Holiday rentals with a pool in Chittenden County

Guest suite in Starksboro

4.94 out of 5 average rating, 83 reviews

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.

4.73 out of 5 average rating, 94 reviews

Condo in Richmond

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.

4.97 out of 5 average rating, 35 reviews

Home in South Hero

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.

4.97 out of 5 average rating, 195 reviews

Cabin in Cambridge

Studio Cabin near Smugglers Notch

Our studio log cabins (we have several) are cozy and quaint, making them the perfect choice for the couple looking for a private getaway or for the lone traveler looking to disconnect from the hustle and bustle of everyday life. This cabin has a max occupancy of two guests. Equipped with a queen-sized bed, gas log stove, kitchen, bath, couch, TV, and free WiFi, a studio cabin provides our guests with a safe space to relax and unwind. Close to all spring, summer, fall, and winter activities.

4.95 out of 5 average rating, 79 reviews

Chalet in Bolton Valley

Swanky Mountain Chalet 30 min.s from Burlington

Beautiful mountain chalet just steps away from Bolton Valley Resort and Mountain Bike Park in Bolton, Vermont. Best backcountry access in the state for hiking and a new Gravity Logic mt bike park! All the amenities, two private bedrooms with 2 full baths, amazing spot on the ski (and bike) trails, and just 30 minutes from Burlington and the airport. Sports center with indoor tennis and pickleball, indoor and outdoor pools, hot tub, sauna within walking distance, and great food and bars.

4.97 out of 5 average rating, 29 reviews

Ski, Hike & Bike Basecamp Condo

Relax with the whole family at this peaceful condo tucked into the trees with easy access to all that the Mad River Valley has to offer. It is a 10 min drive to just about everything: Sugarbush, Mad River Glen, Blueberry Lake, mountain biking, leaf peeping, waterfalls, swimming, fishing, and great eats! Plus some hiking, snowshoe and mountain bike trials right outside the door. Depending on the season, snuggle up by the stove, try out the sauna, play tennis or relax by the pool.

4.98 out of 5 average rating, 120 reviews

Apartment in Monkton

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.

Apartment in Bolton Valley

4.93 out of 5 average rating, 153 reviews

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.

4.81 out of 5 average rating, 32 reviews

Tiny home in Ferrisburgh

Dog-Friendly Secluded Cabin

Small cabin on our 24 acre country site. One charming room with a connecting dressing room and full bath. Fresh water pond for swimming plus a clay tennis court. Dogs are welcome due to the fencing we have installed around the small meadow that surrounds the cabin. A limit of two dogs per visit. AVAILABLE FROM MAY 15th TO OCTOBER 15TH. We also have a private king-bedded suite off the main house which rents for $150/night. A small child could sleep on the futon couch.

4.93 out of 5 average rating, 45 reviews

Condo in Bolton Valley

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!

5 out of 5 average rating, 11 reviews

Home in Colchester

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!

4.88 out of 5 average rating, 678 reviews

Apartment in Burlington

Lake Cabin Pvt-Beach, Hot Tub Walk-Dine Breweries!

⛱️ 🍺🍕🎣🏊‍♀️ 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!

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Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Popular amenities for Chittenden County rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.91 out of 5 average rating, 45 reviews

4-bedroom Vermont Farmhouse close to Smuggs'

DeborahRating, 5 stars4 months ago

Great house! Clean, character -filled, and well equipped for our group of 4 couples. Beautiful location—secluded yet so close to Smuggs.

5 out of 5 average rating, 20 reviews

Home in Richmond

Sunset Treehouse

JustinRating, 5 stars3 months ago

If you’re looking to ski at Bolton Valley, really tough to beat this location unless you’re right in the resort. Worked out very conveniently for our family of 4 (2 adults and 2 young kids). Cleanliness is important to us and the bathroom, kitchen, foyer, etc. we’re all in great shape and updated. King size bed was comfortable. Some of the bedroom furniture was a bit dated, but was livable given the rest of the nice amenities and overall cleanliness of the apt….and the location to the lifts… Lucas was very upfront about the fact that we would need to bring an air mattress of some sort for the kids. This worked out more than fine as we sat up the mattress in the living room. All in all, this apt would work out well for anyone wanting close proximity to the ski lifts…

4.88 out of 5 average rating, 26 reviews

7-bedroom house close to Smugglers Notch

LetitiaRating, 5 stars22 months ago

Spent the weekend for our son’s wedding at Boyden Farms. We were a group of 11 with plenty of space! Multiple bathrooms and 2 kitchens were a big bonus! Clean, well-stocked, spacious, great view of mountain and nice walking trails. Staff is responsive and friendly. A great weekend was had by all! Thank you!!!

5 out of 5 average rating, 16 reviews

Home in Lincoln

Vermont Guest House: Family-Friendly, EV, Dogs

BrunoRating, 5 stars4 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, 59 reviews

Home in Waitsfield

Winter in Spacious Waitsfield Home w/Spa & Loft

SubhajitRating, 5 stars1 week ago

We had a great stay in this house. It is really spectacular! Everything is really well maintained and we like the kitchen fully stocked. There are so many amenities in this house- you will never feel bored…very clean house and highly recommended!

MariamRating, 5 stars24 months ago

*Smugglers Ski Resort* 2BR sleeps 8

Will come back here again , and again

Home in Colchester

4.58 out of 5 average rating, 12 reviews

4BR Lakefront | Pool | Fireplace | Deck

AndrewRating, 5 stars14 months ago

We were in town for a hockey tournament and five people were staying here. There was plenty of room for all five us comfortably. Everyone had their own bedroom (three single people and one couple). There was a great view of the lake outside the front of the house. Everything from the doors to the light switches, refrigerator, and everything in between was labeled so you knew exactly how something worked (which was a huge plus...it took the guess work out of things). We definitely would stay again if in town.

Ski at Smugglers* 4BR Sleeps 12* Full Condo

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Condo rentals with a pool

4.74 out of 5 average rating, 19 reviews

Lovely riverfront condo near MRG/Sugarbush

NickRating, 5 stars15 months ago

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

4.92 out of 5 average rating, 37 reviews

Condo in Richmond

Family condo ski in/ski out Bolton main lodge!

StephenRating, 5 stars3 months ago

Great view of the mountains across from the trails! Beautiful sunset from the balcony. Jetted bathtubs were appreciated too!

Condo in Cambridge

4.81 out of 5 average rating, 16 reviews

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

SamRating, 5 stars10 months ago

Easy check in, clean place! Really enjoyed our stay! Have a great shuttle service around the resort if needed.

4.5 out of 5 average rating, 4 reviews

4 bedroom slopeside at Sugarbush Mount Ellen!

JimmieRating, 5 stars4 months ago

Fun, unique location in former Hotel with shared amenities in the common area like game room with shuffleboard and table tennis, hot tub, and sauna. Mike was very responsive and understanding after an invited guest from our party disturbed the other condo owners in this building. The result was a fair and understanding handling of the situation.

4.1 out of 5 average rating, 10 reviews

Mountain Magic: The Cozy Oasis

KristenRating, 5 stars7 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.

4.67 out of 5 average rating, 12 reviews

Secluded condo with sauna, pool, & tennis courts

AndreRating, 5 stars5 months ago

Beautiful secluded spot mere minutes from services and the slopes.