Vacation rentals with a pool in Chittenden County

Three modern condo units are visible, each featuring large windows and sloped roofs. Snow blankets the ground and rooftops, while wooden walkways lead up to the entrances. Surrounding trees create a natural backdrop, enhancing the feeling of seclusion.

4.94 out of 5 average rating, 31 reviews

Family & Couples Valley Getaway

RonaldRating, 5 stars1 month ago

This was a really nice condo for our family ski trip to Sugarbush. Really great and very well equipped especially the kitchen. The road in is a little difficult and its not just snow/ice but in the afternoon got very muddy and rutted. We were fine with a RAV4 and PriusAWD neither with snow tires. Will definitely look to rent again if available for our next trip. Thanks!

Superhost

A modern interior features a spacious living area with comfortable seating and a dining table. A well-equipped kitchen is visible, alongside a cozy sleeping area. Large windows allow natural light to brighten the space, with neutral tones creating a welcoming ambiance.

Camper/RV in Colchester

4.91 out of 5 average rating, 34 reviews

RV Camping by the Lake in Colchester, Vermont!

KaylaRating, 5 stars6 months ago

We loved our stay at William’s place! It was the perfect weekend for a doing a little glamping, and this spot offered everything we needed: a fire-pit, a cozy camper, and a great location. You’re within walking distance to the beach at Mallett’s Bay and a short drive away from downtown Burlington. The campground itself was a little packed when we stayed, but most folks kept to themselves. Other than that, great experience!

4.93 out of 5 average rating, 191 reviews

A warm living area is highlighted by natural wood paneling and a cozy woodstove. A coffee table is set with fresh fruit and drinks. A softly lit lamp beside a comfortable chair adds to the inviting atmosphere, while a door leads to a bedroom.

Cabin in Jeffersonville

Cozy two-bedroom cabin near Smugglers Notch

KrisRating, 5 stars12 months ago

We could not have asked for a better place for our eclipse adventure. The two bedroom cabin was spotlessly clean, well-appointed, cute and plenty of space for the 4 of us. We loved being out in the woods and enjoyed our walks around the pond enormously. Easy to get to restaurants and other activities, but away from the hustle and bustle. The staff were super friendly and very helpful. Not a thing to complain about, and would definitely recommend to anyone!

An outdoor pool area is surrounded by wooden decking, showcasing lounge chairs arranged neatly on either side. The inviting pool features clear water, with a simple building visible in the background amidst lush green trees.

4.97 out of 5 average rating, 29 reviews

Ski, Hike & Bike Basecamp Condo

NickRating, 5 stars2 months ago

We noticed this listing at first mostly due to its location. The condo is close to multiple Mad River Valley ski locations and it is near friends of ours that live locally in Vermont. Once we got there however, we realized that the condo is perfect for our family of four. The place was super clean and comfortable and gave us a nice place to eat/sleep before heading out for the day. The hosts were super responsive and proactive communicating rules and instructions for use of the place. Would highly recommend and would certainly consider staying again.

5 out of 5 average rating, 6 reviews

A waterfront property is showcased with a spacious deck featuring seating and a hot tub. The private beach area is visible alongside the sandy shoreline. Nearby, a grassy area is bordered by trees, enhancing the natural setting. Multiple homes can be seen along the shoreline.

Home in Colchester

Lakeside Bungalow ~ Pool | Hot Tub | Beach

ChelseaRating, 5 stars6 months ago

Kylie’s home was thoughtfully decorated and cozy. The lake views were really stunning - too cold to jump in but the jacuzzi was perfect. She was always available to message before and during my stay and asked for direct feedback towards the end of my trip in case there was anything that needed improvement. It was a great experience!

5 out of 5 average rating, 31 reviews

Home in Waitsfield

Winter Wonderful Waitsfield Spacious VT Home w/Spa

SeanRating, 5 stars6 months ago

Our stay in Sara and Mikes home in Waitsfield was incredible! Upon arrival into the mad river valley, the surrounding views were instantly beautiful and calming. The moment we stepped in the house we honestly felt right at home. The layout of the house is so calming and tasteful. Everything is perfectly organized, down to the labeling for all of the dishes and cookware so you’ll never have trouble finding what you need! Waking up and heading by downstairs for a workout in the home gym, followed by a dip in the hot tub on the secluded back deck was an insanely relaxing way to start the day. The custom built bed frames/furniture and the overall craftsmanship of the space added a comforting artistic value to the stay. Don’t get me started on the screen porch! This house is full of amenities and I’ve honestly never felt more at home at an air b&b stay. Nice quiet respectful neighborhood in an amazing community, would recommend this spot to anyone and we hope to return in the future!

4.99 out of 5 average rating, 119 reviews

A refreshing inground pool reflects the clear sky, bordered by a stone patio. The backyard features vibrant gardens alongside a two-story home with a combination of light gray and red siding. A deck area can be seen on the left side of the house.

Apartment in Monkton

Spacious Private Apartment w/ Green Mountain Views

Wai LingRating, 5 stars5 months ago

Amy’s place offered us a wonderful, relaxing stay at Monkton, with its stunning view of the mountains and peaceful surroundings. The clean, nicely furnished apartment was lovely and cozy. Amy was a great host. She was warm, welcoming, and very accommodating. Thank You Amy for the delicious apple cake chunks.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Popular amenities for Chittenden County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 12 reviews

An outdoor pool is visible in the foreground, surrounded by a deck and lush green landscape. Rolling hills and trees create a scenic backdrop, with mountains faintly visible in the distance under a clear blue sky.

Home in Essex Junction

Mansfield Manor at Essex

SarahRating, 5 stars6 months ago

Matthew’s place was perfect for our family trip. Clean, well-stocked , and comfortable. Plenty of space to spread out and so many thoughtful touches. Truly felt like home while we were there. The sunrises are gorgeous!

4.91 out of 5 average rating, 44 reviews

The exterior of a rustic farmhouse is showcased, featuring a welcoming porch and surrounded by vibrant greenery. A stone path leads to the entrance, where a blend of trees and shrubs complements the natural setting.

Home in Cambridge

4-bedroom Vermont Farmhouse close to Smuggs'

RachelRating, 5 stars9 months ago

We had such a lovely stay at the Pond House! Absolutely gorgeous property, beautiful home & furnishings, perfect for 2 families to stay comfortably. It was so peaceful out there, yet very convenient to activities. Already looking at future dates we could come back!

5 out of 5 average rating, 9 reviews

The living area is defined by a stone accent wall and features a modern media console containing a large flat-screen TV. A comfortable sofa is situated nearby, complemented by a cozy throw blanket draped over a wooden chair.

Home in Cambridge

Cozy Smuggs Townhouse Getaway

ColllnRating, 5 stars3 months ago

Owing to the winter closure of the pass on 108, we had a challenge with Google’s directions. Once we found the resort it was all systems go, great arrival directions, easy entry and comfortable home. The access to all of the amenities of Smugglers Notch was awesome. Both Stacey’s and DJ’s responses to questions were above and beyond. Totally great week! Thanks guys.

A cozy living area features two yellow armchairs and a tan leather sofa, complemented by a small wooden coffee table. Natural light floods in through multiple windows adorned with blinds. The textured wooden wall adds warmth to the space, enhancing its inviting feel.

Home in Underhill

4.92 out of 5 average rating, 12 reviews

Cozy Vermont Getaway between Smugs and Stowe

MichaelRating, 5 stars2 months ago

We stayed here as a base for skiing Jay Peak, Titus, Middlebury Snowbowl, Bolton Valley, and Trapp Family Lodge (cross country). Snowshoed for hours on our 2 "off days". Very convenient, and very comfortable. Felt right at home. Would definitely like to book same week next year!

4.97 out of 5 average rating, 32 reviews

Home in South Hero

Mott House, South Hero Vermont

ScottRating, 5 stars6 months ago

Our stay was very nice! Our top requests are clean, quiet and comfortable beds. All three were met. Pat, was very friendly and helpful with our stay. I would stay there again!

5 out of 5 average rating, 16 reviews

A swimming pool features clear water, surrounded by a sleek stone deck. Mountain views are visible in the background, with trees lining the area. The sky is overcast, adding a tranquil ambiance to the outdoor space.

Home in Lincoln

Vermont Guest House: Family-Friendly, EV, Dogs

BrunoRating, 5 stars2 months ago

Carin & Luke are incredible hosts! We felt so lucky to have found their place, it’s absolutely gorgeous, private, and spotless. It was the perfect balance of adventure and relaxation for our yearly ski trip to Vermont. The location is ideal: close to everything yet secluded enough to enjoy privacy and a true sense of tranquility. The home is exactly as pictured and offers fantastic value. Whether you’re looking for a family getaway or a cozy retreat, I can’t recommend it enough!

4.93 out of 5 average rating, 58 reviews

Home in Waitsfield

Winter in Spacious Waitsfield Home w/Spa & Loft

NicholasRating, 5 stars7 months ago

The house was just beautiful and the setting was quiet and peaceful, yet close to everything. The gym was just what we needed, the kitchen was outfitted with more than the essentials, and the screened in porch was a haven for morning book reading. Everything was clean and welcoming upon arrival. Thank you very much!!

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Condo rentals with a pool

A large outdoor pool is surrounded by a white picket fence, with snow covering the ground. The building beside the pool features multiple windows, and a clear blue sky is visible overhead, indicating a bright day.

Condo in Cambridge

5 out of 5 average rating, 4 reviews

Smugglers Notch Vermont/ 2 bedroom deluxe

DeniseRating, 5 stars10 months ago

Everything was great . We enjoyed our stay. Accommodations were very comfortable. Lots of things to do in the area. We will stay there again 😊. Love northern Vermont.

4.93 out of 5 average rating, 45 reviews

The exterior of a two-story condo building is presented, featuring gray wooden siding and large windows. Colorful flowers and lush greenery are visible in the foreground, with a ramp leading to the entrance. A lamppost stands nearby, adding to the welcoming outdoor space.

Condo in Bolton Valley

2-bedroom Condo at Bolton Valley

DanRating, 5 stars1 month ago

Loree was really great and responsive! She seems to really care! If we had one negative about the place it’s that you can hear the neighbors pretty well. Particularly when they leave their unit early in the AM. Otherwise, four of us spent a week there quite comfortably.

A seasonal outdoor pool is surrounded by a spacious patio area, with lounge chairs positioned nearby for relaxation. Lush greenery and distant mountains create a serene backdrop, enhancing the tranquil environment. Umbrellas provide shaded seating options, ideal for enjoying the natural scenery.

4.74 out of 5 average rating, 19 reviews

Lovely riverfront condo near MRG/Sugarbush

NickRating, 5 stars13 months ago

Great condo in a great location. Condo was well stocked with everything you need. Holly was veey quick and detailed in communicating.

A vibrant outdoor pool area is depicted, featuring round floating platforms in the water. Children can be seen playing, with sun loungers and green umbrellas arranged around the pool's edge. Lush trees provide a natural backdrop, contributing to a lively atmosphere.

Condo in Cambridge

5 out of 5 average rating, 12 reviews

1BR Smugglers Notch VT

IrinaRating, 5 stars12 months ago

Book was very quick to respond to all of our questions, the resort is nice and there are lots of things to do. Was a bit pricy due to the eclipse but overall we are happy with the stay

Superhost

4.1 out of 5 average rating, 10 reviews

Mountain Magic: The Cozy Oasis

KristenRating, 5 stars6 months ago

Perfect place for a fall getaway. The home is very comfortable and well taken care of. We would love to come back again.

A spacious living area features comfortable seating arrangements, including a light-colored leather sofa and a recliner. A wooden coffee table sits in the center. A mounted television is visible above a slate stone fireplace, with large windows allowing natural light and outdoor views.