool is depicted with clear blue water, featuring multiple lanes marked by buoy lines. Surrounding areas include seating and wood-paneled walls, providing a spacious and inviting atmosphere for relaxation and recreation.
Condo in Killington
4.82 out of 5 average rating, 257 reviews

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

ZacharyRating, 5 stars2 months ago
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.
Top guest favorite
An outdoor heated pool is set within a well-maintained garden, surrounded by lounge chairs and shaded by umbrellas. Lush greenery frames the area, enhancing the inviting atmosphere of the resort. A charming building with multiple windows is visible in the background.
Condo in Ludlow
4.96 out of 5 average rating, 51 reviews

3 Bedroom Castle Town Home

TomRating, 5 stars1 month ago
For our family of three this home fit us perfectly. You CAN certainly have more guests but it truly fit our needs. The set up was VERY spacious and cozy at the same time. The women at the desk are so kind and very good at their jobs. Not only did we feel at home when we arrived to our place, meeting them made us feel even more welcome. The castle was exquisite and an amazing experience in itself. The quaint town of Ludlow is a heart beat away with everything you need. All and all we can't say enough about how satisfied we are with Andy's home, the pricing, the staff and location! Our experience was amazing, memorable and we will be returning for sure next year! We are planning to come with our best friends next year & their kids because of your amazing home & our fantastic experience! 😁 Thank you again for opening your home to our family! The Baers

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