Vacation rentals in Chittenden

4.81 out of 5 average rating, 133 reviews

Home in Tinmouth

Vermont Lakefront Getaway "The Wild Loon"

This home was built in 2020 with the beautiful lake and mountain views in mind. The Wild Loon is what we decided to name our retreat because we are often visited by wild loons here on the lake. The Wild Loon has an open concept floor plan. Sleeping arrangements are upstairs and downstairs in the basement. The half bath, kitchen, living and dining room are all on the main floor. Parking is directly across the road and can fit 4 vehicles in the summer, spring and fall 3 vehicles during winter

5 out of 5 average rating, 5 reviews

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

4.89 out of 5 average rating, 9 reviews

A grassy area features a fire pit surrounded by several white Adirondack chairs. A large tree provides shade beside the inviting white house, which has multiple windows and a porch. Scenic views of the landscape are visible in the background.

Home in Poultney

Snowberry Farm Home Sweet Home

This memorable place is anything but ordinary. Hike the hayfields on the mowed paths! Fish in the Pond and enjoy the peace and quiet of this comfortable and spacious home. Star gazing is on the menu too! One mile to rail trail for bike enthusiasts. This house is very welcoming & well equipped for entertaining family & friends. Room for everyone & extra space for quiet reading & conversation. Cider house, craft breweries, dining options& golf all nearby. Escape Florida or Arizona summer heat!

4.92 out of 5 average rating, 171 reviews

A cozy bedroom features a wooden bed with a light-colored comforter and decorative pillows. A subtle grey blanket is neatly rolled on the bed. A dresser and a TV are positioned against the wall, with a bedside lamp providing soft lighting, complemented by natural light from a nearby window.

Cottage in Fair Haven

Historic Cottage 2 Bedroom 2 Bath Fast Wifi

Ski season has begun! Picturesque cottage next to the Castleton River. You can wake up to the birds chirping and fall asleep to the frogs croaking. Hourly church bells ring throughout the day. Walk down the historic slate sidewalk to the park and local beer, pastries & the best diner! Minutes to many lakes, trails & mountain activities. Perfect for day trips to Killington, Okemo, Woodstock, Lake George, Vergennes, Rutland, Burlington & Saratoga Springs. Message us about seasonal discounts!

4.93 out of 5 average rating, 61 reviews

A modern walk-in shower is enclosed with glass doors, featuring a colorful tiled floor and ambient lighting along the ceiling. The showerhead and handheld sprayer are positioned on the wall, with corner shelves displaying various toiletries.

Vacation home in Rutland

very nice vacation rental 20 min from Killington

Very nice vacation rental 20min from Killington and Pico. 30min from Okemo. 20 minutes from Chittenden Reservoir. 20 minutes from Mount Tabor. 20 minutes from Lake Bomoseen. 15 minutes from Proctor. 10 minutes from Rutland Airport. Private code lock entrance to a full apartment with no shared spaces. Full kitchen, walk in shower, washer dryer, two bedrooms with three queen size beds and Roku TV. Pull out couch in living room plus additional cots. Right off rt 7 on two acres in Rutland.

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

4.97 out of 5 average rating, 30 reviews

An indoor jacuzzi room features ample natural light streaming through multiple windows. The room is surrounded by wooden paneling, enhancing the cozy ambiance. A spacious, circular jacuzzi is positioned in the center, complemented by a built-in bench along one wall.

Cabin in Killington

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

4.97 out of 5 average rating, 33 reviews

A modern kitchen features wood cabinetry and stainless steel appliances. A polished countertop provides ample workspace, while a multiple-burner stove and microwave cater to cooking needs. Natural light enhances the room through a nearby window, complemented by patterned curtains. A trash can and sink are also visible.

Apartment in Pittsford

Norm's Place

Located in historic Pittsford Vermont, come stay in our newly renovated private unit. Close to Killington and Pico for skiing, the Mountain Top Inn , The Brandon Inn and Lilac Inn for weddings and events. Walking distance to the Pittsford Recreation center and walking trails. Convenient to swimming at the Chittenden reservoir or State Parks. Lots of opportunities for hiking and experiencing local breweries. Come see what our beautiful state has to offer!

4.96 out of 5 average rating, 26 reviews

The kitchen features a modern design with white cabinetry and a wooden countertop. Two windows allow natural light to brighten the space, while stainless steel appliances, including an oven, are positioned along the walls. A sink is centrally located, enhancing functionality.

Home in Cavendish

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

5 out of 5 average rating, 4 reviews

A charming red house is positioned among green trees with a well-maintained lawn. The porch features rockers, and a wooden fence lines the front. The exterior is complemented by a metal roof and traditional windows, inviting a warm atmosphere to the property.

Home in Pomfret

Next to Saskadena Ski, Great Views | Half Past Six

Welcome to your Vermont retreat! Nestled near the base of Saskadena Six Ski Hill, and conveniently located just a short drive to the historic town of Woodstock, this picturesque mountain-view home offers the ultimate getaway for families and friends alike. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet-Friendly, fee applies.

5 out of 5 average rating, 59 reviews

A spacious deck features four wooden Adirondack chairs arranged around a small table, inviting relaxation. The lush green backyard is visible, complemented by trees and an open area, enhancing the sense of privacy and tranquility in the natural surroundings.

Chalet in Mount Holly

Cozy chalet mins from Okemo & VAST.

Come enjoy some time in our cozy & relaxing 3-bedroom, 2-bath home. If you prefer a winter or summer getaway, all the options are available. Minutes from all activities and restaurants. Enjoy the nearby hiking and biking trails, Buttermilk Falls, Jackson Gore and Okemo SP. Property located opposite mountain traffic. Hang a left on 103 when leaving JG/ Okemo Main Rd.

4.92 out of 5 average rating, 25 reviews

Cottage in Shoreham

Breathtaking, waterfront rental on Lake Champlain

Our secluded spot in the quaint town of Shoreham, Vermont will be sure to feel relaxed, rejuvenated, and ready to book your next stay. With 3 newly renovated cottages, our guests feel at home from the moment they step onto the property. With outstanding views and breathtaking sunsets overlooking the Adirondack Mountains, we all can't get enough of Watch Point.

Vacation rentals for every style

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Popular amenities for Chittenden vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chittenden's top sights

Pico Mountain Ski Resort100 locals recommend

Deer Leap Trail40 locals recommend

Green Mountain National Golf Course35 locals recommend

Mountain Top Inn & Resort32 locals recommend

Clear River Tavern23 locals recommend

Gifford Woods State Park20 locals recommend

Other great vacation rentals in Chittenden

5 out of 5 average rating, 12 reviews

A wooden railing frames the outdoor balcony, offering views of the calm lake. Sunlight glimmers on the water's surface, with green hills visible in the background. A few boats are moored nearby, and the scene conveys a serene outdoor environment.

Home in Wells

Breathtaking Lakeside Retreat!

4.85 out of 5 average rating, 249 reviews

An inviting living area is highlighted by a stone fireplace, surrounded by wooden walls and a peaked ceiling. A cozy seating arrangement includes a leather couch and two footrests, while a small table holds a lamp. Windows offer glimpses of the outside ambiance.

Cabin in Mendon

THE CABIN....a Vermont log home

4.75 out of 5 average rating, 92 reviews

An outdoor pool is surrounded by lounge chairs and red umbrellas. Lush green trees frame the space, creating a serene environment. A small poolside shed is visible, adding functionality to the area.

Condo in Killington

Still 89 Trails Open, Low, Low Rates

4.84 out of 5 average rating, 88 reviews

The spacious living area features a stone fireplace flanked by comfortable seating arrangements. Large windows provide natural light, creating a warm atmosphere. A wooden mantle is adorned with decorative skis, while a coffee table complements the seating. Light fixtures add a soft glow to the room.

Home in Killington

Killington Racquetball House

4.96 out of 5 average rating, 53 reviews

The interior of a Scandinavian outdoor barrel sauna is visible, featuring wooden benches positioned along the walls. A small stove is located at the center, with a wooden bucket and ladle placed nearby. A large round window offers views of a green landscape and distant mountains.

Home in Chester

Farmhouse w/ views close to skiing sauna EV CHRGR

5 out of 5 average rating, 55 reviews

A newly built vacation home features a warm wooden exterior with large windows. It is surrounded by a snowy landscape, with a spacious front porch extending outwards. Stone landscaping borders the house, and trees are visible in the background, creating a peaceful winter scene.

Home in Chittenden

Gigi and Pops' Secret Cabin

5 out of 5 average rating, 8 reviews

A warm hot tub is presented against a snowy landscape, surrounded by trees bare of leaves. The distant view of the reservoir is framed by the serene white of winter, inviting relaxation and tranquility.

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington