Vacation rentals with a pool in Killington

4.88 out of 5 average rating, 106 reviews

A serene outdoor area is featured, showcasing a private heated pool surrounded by a brick patio. Lush greenery defines the background, and a rustic wooden table with chairs sits nearby, providing a space for relaxation in nature.

Chalet in Winhall

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

BrandonRating, 5 stars1 month ago

Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!

Top guest favorite

Home in Killington

4.93 out of 5 average rating, 107 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

MattRating, 5 stars1 week ago

The condo was very nice and just like it was described. Easy to find everything, quiet neighborhood and great for dogs. The sauna was a great amenity, made the trip even more relaxing. The condo was close to downtown and easy access to the local restaurants, shops and outdoor activities. Would definitely stay again

4.98 out of 5 average rating, 46 reviews

The image captures a winter scene featuring a steaming outdoor heated pool surrounded by snow-covered grounds. In the background, a clock tower with a tall spire is visible, with evergreen trees framing the setting, contributing to a serene atmosphere.

Condo in Stratton

A Village location, Steps to the Lifts & Village

LelahRating, 5 stars1 month ago

We loved staying at this property. The location is excellent for access to the village and the lifts. It is also cute to look out over the ice skating pond. It was clean, had all the kitchen amenities you would need to make food, and had fun ski-oriented decorations. It is also close to the hot tub and lounge area within the main building. It had everything we needed to make out ski weekend comfortable and memorable. Can't wait to stay again!

4.87 out of 5 average rating, 39 reviews

An elevated view captures a blue pool surrounded by lush greenery. Trees frame the scene, and soft clouds drift above, creating a serene backdrop. A wooden deck leads to the pool, inviting relaxation and enjoyment within this natural setting.

Home in Ticonderoga

4 BR/2BA Downtown Ticonderoga

JeniRating, 5 stars6 months ago

We had such a great time at Ashley's place and really appreciated the welcome basket & being able to bring our 2 kitties with us to stay that need meds. (We also loved the neighborhood porch kitty that visited daily.) Thank you SO much, Ashley!

4.73 out of 5 average rating, 11 reviews

The inviting pool area is surrounded by a sleek railing, offering views of the lush green landscape and the cabin in the background. Sunlight reflects off the clear water, creating a serene ambiance for relaxation.

Cabin in Ludlow

Contemporary 4-BR Cabin 5-min to Okemo

LaurajeanRating, 5 stars8 months ago

Meadow’s home was lovely and just what we were looking for! It was both comfortable and spacious enoughto spread out when needed but also felt very cozy. The pool was clean and a definite plus for my 2 grandchildren, who were out in it day and night! The location was private but close to stores and restaurants. We would certainly recommend and stay here again. Meadow was very responsive to all of our questions (and we had a few!). Thanks, Meadow.

4.9 out of 5 average rating, 894 reviews

A swimming pool is surrounded by lush greenery, inviting relaxation and enjoyment. The clear blue water reflects the surrounding landscape, providing a refreshing appeal. A person is seen in the water, engaged with a floating device, highlighting the leisure activities available at the property.

Guesthouse in Granville

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 starstoday

There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

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.

4.93 out of 5 average rating, 197 reviews

Newly renovated ski retreat at Killington

YangRating, 5 stars2 weeks ago

Wayne is super nice, friendly, and responsive. He gave me heads up note on check-in day when the main road (Killington Access Road) was closed due to downed trees&wires. He also helped me confirm the parking spot in late night when I arrived late. The place is cozy and clean. There’s a number of good restaurants and taverns nearby.

4.98 out of 5 average rating, 191 reviews

A serene backyard features a heated saltwater swimming pool, surrounded by lounge chairs and a safety fence. Verdant landscapes and a blue sky provide a tranquil backdrop, while a red barn is visible in the distance, adding to the rural charm.

Home in Salem

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 months ago

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

4.97 out of 5 average rating, 147 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

EileenRating, 5 stars1 month ago

Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.

An indoor pool area features large windows that bring in natural light, showcasing winter scenery outside. Comfortable lounge chairs and a table with an umbrella are arranged around the pool, creating a serene space for relaxation.

4.96 out of 5 average rating, 27 reviews

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC

ChrisRating, 5 stars2 weeks ago

What a great place. It was very enjoyable for the whole family. There were plenty of board games, and an arcade game (packman along with many other old game's to choose from). It was sleek, it was spotless and had everything we needed. We loved the area and spa. Thanks and we will hopefully see your great place again soon.

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What guests are saying

Charming Barre Getaway

4.94 out of 5 average rating, 67 reviews1 month ago

The best stay around! Barre is a great little walkable town with shops and restaurants to explore. It’s only a short drive to local ski / snowboarding mountains as well as some hiking. The house was clean, spacious and very nicely decorated. The kitchen had everything we needed that made it feel like we were cooking right at home, which we loved. Karen and Courtney were responsive and very helpful!

Home in Barre

What guests are saying

Prime Ski-in/Ski-out @ PICO Mtn

4.97 out of 5 average rating, 29 reviews2 months ago

We had an amazing stay at Simone’s apartment for our ski vacation. The apartment was even better than the pictures—spacious, clean, and equipped with everything we needed. The location made skiing incredibly convenient, with easy in-and-out access to the slopes. The host was fantastic—super helpful, responsive, and easy to communicate with, which made everything smooth from check-in to check-out. The place had all the essentials and more, making it feel like a home away from home. Very thoughtful touches from the host through the apartment !!!! Highly recommend this place for anyone ( with kids, no kids) looking for a hassle-free and comfortable ski trip. We’ll definitely be back!

Condo in Killington

What guests are saying

Ski & Spa Winter Escape

4.83 out of 5 average rating, 53 reviews3 weeks ago

Melissa's place was great for our group of 4 friend group skiing at Killington over the weekend! It was super easy to get to Killington to ski and cozy to come home to after a day on the slopes. We didn't get a chance to use the hot tub/spa but certainly would love to next time!

Condo in Killington

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Vacation rentals for every style

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Adventure-ready homes with après-ski style

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Kick off your hiking boots at these rustic lodgings

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Quaint homes, peaceful surroundings

Popular amenities for Killington rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 202 reviews

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

Luxury Condo Tucked in the Heart of Killington

AshleyRating, 5 stars2 weeks ago

Comfortable and convenient location. Everything we needed was in the kitchen. We had most of our meals in and took advantage of the kitchen. The sleeping accommodations were very comfortable. It is only a short drive to Killington, where my family skied. We would definitely stay there again.

4.96 out of 5 average rating, 141 reviews

A serene landscape showcases smooth, multicolored rocks along the edges of a gently flowing river. Surrounded by lush greenery, the water reflects the surrounding foliage, creating a tranquil natural setting. The sound of flowing water enhances the peaceful atmosphere of the scene.

Home in Granville

Epic Views of the Green Mountains

StephenRating, 5 stars3 weeks ago

Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!

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 stars1 week 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!

4.96 out of 5 average rating, 25 reviews

A well-maintained outdoor pool area features a clear blue water pool surrounded by lounge chairs and umbrellas. The pool deck is paved and includes both shaded and sunlit seating options, with greenery providing a natural backdrop.

Home in Jamaica

Ski and tennis house by Stratton Ski Resort.

BillyRating, 5 stars2 months ago

We spent our winter break at Adam's condo. This condo experience had all the important Cs: Clean Condo - it was very clean upon arrival. Convenient Condo - the Stratton shuttle stops right outside the door. Communicative Condo Owner - any questions we had were answered in a timely manner. Cost effective Condo - great value Okay I went overboard with the Cs but honestly it was such a great experience. Adam is great host and the condo worked out perfect for us! Hopefully we get a chance to stay here again!

4.95 out of 5 average rating, 22 reviews

An aerial view captures a modern home surrounded by lush greenery. A tranquil in-ground pool is set within a landscaped area, complemented by a stone fire pit and a gazebo. The exterior features a variety of trees, enhancing the serene atmosphere.

Home in Dorset

Idyllic Dorset Home: Serene Escape w/amazing views

StacyRating, 5 stars2 months ago

My group of 9 had a wonderful stay here! The house was very spacious, clean, and modern and accurately represented in the posting. John was extremely responsive during our process and proactively checked in with us to ensure we were able to check-in to the property smoothly. We had a small issue with one of the stove top burners and when we reached out to John, he followed up immediately to resolve the issue. I highly recommend staying here!

4.82 out of 5 average rating, 117 reviews

An aerial view of the property captures a serene outdoor space featuring a rectangular pool surrounded by lounge chairs. Nearby, tennis courts are visible, set against a backdrop of green lawn and trees, providing an inviting area for leisure activities.

Home in Warren

Charming Sugarbush Standalone Condo

PerryRating, 5 stars1 month ago

Great location and lots of space. We were able to ski in/out (look for "Cliff's Road" sign when skiing back) fairly easily, which was nice. Would definitely stay here again. Thanks!

5 out of 5 average rating, 10 reviews

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

Private Farmhouse with in ground pool!

ChrisRating, 5 stars7 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!

4.91 out of 5 average rating, 89 reviews

A wood stove is positioned within a brick fireplace, showcasing a warm fire glimmering behind a glass front. The surrounding brick offers a rustic touch, while stockings hang above, adding a seasonal element to the cozy ambiance.

Home in Chittenden

Comfortable, relaxing large country home

EdwardRating, 5 stars2 months ago

Great spot for a week of skiing! Danielle was very helpful and communicative throughout

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Condo rentals with a pool

Top guest favorite

An indoor pool area features clear water reflecting the wood-beamed ceiling overhead. Large windows allow natural light to illuminate the space, highlighting the smooth concrete poolside. A few lounge chairs are visible along the edge, offering a place to relax.

Condo in Warren

4.97 out of 5 average rating, 128 reviews

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

PedroRating, 5 stars1 month ago

Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

4.91 out of 5 average rating, 127 reviews

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

KateRating, 5 stars1 week 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!

A cozy living room is depicted, featuring a fireplace framed by decorative plants. A sleek flat-screen TV stands adjacent to the fireplace. A modern coffee table with a plant enhances the space, complemented by soft lighting along the wall. Comfortable seating options are visible.

4.9 out of 5 average rating, 50 reviews

Killington Mnt Escape Ski/Golf/Bike/Hike/Pool

MichaelRating, 5 stars1 week ago

It was a pleasure staying at Shirley's place for our last trip to Killington this season. The place was nice and clean, the kitchen had everything we needed to cook our meals, and the amenities in the building were great!

4.83 out of 5 average rating, 23 reviews

A cozy bedroom features a queen bed with white and gray bedding. Pine wood walls create a natural ambiance. A window allows soft light to enter, and a black and white framed artwork is displayed above the headboard. Two dark bedside tables provide additional storage.

Condo in Warren

Renovated Condo(unit #10) 3 Miles from Mtn

JohnRating, 5 stars2 months ago

We had a great weekend getaway! Close to Sugarbush for skiing, surrounding towns and restaurants! Would highly recommend a stay here.

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.

4.84 out of 5 average rating, 174 reviews

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

BenRating, 5 stars3 weeks ago

This condo has a great location, and the unit itself is extremely pleasant. If you're going to Killington I highly recommend it

4.82 out of 5 average rating, 112 reviews

A swimming pool is framed by well-kept grass and trees, with lounge chairs positioned nearby. The area is enclosed by a black fence, offering a sense of privacy. The surrounding hills can be seen in the background, creating a peaceful outdoor setting.

Condo in Warren

Modest Mountain Dacha

JoanneRating, 5 stars2 months ago

Very comfortable stay - convenient to ski wither Sugarbush or Mad River. Philip sent specific instructions for turning the heat up on arrival. It took a little while to warm up, but individual thermostats in LR and BR worked nicely. Local recommendations for restaurants and such were spot on.

An aerial view captures the surrounding winter landscape, highlighting the ski trail marked in white leading through a snowy forest. The location of the condo is indicated with a black circle, providing context within the picturesque mountain backdrop.

4.71 out of 5 average rating, 24 reviews

Ski-Home Condo! Renovated 3BR

GabrielRating, 5 stars1 month ago

Jeff and Melissa’s place was the perfect getaway with shuttles to take you to and from the mountain and a trail to ski back to the house. Would definitely stay here again!