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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
An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.
Guest suite in Lake Bomoseen
4.97 out of 5 average rating, 237 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Guest favorite
A wooden deck is featured in the foreground, leading to a small sitting area with a patterned chair beside a black side table. Lush greenery surrounds the space, providing a natural setting, while a gravel path and stacked firewood are visible in the background.
Tiny home in Clarendon
4.9 out of 5 average rating, 251 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

Top guest favorite
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
4.94 out of 5 average rating, 129 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

Top guest favorite
The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.
Farm stay in Salisbury
4.95 out of 5 average rating, 408 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Top guest favorite
A welcoming farm sign displays 'Des Marais Farm' alongside an illustration of a red barn and fields. Colorful flowerbeds filled with red and pink blooms enhance the entrance, framed by lush greenery and a clear blue sky.
Farm stay in Brandon
4.95 out of 5 average rating, 105 reviews

The Swallows Nest in a wildlife preserve

NEW THIS YEAR: High speed internet, Heat pumps for heat and AC throughout the house, and a new refrigerator/ freezer Secluded and beautiful, at the end of a gravel dead end road, the Swallow’s Nest is part of our organic farm and wildlife refuge. You’ll find serenity here with huge open vistas. We are two miles from the town of Brandon. Brandon has restaurants, shops, art galleries and music venues. Check out what’s happening in Brandon at the Brandon area chamber of commerce.

Top guest favorite
A spacious living area features a light grey sectional sofa with cozy throw pillows. Natural light floods in through large glass doors that open to the yard, while a modern ceiling fan hangs above. A rug defines the seating arrangement, and simple decor adds warmth.
Cabin in Rochester
4.95 out of 5 average rating, 491 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.

Top guest favorite
The exterior of the converted schoolhouse is visible, surrounded by a blanket of fresh snow. Snow-covered bushes line the property, and a flag is displayed by the entrance. Leafless trees provide a serene contrast against the winter landscape.
Home in Rutland
5 out of 5 average rating, 145 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, 653 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
Apartment in Poultney
4.94 out of 5 average rating, 376 reviews

Cozy Poultney Village Apartment

I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

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, 210 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.

Top guest favorite
A cozy bedroom features a spacious bed with a white quilt and decorative pillows. Natural light enters through two windows, illuminating the room's soft blue walls. A bedside table with a lamp is positioned next to the bed, adding functional charm to the space.
Apartment in Chittenden
5 out of 5 average rating, 273 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont.

Top guest favorite
Apartment in Castleton
4.97 out of 5 average rating, 113 reviews

Castleton Cottage

This is a newly renovated first floor one bedroom apartment. It has all the amenities of home including a walk-in shower, full kitchen, and a pull-out sofa. It is within walking distance of Lake Bomoseen and its many amenities, including boat rentals and creemees. This is a non-smoking unit. Please let us know if you have any questions.

Popular amenities for Pittsford vacation rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Pittsford