Search Holiday Rentals in Pittsford

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Pittsford holiday rentals

Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is 7.341.048 ₫
8.001.742 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Robert Frost Mountain Cabins
Condo, 2 Bedrooms | Exterior
Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
Killington
The price is 5.900.729 ₫
17.443.257 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Fall Line Condos by Killington VR - 2 Bedrooms
Restaurant
Mountain Green Resort

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
The price is 22.329.382 ₫
32.563.594 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Mountain Green Resort
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is 5.009.805 ₫
11.299.426 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Suites at Killington Center
Indoor pool
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is 5.578.144 ₫
7.482.802 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Mountain Green
Condo, 1 Bedroom | Exterior
Mountain Green Resort by Killington VR - 1 Bedrooms

Mountain Green Resort by Killington VR - 1 Bedrooms

Mountain Green Resort by Killington VR - 1 Bedrooms
3.5 star property
Killington
The price is 4.122.301 ₫
12.518.049 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Mountain Green Resort by Killington VR - 1 Bedrooms
Condo, 2 Bedrooms | Dining
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo

Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo

Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
3.5 star property
Killington
The price is 7.228.696 ₫
19.196.173 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
Condo, 2 Bedrooms | Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is 5.445.532 ₫
17.410.262 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Woods by Killington Vacation Rentals - 2 Bedrooms
Condo, 2 Bedrooms | Sauna
Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo
3.5 star property
Killington
10.0 out of 10, Exceptional, (1)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
Fall Line Condo D4 2 Bedroom Condo
Condo, 2 Bedrooms | Sauna
Mountain Green Condo 2b4 2 Bedroom Condo

Mountain Green Condo 2b4 2 Bedroom Condo

Mountain Green Condo 2b4 2 Bedroom Condo
3.5 star property
Killington
The price is 6.133.327 ₫
17.480.420 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Mountain Green Condo 2b4 2 Bedroom Condo
House, 2 Bedrooms | Exterior
Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home
3.0 star property
North Sherburne
The price is 5.673.130 ₫
17.082.496 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Bob's Sled Lodge 2 Bedroom Home
Condo, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Pico Mountain Condo F106 3 Bedroom Home

Pico Mountain Condo F106 3 Bedroom Home

Pico Mountain Condo F106 3 Bedroom Home
3.0 star property
Killington
The price is 8.177.243 ₫
21.603.053 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Pico Mountain Condo F106 3 Bedroom Home
Condo, 4 Bedrooms | Dining
Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
The price is 10.074.339 ₫
25.159.479 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Sunrise Bear Ridge C4 4 Bedroom Condo
House, 2 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is 7.797.824 ₫
17.332.855 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Killington A-frame 2 Bedroom Home
House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
The price is 11.971.434 ₫
27.958.750 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Blue Haven 3 Bedroom Home
House, 3 Bedrooms | Living area
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
Killington
The price is 10.908.955 ₫
28.218.753 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Condo, 2 Bedrooms | Interior
Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo

Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo

Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo
2.0 star property
Rutland
The price is 4.762.472 ₫
15.795.840 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo
House, 3 Bedrooms | Interior
Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home

Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home

Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home
3.0 star property
Killington
The price is 5.976.508 ₫
18.490.016 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Left Duplex Home Directly Across From Pico Mountain, Close To Killington. 3 Bedroom Home
Condo, 3 Bedrooms | Exterior
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
2.0 star property
Killington
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Condo, 3 Bedrooms | Private kitchen
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo

Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo

Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo
2.0 star property
Killington
The price is 8.139.354 ₫
21.449.458 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsford Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Hotel staff was top shelf!!! Ate at the bar. Flatbread was great! And beer was ice cold !!! Great hotel definitely will stay here again!!"
Andy 1-night trip
Posted 2 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Frequently asked questions

Can I find a holiday rental in Pittsford?

Yes, there are holiday rentals close to the most popular sights in Pittsford, or you can select a more secluded option if you're looking for a relaxing 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 can I see and do in Pittsford?

Cultural attractions include New England Maple Museum, whereas Green Mountain National Forest is a spot to enjoy nature. In the wider area, you’ll find Proctor-Pittsford Country Club and Taconic Mountains Ramble State Park.

What’s a holiday rental in Pittsford like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsford. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for small groups.