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Holiday houses in Pittsford

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Top-rated holiday rentals in Pittsford

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

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Guest favourite
Condo in Killington
4.88 out of 5 average rating, 260 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

Top Guest favourite
A charming one-bedroom cabin is nestled among tall trees in a forested area. The wooden exterior is complemented by a porch with a railing and flower pots, creating a rustic appeal. Natural light filters through the windows, enhancing the cabin's tranquil setting.
Tiny home in Castleton
4.99 out of 5 average rating, 119 reviews

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Top Guest favourite
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, 245 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.

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
4.94 out of 5 average rating, 141 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

Superhost
The charming tiny house is illuminated by warm string lights, showcasing its welcoming entrance. A cozy wooden door with a decorative wreath invites guests inside, framed by multiple windows allowing for natural light. The surrounding trees accentuate the peaceful outdoor setting.
Tiny home in Pittsford
4.94 out of 5 average rating, 199 reviews

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. 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 favourite
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
4.9 out of 5 average rating, 117 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 favourite
Farm stay in Salisbury
4.95 out of 5 average rating, 417 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 favourite
A cozy living area is presented with a gray sofa and a black coffee table. Natural light enters through a window covered by light curtains. A television is mounted on the wall opposite a sleek media console, contributing to a comfortable ambiance.
Home in Pittsford
4.93 out of 5 average rating, 104 reviews

Upstairs Adventurer's Retreat

Welcome to this peaceful and centrally-located space in historic Pittsford. Situated near the top ski and mountain bike attractions in central Vermont, incredible trails, Middlebury, Rutland, Killington, Pico, Mountain Top Resort, and 45 minutes east of Woodstock, this couldn't be in a better location. This property has been in existence since 1832, and lovingly maintained with a backdrop of the Adirondacks beyond the picturesque pasture. Small but comfortable.

Top Guest favourite
Home in Clarendon
4.95 out of 5 average rating, 325 reviews

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Top Guest favourite
A charming white schoolhouse is surrounded by a blanket of fresh snow, with snow-covered bushes outlining the property. A tree stands bare nearby, while an American flag is displayed on the facade. The scene conveys a serene winter atmosphere in a quiet setting.
Home in Rutland
5 out of 5 average rating, 154 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.

Guest favourite
Apartment in Rutland
4.84 out of 5 average rating, 250 reviews

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Guest favourite
Apartment in Rutland
4.96 out of 5 average rating, 658 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.

Popular amenities for Pittsford holiday rentals

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