Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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Top guest favourite

Guest suite in Stockbridge

5 out of 5 average rating, 100 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Superhost

Chalet in Stockbridge

4.84 out of 5 average rating, 164 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Guest favourite

Treehouse in Hancock

4.98 out of 5 average rating, 125 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling perfect for any admirer of a beloved wizarding world, or anyone who just truly appreciates a isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled among the branches of several maple trees, providing a magical and secluded escape from the hustle and bustle of everyday life.

Guest favourite

Cabin in Pittsfield

4.98 out of 5 average rating, 160 reviews

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

Guest favourite

Tiny homes in Warren

4.99 out of 5 average rating, 247 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Guest favourite

Home in Pittsfield

4.85 out of 5 average rating, 107 reviews

A million-dollar view near Killington on 60 acres.

This secluded 200 + year old mountain farmhouse is located in the small town of Pittsfield, VT just 5 minutes away from one of the most scenic drives in New England, Route 100. Surrounded by national forest with stunning views of the Green Mountains, this is the perfect place to get away with family or even by yourself. Plenty of room outside on the 60+ acre property with fields and a small pond. In the center of Vermont, it's the perfect home base.

Superhost

Home in Pittsfield

4.9 out of 5 average rating, 174 reviews

Beautiful Mountain Log Cabin with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from killington and pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 481 reviews

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Guest favourite

Home in Pittsfield

4.84 out of 5 average rating, 238 reviews

Killington area home - 4-seasons & hot tub

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

Top guest favourite

Apartment in Hancock

4.96 out of 5 average rating, 161 reviews

Suite in the Green Mountains

We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

Top guest favourite

Home in Killington

4.98 out of 5 average rating, 117 reviews

CozyDen - AC, Grill, Bike to Mountain!

Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!

Guest favourite

Treehouse in Bethel

4.98 out of 5 average rating, 113 reviews

Crooked Maple Treehouse

Nestled in the heart of the Vermont Green Mountains, the Crooked Maple Treehouse is handcrafted from timber harvested and milled on-site by the owner, Brett. Thoughtfully crafted to create a rustic and cozy retreat. Take this opportunity to escape your busy everyday life to appreciate the simplicity and solitude of living off the grid at the Crooked Maple.