Vacation rentals in Pittsford

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Top-rated vacation rentals in Pittsford

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The rustic farmhouse is set on a spacious green lawn, showcasing a classic red exterior with a metal roof. Large windows provide ample natural light, and the surrounding trees create a serene country atmosphere.
Apartment in West Rutland
4.91 out of 5 average rating, 139 reviews

Mountain View Apartment

Quiet, second floor, farmhouse apartment in country setting. Two connected bedrooms sleep four, one with a queen bed and the other with two twin beds. Watch the sunrise from the private deck or walk the fields to watch the sun set over the Adirondaks. Plenty of room to roam over the farm fields. Owner on property. 15 minutes from Castleton University. Please see more under "your property" -18 mi to Killington Resort/ 15 mi to Pico Ski Resort -9 miles to Rutland Regional Medical Center

Top guest favorite
Cabin in Poultney
4.94 out of 5 average rating, 401 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

Top guest favorite
A wooden deck offers seating with two lounge chairs, presenting expansive views of a field and distant mountains at sunset. The sky is painted in warm hues, while a solitary tree stands nearby, adding to the serene landscape.
Yurt in Pittsford
4.97 out of 5 average rating, 171 reviews

Remote Cozy Yurt with Sunset Views

Enjoy some time in a secluded yurt nestled in a quiet valley with spectacular sunset views. It comfortably sleeps 4, but can accommodate more. There is a bathhouse with an outdoor shower, compost toilet, and sink. Complete with propane stovetop, grill, and all necessary kitchenware. Stays in colder months will enjoy the warmth and comfort of a wood stove. Guests can also enjoy a small trail system on property for exercise or leisure. We hope you will come enjoy this peaceful retreat!

Top guest favorite
Home in Mendon
4.98 out of 5 average rating, 170 reviews

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.

Guest favorite
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
4.97 out of 5 average rating, 147 reviews

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.

Top guest favorite
A charming house with a light blue roof stands by a serene pond, surrounded by autumn foliage. Tall grasses frame the view, while a gently sloping landscape leads to the water's edge, providing a sense of tranquility in a natural setting.
Home in Proctor
4.98 out of 5 average rating, 60 reviews

Peaceful Pond View ~30 mins to Killington

Relax with the whole family while taking in beautiful views of this peaceful pond. Kayak, fish and swim in the warmer months, or hit the slopes in the snow. There are also a few hiking trails within walking distance. Close to many restaurants and only half an hour away from Killington/Pico. Close to Chittenden, Lake Bomoseen & Lake George. Enjoy the quiet and get cozy while relaxing and spending quality time with each other. Small dogs considered, but must get owner approval.

Guest favorite
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
4.96 out of 5 average rating, 47 reviews

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!

Top guest favorite
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
5.0 out of 5 average rating, 161 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.

Top guest favorite
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
4.96 out of 5 average rating, 690 reviews

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.

Top guest favorite
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
4.91 out of 5 average rating, 126 reviews

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.

Top guest favorite
Apartment in Pittsford
5.0 out of 5 average rating, 29 reviews

Fox Farm · Hilltop Retreat Near Mountains & Lakes

Between the mountains and the water — where every view feels like Vermont. Fox Farm: A bucolic hilltop retreat between the Taconic and Green Mountain ranges with stunning views in every direction. Equidistant from Lake Bomoseen and Killington, this thoughtfully designed apartment offers cozy interiors, curated artwork, and premium amenities. Come for the views — stay for the feeling.

Guest favorite
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
4.93 out of 5 average rating, 221 reviews

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.

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