Vacation rentals with a pool in Windsor County

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Top-rated rentals with a pool in Windsor County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Killington

4.92 out of 5 average rating, 165 reviews

Cozy Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Jun 21 – 28

ﺩ.ﺇ707 per night

Guest favorite

Condo in Killington

4.9 out of 5 average rating, 119 reviews

Cozy & Convenient Ski Home Condo

Ski Home to Trail Creek Close to the mountain This updated 1-level, 1 bedroom, 1 bath, condo is walking distance to Snowshed Base where you can access skiing, biking and the "fun" center. Ski home to your door from Snowshed Slope trail. Steps to the amenities building that houses the pool, hot tub, sauna & exercise area. Wood-burning fireplace, free firewood, in-unit laundry. The view outside your living area is of bucolic woods and a small stream. Killington will not run the shuttle mid-week.

Aug 30 – Sep 6

ﺩ.ﺇ639 per night

Superhost

Condo in Killington

4.85 out of 5 average rating, 242 reviews

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

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

May 30 – Jun 6

ﺩ.ﺇ417 per night

Guest favorite

Townhouse in Killington

4.93 out of 5 average rating, 232 reviews

Modern Mountain Condo with Spa, Pool, Sauna, Gym

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

Oct 30 – Nov 6

ﺩ.ﺇ1,939 per night

Guest favorite

Condo in Killington

4.94 out of 5 average rating, 175 reviews

Walk or Shuttle to Lifts/2BR @ Mt. Green Resort

Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

Aug 14 – 21

ﺩ.ﺇ545 per night

Guest favorite

Condo in Killington

4.96 out of 5 average rating, 103 reviews

CozyCub Pets, AC, Bike to Mtn, Fireplace, Walk out

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

Oct 22 – 29

ﺩ.ﺇ757 per night

Guest favorite

Condo in Killington

4.93 out of 5 average rating, 182 reviews

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain. check VRBO.1532508 mention this for a better deal

Oct 17 – 24

ﺩ.ﺇ602 per night

Guest favorite

Home in Plainfield

4.89 out of 5 average rating, 119 reviews

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool opens around May 2024! It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything just ask

Nov 5 – 12

ﺩ.ﺇ2,365 per night

Guest favorite

Apartment in Clarendon

4.92 out of 5 average rating, 133 reviews

Vermont Horse Farm

Enjoy a morning cup of coffee on the patio overlooking the horse pastures or an evening by a fire under the gazebo with a fire pit on this idyllic Vermont horse farm with glorious views. Close to many activities, such as hiking, skiing and swimming. Scenic retreat on a family owned and working farm. Here we have horses, donkey, chickens, goats, and of course our dogs and cats. There is a short hiking trail with beautiful views and a picnic table by the stream.

Jan 8 – 15

ﺩ.ﺇ368 per night

Guest favorite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

PRIME BASE AREA LOCATION THE HOME → King Beautyrest mattress → Coffee/Tea/Cocoa Bar → Nintendo Wii + Games → Fully Equipped & Stainless Kitchen → Fast Wifi SKI IN / SHUTTLE OUT (2022: Winter Only; Weekends only) → Shuttle to Snowshed/K1 → Ski home on a gorgeous quiet ski home trail OFF SEASON → World Class hiking & biking on Killington Mountain OFF THE MOUNTAIN → Breweries → Antique Malls → Golf Courses → Quechee Gorge → Disk Golf → Llamas Petting

Sep 29 – Oct 6

ﺩ.ﺇ649 per night

Guest favorite

Condo in Killington

4.87 out of 5 average rating, 149 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

May 21 – 28

ﺩ.ﺇ508 per night

Guest favorite

Condo in Killington

4.93 out of 5 average rating, 138 reviews

Renovated unit, prime location! Shuttle on/Ski off

We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

Oct 12 – 19

ﺩ.ﺇ621 per night