Vacation rentals with a pool in Chittenden County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Chittenden County rentals with a pool

House rentals with a pool

Guest favorite
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
4.92 out of 5 average rating, 12 reviews

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!
Guest favorite
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
4.91 out of 5 average rating, 44 reviews

4-bedroom Vermont Farmhouse close to Smuggs'

RachelRating, 5 stars8 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!
Guest favorite
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
5 out of 5 average rating, 9 reviews

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!
Guest favorite
Home in South Hero
4.97 out of 5 average rating, 32 reviews

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!
Top guest favorite
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
5 out of 5 average rating, 16 reviews

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!
Guest favorite
Home in Waitsfield
4.93 out of 5 average rating, 58 reviews

Winter in Spacious Waitsfield Home w/Spa & Loft

NicholasRating, 5 stars6 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!!

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.
Top guest favorite
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
4.93 out of 5 average rating, 45 reviews

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.
Condo in Waitsfield
4.74 out of 5 average rating, 19 reviews

Lovely riverfront condo near MRG/Sugarbush

NickRating, 5 stars12 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
Condo in Waitsfield
4.1 out of 5 average rating, 10 reviews

Mountain Magic: The Cozy Oasis

KristenRating, 5 stars5 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.
Condo in Waitsfield
4.75 out of 5 average rating, 24 reviews

Battleground 41 * Perfect VT Getaway near MRG

JamesRating, 5 stars1 month ago
We came back! Hosted our annual high school friends ski trip again in this great Battleground condo. It's perfect for a MRV ski trip; easily accessible to Sugarbush, Mad River Glen, and town and its restaurants alike. Very comfortable space, beautiful surroundings with the river out back, and the sauna after a ski day is an added, rejuvenating plus. We'll gladly come back again!
Superhost
A spacious living area features a large red sectional sofa positioned near two windows, offering mountain views. A small wooden coffee table with a chess set sits on a patterned rug. A floor lamp and side tables add functional touches to the room.
Condo in Richmond
4.76 out of 5 average rating, 92 reviews

Family friendly slope side condo w/ free parking.

JakobRating, 5 stars1 month ago
Great place, well equipped kitchen, and amazing location for skiing Bolton Valley. Hosts were clear and responded quickly.

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