
Vacation rentals with a pool in Chittenden County
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Top-rated rentals with a pool in Chittenden County
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Winter in Spacious Waitsfield Home w/Spa & Loft
Our ideal home for a memorable vacation in Waitsfield, Vermont. This location offers over 3,900 sq ft of well-appointed living space. Only 15 min from Sugarbush and Mad River Glen ski resorts and 1.4 miles from Waitsfield center. This house is perfectly situated for fun in every season. Equipped with a new and modern hot tub, fire pit, screened porch, gym, ping pong, so you'll never be bored! Plenty of room with space to sleep up to 8 guests comfortably in 3 spacious bedrooms. We love it here!

Private Suite in the Green Mountains
Relax in a country setting, centrally located to Vermont attractions. This private apartment in the trees boasts three beds and a full kitchen. With views of the Green Mountains, you will be a short drive away from quaint towns, skiing, breweries, hiking, and swimming. On the property, enjoy the fresh mountain air, changing leaves, and local flora and fauna. In summer, cool off after a hike or bike in the shared pool. In winter, you're 15 minutes to Mad River Glen and 30 to Sugarbush Ski Resort.

Family friendly slope side condo w/ free parking.
This ski-in/out trailside condo is located less than 30 miles from the best dining/shopping/hiking in Stowe, Burlington, Waterbury & Montpelier. It includes free parking & WiFi. Located next to the Mountain Market & James Moore Tavern, this gem is just a few steps away from swimming or skateboarding at the Sports Center, as well as 5 out of the 6 resort's ski lifts, including Wilderness which provides access to all natural backcountry alpine terrain & the Vista Quad's mountain bike trail system.

Mott House, South Hero Vermont
Apple Island Resort offers a variety of accommodations. The Lewis & Laura Mott House is rich in history & overlooks Apple Island Marina. The L&L Mott House is both the oldest & newest accommodation offered. Remodeled in 2018 with exquisite attention to detail, the historic house gives the architectural feel of an 1830s farmhouse while offering the latest in modern conveniences. Able to accommodate up to 8 guests, the L&L Mott House will provide an unparalleled home base for your special day.

North Burl - 1BR Loft with Private Porch
Private entrance 1 bedroom apartment in safe quiet burlington neighborhood. Master BR has 1 queen bed, closet, and work table. Living room has 1 twin daybed that pulls out to king size bed. Sofa, dining table, work table, TV and closet. Full kitchen including stovetop, oven, microwave, fridge, etc. 1 bathroom with shower. Large private porch with seating. (Hammock w/ stand available) Off-street parking for 2 cars, convenient to bus line, bike path, lake and river trails. Parks nearby.

Romantic one-bedroom cabin near Smugglers Notch
Our one-bedroom log cabins (we have several) have everything you need for a private, romantic getaway for two. With a king-sized bed, woodstove, two-person whirlpool tub, kitchen, bath, living room, TV, and free WiFi, these cabins have all the comforts of home and serve as a peaceful escape from everyday stress. This cabin has a maximum occupancy of 4 guests, with a sleeper sofa in the living area. Close to skiing/snowboarding, snowmobiling, hiking, horseback riding, wedding barns and more.

Cozy Little Mountain Condo
Relax on the mountain in our little condo. A cozy space to enjoy fresh mountain air. Enjoy easy access for ski in/out, hiking, mountain biking, leaf peeping…something to love here during every season! Bedroom with a queen bed. Pull out couch is best suited for children or one adult—two large adults may find it a tight fit. Located approximately half-way between Burlington and Stowe, about 30 minute drive to either/or. Or check out Waterbury (our favorite) about 15 minutes away!

Spacious Private Apartment w/ Green Mountain Views
Guests enjoy views of Camel's Hump & the Green Mountains and beautiful farmland to the East. This space is great for couples & solo adventurers. My home was built in 1810 & the Guest Studio was added onto the house in 1980. Conveniently located midway between Middlebury & Burlington, also a great home-base to take a day trip to the Stowe & the Mad River Valley. Much to explore- visit local farms & apple orchards, great hikes and Lake Champlain, breweries and wineries.

Slopeside Bolton Valley Studio
Bright and charming studio at Bolton Valley Resort. Ski, ride, snowshoe, bike, hike within seconds of leaving your front door. The studio is at 2000' elevation tucked into the valley with easy access to dozens of beautiful trails. You'll experience nature at its best! When you're finished playing outside come inside to your home away from home. It has a king size bed, full kitchen, TV, and bathtub. Ideal for couples and solo travelers. Not suitable for animals or children.

2-bedroom Condo at Bolton Valley
A spacious 2-bedroom condo for the entire family at Vermont's most family-friendly ski resort! This condo is located within Bolton Valley Resort, next to the sports center and a short walk to the ski lifts. Enjoy year-round adventures! Alpine, Nordic, and backcountry skiing, as well as mountain biking, hiking, swimming (indoors and out) and an indoor skate park. Enjoy all the mountain vistas--winter, spring, summer and fall--and find adventure around every bend!

Lakeside Bungalow ~ Pool | Hot Tub | Beach
Welcome to this Lakeside Retreat. This cozy waterfront property offers stunning lake views and access to a private beach. Enjoy a fully equipped kitchen, a spacious living area, and an outdoor deck for relaxing and watching the sunsets. Perfect for a family getaway or romantic escape. This property is a short drive to downtown Burlington for shopping and dining. Unwind in the hot tub, cool down in the pool or simply soak in the natural beauty of Malletts Bay!

Safe Quiet Lake Cabin Pvt-Beach HotTub Pool Path
⛱️ 🍺🍕🎣🏊♀️ Private beach guesthouse (beach 3 blocks away), hot tub ), heated swimming pool (open May-early September), walk to fishing, boating, dog friendly beaches, public tennis, volleyball, bocce ball courts bike paths picnic areas,& a diverse selection of top-rated restaurants and breweries. Relax and make the most of the amenities! Self check-in, safe parking, easy access to the Colchester Causeway and all of Burlington . A perfect getaway!
Popular amenities for Chittenden County rentals with a pool
House rentals with a pool

Mansfield Manor at Essex

4-bedroom Vermont Farmhouse close to Smuggs'

7-bedroom house close to Smugglers Notch

Winter Wonderful Waitsfield Spacious VT Home w/Spa

3BR lake home with hot tub, pool, & in-home gym

Vermont Guest House: Family-Friendly, EV, Dogs

Mountain View Modern Farmhouse

Sanctuary on the Brook
Condo rentals with a pool

Lovely riverfront condo near MRG/Sugarbush

Smuggler's Notch Vermont/ 1 bedroom Deluxe

Smugglers Notch 3 Bedroom

Ski, Hike & Bike Basecamp Condo

Wyndham Smugglers' Notch | 1BR/1BA King Bed Suite

1br Deluxe Unit -Nature Escape- Smugglers' Notch

Skier's Paradise Mad River/ Sugarbush

Smugglers Notch, Vermont - 1Bd Dlx
Other vacation rentals with a pool

Guest House on Otter Creek!

Cozy two-bedroom cabin near Smugglers Notch

Smuggler's Notch Resort in Vermont 1br suite, Sund

Smugglers Notch Resort 2 Bedroom

Modern Cabin near Burlington VT

Studio Cabin near Smugglers Notch

Mountainside Studio at Bolton Valley

Top Ski and Summer Resort Luxe
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- Rentals with pools United States
- Sugarbush Resort
- Jay Peak Resort
- Smugglers' Notch Resort
- Spruce Peak
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Burlington Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Val Caudalies - Vignoble & Cidrerie
- Vermont National Country Club
- Lincoln Peak Vineyard
- Domaine du Ridge
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Montview Vineyard