House holiday rentals in Pittsfield

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Top-rated house rentals in Pittsfield

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Top Guest favourite
The exterior of the cottage features a warm wood facade with red accents. Large windows allow natural light to fill the interior. A spacious deck is visible, equipped with a grill and outdoor seating, providing a comfortable area to enjoy nature.
Home in Granville
4.96 out of 5 average rating, 150 reviews

Epic Views of the Green Mountains

Luxurious bohemian style overlooking one of the most epic views in the Green Mountains. Surrounded by 25,000 acres of National Forest and complete seclusion, yet just a short ride from several towns. Spacious, immaculate, modern home with rustic beams and gorgeous wood floors. Each of the three bedrooms (and baths!) have a wonderful view. The master bedroom is massive and has sweeping views out over the Battell Wilderness and the Long Trail. The front of the cottage is a wall of windows overlooking a beautiful pond and the Green Mountain National Forest. No light pollution. No noise except for the tree frogs and the sound of the White River rushing over the rocks far below in the hollow. It's worth mentioning that Breadloaf Mountain Cottage was a gift that I am grateful for. I still can't believe that I am so lucky to be able to enjoy it frequently. Please understand that those sweeping, epic views you see all around you when you are there, come at a price. Being perched atop a mountain in the wilderness has obvious benefits, but due to frequently changing weather, access and utilties are sometimes a bit more tricky than something in town. Please be prepared to be patient with the weather and the WIFI. While my internet is as good as anywhere in Vermont, it is a rural network and is likely more quirky than urban or suburban utilities. I have a 20mbps service. Breadloaf Mountain Cottage is at the top of a ridge that runs parallel to scenic Route 100. It sits at about 1600 feet above sea level. While completely secluded, it is just 1.3 mile to the Granville Store, and just a few minutes more to Hancock, Rochester and Warren. You could spend weeks just exploring the hiking, biking, swimming and fishing opportunities right from the property! Breadloaf Mountain Cottage is located on Forest Road 55, just off scenic Route 100. While it is easily accessible year round, a 4X4 or AWD vehicle is highly recommended in snow and mud. Quality AT or snow rated tires are a must in the winter. This is true generally in Vermont. Come prepared.

Top Guest favourite
A vintage gas station building features a white exterior with red lettering spelling 'TEXACO.' Large glass windows line the front, showcasing a clear view of the interior. The American flag is displayed prominently, and a tree-lined background adds a touch of greenery.
Home in Castleton
4.93 out of 5 average rating, 116 reviews

Cozy Contemporary Downtown Texaco

Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Guest favourite
A verdant meadow is visible, dotted with grazing cows. The background features rolling hills showcasing trees adorned in autumn colors, transitioning from green to warm shades of red and orange. The serene landscape is framed by a distant mountain range under a clear sky.
Home in Rochester
4.97 out of 5 average rating, 103 reviews

Bill’s Barn Rochester Vermont 3 Bdrm entire house

Our place is a 1980's barn/woodshop that never housed animals that has been converted into a lovely three bedroom home.We are 20 minutes from Rikert 2019 hosts of the Bill Koch Festival and the Middlebury College Snow Bowl.The place is light and airy with southern and eastern sun.The main living room has 13 foot ceilings with lots of couches, arm chairs and places to hang out, read and or relax.We are in the heart of the Green Mountains with skiing and colleges, an easy drive from the house.

Guest favourite
A spacious living area features large windows that provide views of the surrounding greenery. A comfortable sectional sofa, accented with pillows, is positioned near a wooden coffee table. A cozy armchair is placed beside a floor lamp, creating a warm and inviting seating space.
Home in Killington
4.94 out of 5 average rating, 131 reviews

Glamorous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

Superhost
A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.
Home in Stockbridge
4.87 out of 5 average rating, 147 reviews

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

Guest favourite
A spacious deck features wooden flooring and railing, surrounded by trees. Two wooden lounge chairs face a breathtaking view of the Green Mountains, providing an open space to relax and enjoy the natural scenery.
Home in Rochester
4.91 out of 5 average rating, 302 reviews

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

Top Guest favourite
A large house with a gray exterior features a welcoming front porch and a gabled roof. Surrounding greenery includes trees and flower bushes, creating a peaceful outdoor environment. The driveway is visible, leading to the house amid a spacious lawn.
Home in Bethel
4.86 out of 5 average rating, 170 reviews

Affordable, private, surrounded by flower gardens

Enjoy the summer in beautiful Vermont. The guest area is the entire main floor of a large house with my quiet second home above. Private entrance, 2 bedrooms, full bathroom with washer and dryer, speedy fiber optic internet. The open kitchen has full sized stove and fridge with good cookware and appliances, adjacent to a large open living area. On a paved scenic road. Go up to Silver Lake for a swim, head out on any of the back roads for a run or a ride.

Top Guest favourite
A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.
Home in Rochester
4.97 out of 5 average rating, 214 reviews

The Guest House at Sky Hollow

This quiet 120 acre hilltop house on an 1800's farm turned homestead offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Guest favourite
An aerial view highlights a secluded mountain farmhouse surrounded by lush greenery and rolling hills. The expansive 60+ acre property features a blend of fields and forests, with the distant Green Mountains visible under a partly cloudy sky.
Home in Pittsfield
4.86 out of 5 average rating, 111 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.

Top Guest favourite
The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.
Home in Rutland
5 out of 5 average rating, 143 reviews

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

Superhost
A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.
Home in Pittsfield
4.84 out of 5 average rating, 240 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.

Guest favourite
A warm and inviting living area features a comfortable couch with a blanket draped over it and a classic wooden coffee table. A red armchair complements the space, while a grand piano and vibrant oriental carpet add character. Natural light enters through multiple windows.
Home in Leicester
4.95 out of 5 average rating, 185 reviews

Pristine Cottage, Grand Piano, Massage Studio

Meticulously clean, custom built cottage with grand piano & massage studio on property. Beam ceilings, wood floors, oriental carpets, & lots of art. Complete Kitchen Shower with shampoo, conditioners & body wash provided. New private deck, tables & chairs... outside art work. Swedish Massage with steamed towels & hot stones available in log cabin on site discounted to $70 for visiting guests

Popular amenities for Pittsfield house rentals

Quick stats about house rentals in Pittsfield

  • Total rentals

    40 properties

  • Nightly prices starting at

    $216 AUD before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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