Vacation rentals in Pittsford

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Top-rated vacation rentals in Pittsford

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Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 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.

Jun 11 – 18

ﺩ.ﺇ439 per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 128 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

Jul 25 – Aug 1

ﺩ.ﺇ437 per night

Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 117 reviews

Mi Casa es su Casa!

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 TV, surround sound system. Wi-Fi access. 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. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Dec 22 – 29

ﺩ.ﺇ429 per night

Guest favorite

Cottage in Leicester

4.97 out of 5 average rating, 243 reviews

Banjo's Cottage near Middlebury & Recreation Areas

Private getaway on our organic garlic farm with sunroom, wood stove, fully equipped kitchen & wifi. Walk to Fern Lake, wander our woods trails, explore the Moosalamoo National Recreation Area. Kayak on Lake Dunmore, bike the back roads and Green Mountain trails. Fifteen minutes to Rikert Nordic Center, Blueberry Hill, and Middlebury Snow Bowl; less than an hour from Killington, Sugarbush & Mad River ski areas. Easy access to Middlebury College, local breweries & top tier restaurants.

Jan 20 – 27

ﺩ.ﺇ611 per night

Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 222 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. * We are following the guidelines set up by the W.H. O. and we are leaving a window between reservations to disinfect our suite due to Covid-19.

Mar 20 – 27

ﺩ.ﺇ475 per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 585 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Nov 18 – 25

ﺩ.ﺇ511 per night

Guest favorite

Apartment in Pittsford

4.99 out of 5 average rating, 116 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike in the warmer weather. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

Jun 4 – 11

ﺩ.ﺇ396 per night

Guest favorite

Cabin in Fair Haven

4.97 out of 5 average rating, 151 reviews

Private and cozy cabin with Lake Bomoseen views!

Secluded yet only a few minutes from all amenities with Wifi! Close to Bomoseen State Park, Glen Lake, boat launches, and stores! Perfect place to stay if you don't want to camp with the rest of your group at the state park, overflow from a place on the lake, visiting the college, or just a beautiful get away. Large deck to enjoy the views, screen porch, fireplace, even a short hiking trail around the property! Two well behaved dogs ok for small cleaning fee.

Dec 25 – Jan 1

ﺩ.ﺇ509 per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 388 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.

Jan 11 – 18

ﺩ.ﺇ512 per night

Guest favorite

Guesthouse in Castleton

4.97 out of 5 average rating, 231 reviews

Bomoseen Bungalow

Located near Lake Bomoseen and Castleton University. This is a charming upstairs apartment in a quiet, residential neighborhood. Walking distance to boat rentals and to a local country store. This apartment provides you with a cozy stay - a bedroom with a queen size bed, sofa bed, and air mattress. There is Roku television, a heat pump for air conditioning or heat, Keurig coffee maker, and more. This is a non smoking unit.

Oct 17 – 24

ﺩ.ﺇ322 per night

Guest favorite

Apartment in Rutland

4.96 out of 5 average rating, 522 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, 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.

Jun 12 – 19

ﺩ.ﺇ364 per night

Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 146 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 bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

May 17 – 24

ﺩ.ﺇ344 per night