Vacation rentals in Chittenden

4.94 out of 5 average rating, 121 reviews

A sunroom showcases high wooden ceilings with skylights, enhancing natural light. A comfortable seating area, set with a light-colored couch and side table, is positioned next to large windows offering views of the outdoors. A dining table, accompanied by four chairs, occupies one corner of the space.

Home in Rutland

Mountain Getaway Pet friendly

Escape to our charming getaway, ideally located in Rutland just 20 minutes from the world-famous Killington Ski Resort! Whether you're here for skiing, snowboarding, hiking, or simply enjoying the serene beauty of Vermont, our home offers the perfect base for all your adventures. Our home offers a cozy and welcoming environment, perfect for families, couples, and groups of friends. You'll love the combination of comfort, convenience, and proximity to the best of Killington's outdoor adventures.

The exterior of a yellow cottage is showcased against a backdrop of colorful autumn foliage and rolling mountains. A manicured lawn leads to a fenced area, providing a peaceful setting for outdoor activities enhanced by the natural beauty surrounding the property.

4.88 out of 5 average rating, 34 reviews

MT Top Inn-6 Minute Walk-4+ BR-Pets OK & Grill-Ski

Walk to the Inn for weddings, or a short drive to Pico/Killington. Our 4 BR country cottage sleeps 9-10, with beautiful mountain views. Sit on the deck overlooking Blue Ridge Mountain, or enjoy the restaurant @ the Mountain Top Inn and Resort a short 6 minute walk. Nature walk, hike, mountain bike, or x-country ski out your back door, or swim or Kayak in the Chittenden Reservoir, downhill ski at Killington/Pico, or easily access the Green Mountain National Forest and Trails to the Long Trail.

4.98 out of 5 average rating, 170 reviews

Home in Mendon

New Firepit, Great Location, Dog Friendly, Kitchen

Welcome to @MendonMtGetaway - my warm & cozy VT retreat! With 3 bedrooms, comfy living room, full kitchen, washer/dryer, AND office space - I hope you'll feel at home right away. You are in a wonderful location here. Turn left & you are just minutes down the road from ski heaven - Killington and Pico Mountains! Turn right, and you're just minutes from cute & historic Rutland. Either way you’ll find tons of great outdoor activities & hiking, and lots of local shops and restaurants.

4.97 out of 5 average rating, 147 reviews

A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.

Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

An aerial view showcases a modern home nestled among trees, illuminated warmly at dusk. The exterior features dark wood siding and large windows, with a stone-lined driveway leading to the entrance. Surrounding natural foliage enhances a serene atmosphere.

4.95 out of 5 average rating, 43 reviews

Backyard Deck+Modern Interior | House on the Rocks

Welcome to "House on the Rocks" — the perfect place to bring your family on a unforgettable vacation. Nestled in Chittenden Vermont, we're the perfect stay for events near The Mountain Top resort and Killington Ski Area. And the ideal location for both outdoor activities or taking some time to relax and enjoy the tranquility with family. Enjoy a delightful stay in our modern 4 bedroom, 2.5 bath home. - Backyard deck w/ BBQ grill - Nice/Modern comfy interior - Prime location

A spacious living area features a cathedral ceiling adorned with wooden beams. Large floor-to-ceiling windows allow for abundant natural light and views of the surrounding forest. Comfortable seating arrangements include a dark sofa and matching armchairs, complemented by a wooden coffee table and decorative plants.

4.95 out of 5 average rating, 63 reviews

Private Vermont Retreat | Mt Top Inn & Killington

Secluded post-and-beam retreat on private acres in Vermont’s Green Mountain National Forest, minutes from Mountain Top Resort and 20–25 minutes to Killington and Pico. Light-filled home with soaring cathedral ceilings, floor-to-ceiling windows, and two south-facing decks with mountain views. Direct access to hiking, biking, snowshoeing, and cross-country ski trails. Ideal for year-round escapes, ski trips, wedding stays, and peaceful mountain getaways.

4.82 out of 5 average rating, 56 reviews

A living area features a rustic stone fireplace, with a cozy seating arrangement to one side. A wooden shelf displays books and decor. A television is positioned on a wooden cabinet, while logs are neatly stacked beside the fireplace, contributing to the warm atmosphere.

Cabin in Chittenden

House on Molly Brook Trail

We open our house for Airbnb guests at the end of May mid October. Our house is tucked in the Green Mountain Forest. A winding private road brings you up the hill to our house. We are two miles from the Chittenden reservoir which is great for swimming, fishing and kayaking. 30 minutes from Killington which offers a wide array of activities and restaurants. A place to truly get away, relax, and choose a book to read on the deck!

A comfortable living area features a light-colored sofa and two blue chairs arranged around a wooden coffee table. Natural light enters through multiple windows, and wall art adds a touch of charm. A ceiling fan is positioned above, enhancing the relaxed ambiance.

4.97 out of 5 average rating, 78 reviews

The Cottage - Green Mountain Getaway

Minutes to the Mountain Top and access to the VAST system! You'll feel right at home in this 2 bedroom, 2 bath cabin with 1 car garage. There is a large eat in kitchen equipped with everything you need. This cozy home is nestled on 60 private acres with Vermont’s world-class snowmobile trails right outside your door. Killington is 20 minutes away, Pico is 10 minutes away and the picturesque Mountain Top Inn is 5 minutes away!

4.96 out of 5 average rating, 690 reviews

The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.

Apartment in Rutland

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

4.91 out of 5 average rating, 126 reviews

A cozy living room area is presented with a dark gray sofa adorned with white pillows. A television is positioned on a light-colored console, with framed black-and-white nature photographs displayed on the wall. Natural light filters through the windows, enhancing the serene environment.

Home in Pittsford

Convenient Vermont Getaway

Conveniently located near the top ski and mountain bike attractions, incredible trails, resorts, and the towns of Woodstock, Middlebury, Killington, Pico, and Rutland. This historic property has been in existence since 1832 and has been lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. This one bedroom apartment is located downstairs in the two story duplex.

4.93 out of 5 average rating, 221 reviews

A snow-covered pathway leads to a charming white house surrounded by trees blanketed in snow. The structure features a gabled roof and a small cupola, with snow drifts framing the entrance. The clear blue sky provides a bright contrast against the winter scene.

Home in Pittsford

Colburn's Carriage House

Only 30 minutes from Killington/Pico ski resorts, and 20 minutes from Mountain Top Inn and Chittenden Reservoir, Colburn's Carriage House is a charming and convenient getaway. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

An open living area features warm wood paneling and a spacious bar area with two high stools. A dartboard is mounted on the wall adjacent to a window, while large windows allow natural light to brighten the space. Comfortable seating arrangements are visible in the background.

5.0 out of 5 average rating, 40 reviews

Maple Mountain Lodge - 3 bedroom home

Welcome to Maple Mountain Lodge! We are two sisters who are passionate about traveling and being exceptional hosts to our guests. This newly renovated & comfortable home is the perfect space for your family or group of friends to stay 20 minutes to Killington Mountain, 10 minutes to Pico Mountain, 5 minutes to Mountain Top Inn, 5 minutes to Chittenden Reservoir & so much more.

Popular amenities for Chittenden vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chittenden

5.0 out of 5 average rating, 29 reviews

Apartment in Pittsford

Fox Farm · Hilltop Retreat Near Mountains & Lakes

A charming mountain retreat is seen blanketed in fresh snow. The two-story home features a light-colored exterior with window shutters, surrounded by snow-covered landscaping. The private deck, accessible from the house, overlooks a serene winter landscape, framed by trees and distant mountains.

4.93 out of 5 average rating, 28 reviews

Mountain Top Getaway Killington, Pico, VAST Trails

4.96 out of 5 average rating, 47 reviews

A living area features a wooden sideboard and a television, complemented by a decorative rug with intricate patterns. Soft lighting from the adjacent dining area enhances the spacious feel, while a ceiling fan is visible in the background.

Apartment in Pittsford

Norm's Place

4.84 out of 5 average rating, 19 reviews

Apartment in Mendon

Killington Vermont Ski Hideaway

5.0 out of 5 average rating, 20 reviews

A spacious house is set on a lush green lawn, surrounded by trees and manicured shrubs. The charming porch wraps around the residence, offering views of the nearby hills. Bright blue skies create a serene backdrop for this inviting outdoor space.

Home in Pittsford

Pastoral Pittsford Home

A gas fireplace is positioned centrally within the living space, featuring a polished glass front that displays flickering flames. Exposed wooden beams and warm tones from the brick surround create a cozy ambiance, while a glimpse of the dining area with wooden chairs is visible in the background.

4.94 out of 5 average rating, 33 reviews

Blue Ridge Retreat-Hot tub/Mtn.Top/Killington/VAST

4.98 out of 5 average rating, 44 reviews

A spacious living area features a large leather sectional sofa facing a glass coffee table. Natural light floods in through multiple large windows, framed by dark trim. A cozy reading nook is seen in the corner, adorned with a decorative throw and a small side table.

Home in Pittsfield

Skyeburst | Modern Mtn Home