Holiday rentals with a pool in West Windsor

4.91 out of 5 average rating, 212 reviews

Home in Killington

Luxury 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!

4.93 out of 5 average rating, 107 reviews

Condo in Mendon

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

4.94 out of 5 average rating, 107 reviews

Home in Springfield

Ski Mountain View Estate

Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Pool is closed for winter

4.89 out of 5 average rating, 139 reviews

Home in Plainfield

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 will be reopened around May 2025 (weather dependent. 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 ask!

4.94 out of 5 average rating, 120 reviews

Treehouse in Stockbridge

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

4.8 out of 5 average rating, 188 reviews

Condo in Ludlow

Okemo Mountain Getaway for Families w/ Pool Access

Perched on Okemo mountain, this spacious condo is the perfect year-round escape for families and groups. With ski-in/ski-out access, a cozy wood-burning fireplace, and a private balcony, it's perfect for any season—whether you're carving the slopes, hiking scenic trails, or enjoying the vibrant fall colors. Take a dip in the seasonal shared pool or unwind in the hot tub. Featuring a fully equipped kitchen, BBQ grill, and all the comforts of home, it's the ideal mountain getaway!

4.91 out of 5 average rating, 174 reviews

Renovated 1BR, Walk to Lifts, Covered parking

Our comfortable 1-bedroom condo in Building 3 of the Mountain Green Resort provides a bright yet cozy home base for your Killington getaway. Our condo features a new kitchen, dedicated Wi-Fi, and smart TVs. Conveniently located within walking distance to Snowshead, it's perfect for all your mountain activities. The shuttle runs daily through the winter season. The indoor pool, hot tub, and gym are open daily. The outdoor pool is open Memorial Day through mid-September.

4.97 out of 5 average rating, 152 reviews

Barn in Newfane

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $80 per trip per dog

4.96 out of 5 average rating, 131 reviews

Dog-Friendly Mtn Escape/AC/Pool/

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy electric fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

4.94 out of 5 average rating, 171 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.

4.89 out of 5 average rating, 130 reviews

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

Our cozy two-bedroom condo is just steps from the lifts, spa, ski shops, and restaurants, with a three-minute drive to Killington. Nestled in the Green Mountains, you’ll have access to skiing, hiking, world-class golf, snow tubing, and scenic mountain views. The condo features seasonal amenities including a pool, fitness center, hot tub, sauna, steam room, and more — perfect for both adventure and relaxation!

4.99 out of 5 average rating, 113 reviews

Cozy Condo next to Resort * AC and Pool *

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! King bed and Queen pullout sofa sleeps up to four (4). This property is Shuttle In/Out (Sat & Sun and holiday periods Dec - April). Killington Reg #004858

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House rentals with a pool

4.89 out of 5 average rating, 80 reviews

Home in Killington

Golf, Bike, Fish, or Hike!

SooRating, 5 stars2 months ago

Ashley was super friendly and responsive and her place was as described with everything I need and more to make me feel right at home. Would love to stay here again. Thank you so much for letting us stay at your beautiful place!

4.89 out of 5 average rating, 247 reviews

Home in Mendon

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month ago

We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!

4.92 out of 5 average rating, 26 reviews

Home in Grantham

Beautiful & Bright Eastman Home

NormaRating, 5 stars1 week ago

Beautiful and spacious home. Everything was clean and at any point I would message Denise she would respond right away. The area was beautiful as well. I would definitely book her home again.

4.93 out of 5 average rating, 211 reviews

Home in Keene

The Brick House on Washington Street

PaulRating, 5 stars1 week ago

Great stay and was exactly what we needed for our entire family for a weekend wedding!

5 out of 5 average rating, 26 reviews

Home in Hartford

The Fairway House - Premier Golf Course 3 BR Home

KarenRating, 5 stars3 months ago

Jenna' place was great! Nice open and comfy feel to the living room and dining room. The kitchen was well stocked and really clean. The beds were comfortable and the bedrooms were cozy. I would definitely recommend Jenna's home.

5 out of 5 average rating, 17 reviews

Home in New London

“Big Red” @ New London/Sunapee | Lake-Ski-Wellness

AdilaRating, 5 stars2 weeks ago

We thoroughly enjoyed our stay at the Big Red house in New London! The host, Chris, was so helpful in working with our dates. We traveled to New London for my mother-in-law's celebration of life, and I could not think of a better place to stay with my family and close family friends. The children (and adults!) enjoyed the game room and other amenities such as the screened porch and hot tub. We would have used the sauna/cold plunge if we had more time. The house was spacious, comfortable, and very private but easy access and close to downtown New London which was perfect for us. Again, I must highlight how gracious and helpful the host was - it was one of the best experiences I had so far with Airbnb. Please consider staying here - you will love it!

4.97 out of 5 average rating, 59 reviews

Home in Woodstock

Dana Road House Sunlit VT Country Home w/HotTub

EstherRating, 5 stars6 months ago

Kat’s house on Dana road was the perfect place for our vacation to Vermont. Our family appreciated the clear instructions, helpful hints, and well thought out amenities. We really liked the Whisper Hill products in the bathrooms and made sure we went to the store in Quechee to buy some of the lotion before we left. We have stayed at a lot of AirBnB’s, but the house on Dana road was the most well equipped out of all of our stays!

4.91 out of 5 average rating, 89 reviews

Home in Chittenden

Comfortable, relaxing large country home

EdwardRating, 5 stars3 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

5 out of 5 average rating, 7 reviews

Condo in Ludlow

Mountain Vista 3-BR Haven at Jackson Gore Resort

MatthewRating, 5 stars4 months ago

Noah’s place on the mountain was amazing! Ski in and ski out was so convenient. The place was exactly as described and was beautiful. The beds were super comfortable and the house was extremely clean. The indoor parking was the best ! Noah was great through the whole communication process. I would definitely rent this place again and we plan to go back this year.! Absolutely a must stay if you’re going to Okemo!

4.59 out of 5 average rating, 100 reviews

NEW Killington Studio: Great Location! Comfy. 431

JohnRating, 5 stars4 months ago

Nice cheaper lodging on the access road

4.99 out of 5 average rating, 120 reviews

Condo in Dover

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars3 months ago

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

4.95 out of 5 average rating, 99 reviews

Condo in Ludlow

Winterplace - Steps away from Slopes

MichaelRating, 5 stars2 months ago

A short walk to the ski slopes. The host was very helpful and proactive recommending where to go to ski based on your skill level. The place is functional and spacious. my favorite two things was proximity to the ski lifts/slopes and very comfortable mattresses/beds. When I ski, I need a nice rest and this place is a great for that. I would recommend this place and I would stay at Andrew's place again. Thank you Andrew for a great vacation!

4.92 out of 5 average rating, 12 reviews

Beautifully renovated spacious 2 room 2 BA suite

StevenRating, 5 stars5 months ago

great place to stay Joanne was a great host and responded quickly if I need anything

4.89 out of 5 average rating, 162 reviews

Modern Killington Farmhouse Condo: Close to Resort

RodneyRating, 5 stars3 months ago

Great home near the mountain, exactly how described and shown in pictures. We had a wonderful stay.

4.78 out of 5 average rating, 308 reviews

Serene Top Floor Condo (resort style amenities)

NikitaRating, 5 stars3 weeks ago

Amazing view and cozy vibes. Hot tub and a pool are fun amenities to have. Building has freshly renovated pool and tubs. If you like it there are also sauna pods. So do not forget your swimsuit. It was clean and if you cook there is a kitchen. On top of that it was great to have a balcony with a view. May is a nice time to come even if you are not skiing because it’s not crowded and nature is stunning. And there are plenty of spots for mountain bike. Scott is a great host and local recommendations are helpful and honest. Visit liquid art, if you want a good cup of coffee that’s the right place. Great place!