Pittsford Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Pittsford

Ultimate relaxing vacation
9.8 out of 10, Exceptional, (152)
"Very quiet, very spacious, huge outside deck. "
The price is CA $191
CA $238 total
includes taxes & fees
Jun 17 - Jun 18
Ultimate relaxing vacation
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (32)
"Will be back!!"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Studio | Aerial view
Killington Center Inn & Suites by Killington VR - Studios
3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
The price is CA $136
CA $466 total
includes taxes & fees
May 24 - May 25
Killington Center Inn & Suites by Killington VR - Studios
Fridge, microwave, oven, stovetop
Luxurious Secluded Cottage Massage Studio on Site
10.0 out of 10, Exceptional, (34)
"Beautiful cottage equipped with everything you might need. Incredibly clean, comfortable and a helpful, friendly host."
The price is CA $225
CA $330 total
includes taxes & fees
May 27 - May 28
Luxurious Secluded Cottage Massage Studio on Site
TV, fireplace, DVD player
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
9.6 out of 10, Exceptional, (46)
"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Classic Vermont Cabin on 2.5 acres Lake Frontage
9.8 out of 10, Exceptional, (91)
"We can not say enough wonderful things about our stay. Brian was there to meet us and do a walk though of the property and even helped us out with local places to go. He is a gem! Although it rained it was absolutely perfect. The yard gave our pups a place to run free but there was also cute areas to walk them all around the area. The views of the water are incredible. Just sad it was too cold to jump in... maybe next time. October was the perfect time to see all the leaves changing and breathe...
Classic Vermont Cabin on 2.5 acres Lake Frontage
Property grounds
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
9.2 out of 10, Wonderful, (13)
"Great little cabin - really enjoyed our stay"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Exterior
Cozy Studio for 4 - Walk to Mountain w/ Balcony
9.0 out of 10, Wonderful, (12)
"Great location. Hot tub, salt water pool, steam room and sauna were welcomed after a day on Superstar! Beautiful locker rooms and facilities. Easy drop off of “schlep” at the parking garage to the room. Bus carts available too. We would definitely stay again."
The price is CA $115
CA $264 total
includes taxes & fees
May 27 - May 28
Cozy Studio for 4 - Walk to Mountain w/ Balcony
Indoor pool, outdoor pool
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Property grounds
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC
9.4 out of 10, Exceptional, (20)
"There was so clean, comfy, and relaxing!"
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC
Exterior
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
9.4 out of 10, Exceptional, (56)
"We came into town to see our friend play a two night show at Pickle Barrel. The place was perfect. Check in info was thorough and easy. Kim was great. She was responsive to communications and very accommodating. Would definitely stay here or one of her other properties again!"
edgemont 3 bedrooms wood fireplace updated baths ski home on shuttle sleeps 8
Fridge, microwave, oven, stovetop
Vermont Lake House
10.0 out of 10, Exceptional, (7)
"The house was clean and full of extras such as a multi function game table, shelves of assorted boxed games & cards. There was a large deck with a large BBQ. All the rooms a large family would need. Clean and functional kitchen. A responsive owner that was immediately available for any questions. The view of the lake was delightful. If you find yourself in the Poultney VT. vicinity, this is the place to stay."
Vermont Lake House
Exterior
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
10.0 out of 10, Exceptional, (144)
"Beautiful/nicely appointed home. The house had everything in it to make for a very comfortable stay and the hosts were so gracious, helpful, and communicative. We didn't want to leave and already can't wait to make a return trip! Thanks, Angelo and Deb!"
Cozy Family-friendly Log Cabin With 25ft Interior Fireplace + Modern Amenities.
Desk, free WiFi, bed sheets
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
8.8 out of 10, Excellent, (38)
"Great location within just a few miles of Killington base made our spring skiing getaway nice. The unit was as advertised clean with a comfortable king size bed, adequate room, and convenient parking. We especially like the privacy, nestled up top in this community off the access road. The icing on the cake for us was an excellent pool, a lab pool, and hot tub that we made grade use of enjoy your stay, will be back again!"
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Aerial view
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
10.0 out of 10, Exceptional, (7)
"We loved the condo. We stayed for a school break, family of three and it was just what we needed to unplug from our busy life. Easy to get everywhere. We will definitely rent it again on our next trip."
The price is CA $188
CA $469 total
includes taxes & fees
May 24 - May 25
The Swirl Suite at Killington: Brand New Remodeled 1 BR/2BA Suite 142
Indoor spa tub
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (12)
"Wonderful location located just south of the slopes. A bit of a walk to the lift but doable and fantastic trail to ski home. Very clean, loft area was a great addition. Very nice to have complimentary shampoo/conditioner/soap and dishwasher and laundry detergent. Everything we need for baking/meals. Lots of extra pillows!"
Trail Creek 33 | Condo in Killington
Don't see what you're looking for?
See all available properties in Pittsford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pittsford Vacation Rental Travel Info

Other types of properties in Pittsford you may be interested in

Terrace/patio
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.4 out of 10, Good, (1000)
"This was a wonderful stay. Everyone, from front desk check in, to bartender, to Starbucks barista were warm, inviting, friendly, and helpful. The room was spotless. Appointed as advertised, and well cared for each day. I was pleasantly surprised and impressed overall. "
The price is CA $178
CA $196 total
includes taxes & fees
Jun 5 - Jun 6
Killington Mountain Lodge, Tapestry Collection by Hilton
Indoor pool
Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, (1004)
"No USB"
The price is CA $193
CA $212 total
includes taxes & fees
Jun 16 - Jun 17
Comfort Inn Trolley Square
Outdoor pool, a heated pool
The Mountain Inn at Killington
2.5 star property
9.2 out of 10, Wonderful, (573)
"We had a fantastic stay. The customer service is excellent on all levels, the lodge is clean and comfortable, the views are breathtaking and the food at the restaurant is delicious. We will definitely be back when we are back in the area. "
The price is CA $196
CA $227 total
includes taxes & fees
May 29 - May 30
The Mountain Inn at Killington
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Pittsford. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Pittsford?

Yes, there are vacation rentals close to well known points of interest in Pittsford, or you can select a more remote option if you want a relaxing place to stay. Pittsford is known for its ski areas and shopping. Make sure you have time to check out the restaurants and museums during your trip.

What are some of the best vacation home rentals in Pittsford?

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC: This vacation home rental outside of Pittsford is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a pool table.

How many vacation rentals are there in Pittsford?

Expedia has 7 vacation rentals for your stay in Pittsford.

What can I see and do in Pittsford?

While exploring the area, visit family-friendly sights like Pond Hill Ranch and Pro Rodeo, or get outside and enjoy nature at Lake Bomoseen. New England Maple Museum and Proctor-Pittsford Country Club are other places to visit while you're in town.

What’s a vacation rental in Pittsford like?

Vacation rentals are private properties you can book for a short or long stay in Pittsford. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.

Recent reviews of Pittsford properties
Expedia verified reviews