Vacation rentals with a pool in Windsor County

4.91 out of 5 average rating, 213 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

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

A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.

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, 108 reviews

An inviting pool with clear blue water is surrounded by a patio. Rolling green hills and a vast sky filled with white clouds create a scenic backdrop. A few lounge chairs and a dining area are positioned nearby, overlooking the tranquil landscape.

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

A refreshing outdoor pool is set within a landscaped area, featuring lounge chairs around its edge. The backdrop includes a contemporary building and rolling green hills, all under a clear blue sky with scattered clouds.

4.89 out of 5 average rating, 103 reviews

Updated large condo across from AT and skiing

Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.

4.89 out of 5 average rating, 139 reviews

A fenced outdoor pool area is surrounded by lush greenery and tall trees. The pool is heated and saltwater, reflecting the sunlight. Adjacent to the pool, a small shaded structure provides additional space and amenities.

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, 121 reviews

The treehouse design features large windows and wooden siding, surrounded by lush greenery. An expansive deck is equipped with comfortable seating and a fire table, providing a serene outdoor space for relaxation.

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.

A spacious outdoor saltwater pool is framed by comfortable lounge chairs and red umbrellas, providing shade. The surrounding area features lush greenery, enhancing the relaxing atmosphere. A shaded gazebo with seating is visible, inviting guests to unwind beside the pool.

4.95 out of 5 average rating, 115 reviews

Updated Dog-Friendly/AC/Across From Mountain/Pool

Experience comfort and convenience in this renovated 1BR/1BA condo in Mountain Green building #3. Dog-friendly and ideally located across from Snowshed and Ramshead lodges, it offers easy access to year-round activities. The condo features an open floor plan with a spacious living area, a fully updated kitchen, and modern finishes throughout. A free shuttle service stops at the building in winter. With all the amenities you need, this stylish retreat is the perfect getaway for all seasons!

An outdoor swimming pool is presented, featuring clear blue water surrounded by a concrete deck. Poolside seating is visible, along with lush greenery and well-maintained flower beds nearby. A tennis court is seen in the background, adding to the recreational appeal of the area.

4.94 out of 5 average rating, 161 reviews

CozyCub - Pool, Hiking, Mountain Biking

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.

4.8 out of 5 average rating, 188 reviews

A spacious living area features light green walls and vaulted ceilings, highlighted by a large arched window. A comfortable gray sofa is paired with wooden armchairs and a coffee table. A wooden dining table is visible in the foreground, and a cozy fireplace is fitted into the wall.

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!

4.97 out of 5 average rating, 147 reviews

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

3 bedroom townhouse with 2 full baths. Third bedroom is an open loft with 2 twin beds. The Woods is a luxury condo development located 3 miles from the lifts at Killington. Pool, gym and spa facilities. New: Killington Cafe & Wine Bar at the The Woods! 6 guests max per law. ONE well-behaved DOG upon approval (NOT 2 DOGS); $90 pet fee per stay. *INCLUDE YOUR PET AS A GUEST AND TELL ME ABOUT YOUR DOG WHEN BOOKING. Sorry, NO CATS. Summer guests, NO A/C in the unit.

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

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.

An aerial view showcases the condo complex surrounded by lush greenery, featuring multiple buildings arranged along a gravel path. An outdoor pool and a tennis court are visible, with sunlight reflecting off the water. Parking spaces are available nearby for convenience.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Villas

Luxurious estates for the ultimate escape

Popular amenities for Windsor County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 80 reviews

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

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!

4.94 out of 5 average rating, 33 reviews

The pool area offers a clear view of the surrounding greenery, with a modern home visible in the background. Lush trees and hills frame the scene, creating a serene environment. The water is calm and inviting, reflecting the bright blue sky.

Home in Ludlow

Hilltop 9-BR Mountain Retreat 5-min to Okemo

NicoleRating, 5 stars4 months ago

Great communication, even with two days of snow excellent clearance. Definitely recommend 4WD as noted in the listing. Otherwise great place/location for large family gathering! GO BIRDS!

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.

4.97 out of 5 average rating, 59 reviews

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

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!

Top guest favorite

A spacious living area features a comfortable gray sofa with blue accent pillows, positioned beside a wooden coffee table. Natural light floods the room through large windows, illuminating the hardwood floor. The open layout leads to a kitchen area visible in the background.

Home in Hartford

4.92 out of 5 average rating, 39 reviews

Bright & Modern Quechee Town House - Self Check-In

MariaRating, 5 stars1 week ago

We stayed at Michael’s place for 5 nights for our son’s graduation at Dartmouth. It’s a very comfortable house in a nice quiet location in cul-de-sac so there were no outside noises. The beds were comfortable, we slept well, there was enough room to spread out for everyone. We loved the proximity to Woodstock and Quchee gorge. And getting to Hanover to campus was an easy 20 minute drive. Michael is a great host! Very responsive and helpful. Thank you !

5 out of 5 average rating, 11 reviews

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

Private Farmhouse with in ground pool!

ChrisRating, 5 stars9 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!

4.95 out of 5 average rating, 19 reviews

A cozy living room features two white slipcovered sofas opposite a traditional brick fireplace, which is glowing with a warm fire. Natural light enters through several windows, complemented by minimalistic decor including a floor lamp and a woven basket.

Home in Hartford

Farmhouse, Fireplace & Office | Wheelock Hideaway

HeidiRating, 5 stars8 months ago

Very quiet and cozy. Comfortable beds. Lots of room for everyone.

4.91 out of 5 average rating, 89 reviews

An inground pool is featured in a fenced-in area, surrounded by greenery. A slide is attached to one side, and steps lead into the water. The pool deck provides ample space for lounging, with a view of the nearby trees and shrubs.

Home in Chittenden

Comfortable, relaxing large country home

EdwardRating, 5 stars4 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

4.98 out of 5 average rating, 53 reviews

Luxury Condo - with Garage Parking and Pool

MichaelRating, 5 stars3 months ago

Clean and updated condo. Great location. Short walk to snowshed and ramshead lifts.

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.

4.85 out of 5 average rating, 265 reviews

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

MichaelRating, 5 stars3 months ago

Apartment was clean including the bathroom, just as described by the listing. The place was very comfortable to stay at.

An outdoor pool is framed by a secure white fence, surrounded by greenery and lounge chairs. Sunlight reflects off the clear water, while soft clouds hover in the blue sky. A blue cover edges the pool, indicating preparation for use.

4.96 out of 5 average rating, 80 reviews

Bright & Cozy condo with AC, Tennis, and Pool

JodiRating, 5 stars1 month ago

very happy with our stay. Perfect accommodations. Everything was clean and sanitary. The host was communicative and friendly. We needed a hiking suggestion and he was great. Very personable through email. We will contact him again to stay there next year.

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.

4.93 out of 5 average rating, 80 reviews

Bike Golf hike pool Tennis 2 Bedrm at Mtn & Apres

BrianRating, 5 stars3 months ago

Looks exactly like the photos. It is close to the ski slopes, and spacious for a group of three.

4.95 out of 5 average rating, 99 reviews

An indoor pool area is illuminated by natural light streaming through large windows and skylights. The pool's surface reflects the blue and white tones of the decor, enhancing the spacious feel of the room. Elegant wall sconces add soft lighting to the atmosphere.

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!

A spacious bedroom showcases a king bed with balanced bedding, complemented by a flat-screen TV on a light-colored dresser. Natural light pours through the window, which is adorned with soft blinds, creating a bright atmosphere.

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

4.93 out of 5 average rating, 110 reviews

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

One Bedroom Suite Near Okemo

ChristopherRating, 5 stars2 months ago

Excellent apartment in a resort hotel. Well staffed and the property is kept in excellent condition. Highly recommend this host.

An outdoor pool area is showcased with a well-maintained pool surrounded by a paved deck. Sun loungers are placed at various points, accompanied by red umbrellas for shade. The backdrop features a multi-story building, enhancing the serene atmosphere of the space.