Holiday rentals in Pittsford

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Top-rated holiday rentals in Pittsford

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Top guest favourite

Tiny home in Castleton

4.99 out of 5 average rating, 107 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

Guest suite in Lake Bomoseen

4.96 out of 5 average rating, 197 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 favourite

Apartment in Mendon

4.93 out of 5 average rating, 107 reviews

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY Elegant - Cozy - Spotless Our condo is located minutes from Pico & Killington, 🥾AT&LT, 💍wedding venues, 🚴‍♀️mountain biking, ⛳️golf and many local events. Superhost level comfort welcomes you! OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️Pico -5 minutes ⛷️Killington -15 minutes 🥾Minutes from LT/AT •Squeaky Clean •Fireplace, TV, WIFI •Seasonal Pool(towels provided) •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21yrs)

Top guest favourite

Yurt in Pittsford

4.96 out of 5 average rating, 137 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 favourite

Guest house in Wallingford

4.98 out of 5 average rating, 699 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!

Top guest favourite

Home in Rutland

5 out of 5 average rating, 138 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

Flat in Rutland

4.86 out of 5 average rating, 185 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.

Top guest favourite

Guest house in Castleton

4.97 out of 5 average rating, 321 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.

Top guest favourite

Flat in Rutland

4.96 out of 5 average rating, 610 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.

Guest favourite

Home in Pittsford

4.94 out of 5 average rating, 196 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 favourite

Guest suite in Castleton

4.98 out of 5 average rating, 127 reviews

Vermont Hill Top Studio

You can see the stars from your Bed at Night - Studio space with a private entrance located on the quiet eastern end of our house. Twelve foot window provides spectacular views of Bird Mountain, & Killington, Pico Castleton is located in a great central location which acts as a great launching point for Lake Bomoseen , Killington / Pico Resort , or exploring the state

Top guest favourite

Flat in Chittenden

5 out of 5 average rating, 248 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.

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Other great holiday rentals in Pittsford

Guest favourite

Apartment in Killington

5 out of 5 average rating, 18 reviews

Cozy Slopeside Studio at Pico

SamanthaRating, 5 stars2 months ago

After being disappointed by the weather (lack of snow), we were SO happy we chose to stay here with Cole and Rachel. We spent most of our time cuddled on the couch watching movies and felt right at home. We loved it!

Top guest favourite

Cabin in Goshen

4.97 out of 5 average rating, 34 reviews

Scenic Vermont Green Mountain Retreat

DawnRating, 5 stars2 weeks ago

Best vacation I've had in years. I have traveled quite a bit but never used Airbnb before. I included this in my initial message. Darren made sure to give clear and precise instructions that made everything from start to finish so easy and comfortable. The pics don't do the property justice. As beautiful as the photos look, in person everything is magnified by a hundred. My two pups also loved VT and they really enjoyed chasing each other around the property. If you would be so kind as to host us again, we would definitely be back!!

Top guest favourite

Farm stay in Clarendon

5 out of 5 average rating, 67 reviews

Dream Catcher Farm

Deborah JRating, 5 stars3 weeks ago

Deanna was a SuperHost as if the word was created for her. I, especially, felt at home. She's delightful, caring and sweet. Deanna's family and her dog Bella are so very welcoming. Bella should be listed as SuperHost #2! Her home is peaceful & beautiful > during the early mornings, there's multitudes of birds which made my Merlin (Bird Identifier) App go wild, including uncommon and rare birds. At night from the deck, viewing white tail deer and a BIG blue heron, and fall asleep with frog murmurs. The location perfectly afforded me several options of my intended adventures (kayaking a different lake each day.) The accommodations and its location, made my daily excursions easy to prepare for each night and leave the day to simply explore and enjoy my day. Location is everything. This was my 2nd time visiting here; and this will be one of MY places to go. CYA in July Deanna!

Guest favourite

Flat in Pittsford

4.97 out of 5 average rating, 33 reviews

Norm's Place

SamuelRating, 5 stars4 months ago

Nice clean place to stay and excellent communication from the hosts. The property matches what's described. We were skiing all day and was a good spot to crash. It was bit further from Killington than we wanted, but that was clear up front!

Guest favourite

Home in Chittenden

4.98 out of 5 average rating, 42 reviews

Green Mountain Getaway

VinodRating, 5 stars1 month ago

We had a very restful and comfortable stay. There were plenty of hiking spots within a 30 min drive. And lots of food options in Rutland nearby. We will definitely consider staying here again when we visit the area in the future.

Guest favourite

Cabin in Brandon

5 out of 5 average rating, 6 reviews

Emrose Luxury Cabin

VeronicaRating, 5 stars3 months ago

great host. very responsive and accommodating, pleasure staying with them

Guest favourite

Guest house in Hubbardton

4.95 out of 5 average rating, 56 reviews

Flatlanders Outpost on Lake Beebe

JohnRating, 5 stars1 week ago

Just wanted to say thank you for hosting our stay, the apartment was everything we were hoping for and more.. a beautiful place in a quiet and secluded area, we truly loved it and would come back! 5 stars for a great stay!

Top guest favourite