Pittsford Holiday Rentals

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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 HK$1,976
HK$2,154 total
includes taxes & fees
4 Jan - 5 Jan 2026
Robert Frost Mountain Cabins
Aerial view
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 HK$1,762
HK$2,363 total
includes taxes & fees
21 Dec - 22 Dec
Mountain Green
Property grounds
Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is HK$887
HK$1,830 total
includes taxes & fees
12 Jan - 13 Jan 2026
Ben & Jerry’s Studio | 10 Min to Killington
Private kitchen
The Suites at Killington Center

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is HK$2,023
HK$3,937 total
includes taxes & fees
22 Dec - 23 Dec
The Suites at Killington Center
Smart TV, fireplace
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
2.0 star property
Killington
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
The price is HK$4,733
HK$8,561 total
includes taxes & fees
22 Dec - 23 Dec
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Indoor pool
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (44)
"Quick trip to and from Killington mt"
United States
Phillip F.
The price is HK$669
HK$2,275 total
includes taxes & fees
21 Dec - 22 Dec
Clean & bright condo with mountain views & modern kitchen - walk to lifts
3 bedrooms, desk, iron/ironing board, travel cot
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
The price is HK$1,782
HK$4,706 total
includes taxes & fees
13 Jan - 14 Jan 2026
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
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
"I had trouble getting in and out of the inner roads around the buildings and had to wait to use my rental car until the bus traffic cleared Old Mill Rd. to slush. This made me kind of locked in, but the bus service to and from the ski lodges did make it possible to ski. And that was the main reason I stayed at Mountain Green Resort the proximity and shuttle service."
United States
Scott
The price is HK$5,017
HK$8,805 total
includes taxes & fees
28 Dec - 29 Dec
Mountain Green Resort by Killington VR - 1 Bedrooms
Restaurant
Mountain Green Resort

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
The price is HK$4,756
HK$7,598 total
includes taxes & fees
24 Dec - 25 Dec
Mountain Green Resort
Smart TV, fireplace, video games, books
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is HK$1,820
HK$4,775 total
includes taxes & fees
20 Dec - 21 Dec
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Dining
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool

Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
2.0 star property
Killington
10.0 out of 10, Exceptional, (30)
"Great ski-in, ski-out property."
United States
Kristi C.
The price is HK$3,603
HK$6,957 total
includes taxes & fees
22 Dec - 23 Dec
Ski-In/Ski-Out Sunrise Village Condo | 2BR, Fireplace, Pool
Interior
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
2.0 star property
Killington
The price is HK$2,277
HK$4,592 total
includes taxes & fees
24 Dec - 25 Dec
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Exterior
Luxury Farmhouse Near Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Near Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Near Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (8)
"Stayed here for a long weekend and the house was perfect. Plenty of room, well stocked kitchen, so much to keep the kids entertained and close proximity to lots of activities. Hiked Okemo and Killington, visited Buttermilk Falls and explored Ludlow. Will go back for sure!"
United States
Jill B.
The price is HK$3,992
HK$8,915 total
includes taxes & fees
7 Jan - 8 Jan 2026
Luxury Farmhouse Near Okemo w/Hot Tub & Fire Pit!
Indoor pool, a heated pool
Modern Mountain Condo with Spa

Modern Mountain Condo with Spa

Modern Mountain Condo with Spa
The Woods
9.8 out of 10, Exceptional, (8)
"The property met our expectations. Great property for parties less than 6 people."
United States
Michael H.
The price is HK$1,484
HK$3,392 total
includes taxes & fees
21 Dec - 22 Dec
Modern Mountain Condo with Spa
Property grounds
Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is HK$2,208
HK$4,520 total
includes taxes & fees
12 Jan - 13 Jan 2026
Gnome Home Mountain Ski Chalet w/Sauna Killington
Terrace/patio
Wade`s World Ski Home FirePlace Shuttle location

Wade`s World Ski Home FirePlace Shuttle location

Wade`s World Ski Home FirePlace Shuttle location
2.0 star property
Killington
9.6 out of 10, Exceptional, (5)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
The price is HK$1,740
HK$4,014 total
includes taxes & fees
20 Dec - 21 Dec
Wade`s World Ski Home FirePlace Shuttle location
Interior
A charming 1820's farmhouse

A charming 1820's farmhouse

A charming 1820's farmhouse
Woodstock
10.0 out of 10, Exceptional, (29)
"Beautiful home. It was a good location for my family to attend a family wedding at the Woodstock Inn."
United States
Robin H.
The price is HK$7,033
HK$11,368 total
includes taxes & fees
12 Jan - 13 Jan 2026
A charming 1820's farmhouse
Pool
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 HK$3,284
HK$7,045 total
includes taxes & fees
22 Dec - 23 Dec
Mountain Green Condo 2b4 2 Bedroom Condo
1 bedroom, desk, iron/ironing board, free WiFi
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Dining
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
3.0 star property
The Woods
9.8 out of 10, Exceptional, (6)
"Very clean and well equipped condo! We enjoyed our stay."
United States
Tanya W.
The price is HK$3,415
HK$6,601 total
includes taxes & fees
22 Dec - 23 Dec
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
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.
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Top Pittsford Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Wonderful experience definitely would stay again."
Ariel 3-night trip
Posted 3 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Find out more about Pittsford

Search for holiday rentals in Pittsford on Expedia! You can easily find your home rentals, villas, holiday apartments in Pittsford using one of the methods below:

  • View our selection of featured holiday rentals in Pittsford
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  • Enter your travel dates to view the best deals on holiday rentals in Pittsford while they last

Look no further and take a look at our great range of rental properties in Pittsford!

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 are some of the best holiday rentals that Pittsford has to offer?

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!: This holiday home rental outside of Pittsford is located near skiing, and has a patio, a selection of games and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.