Pittsford Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Pittsford vacation rentals

Exterior

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (41 reviews)
"Very nice place great owner"
United States
Joe
The price is ￥40,877
￥44,556 total
includes taxes & fees
May 31 - Jun 1
Robert Frost Mountain Cabins
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is ￥12,183
￥30,111 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Rutland Retreat
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (17 reviews)
"We wish there had been a recycle box. Also, mini split in living room didn’t work as well as the bedroom mini splits did for heat. Also, curtains/drapes on living room windows would be great and would help with heat loss."
United States
Jane
The price is ￥23,967
￥71,347 total
includes taxes & fees
Jun 3 - Jun 4
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is ￥20,543
￥44,768 total
includes taxes & fees
May 31 - Jun 1
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (77 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is ￥23,450
￥35,717 total
includes taxes & fees
May 31 - Jun 1
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is ￥26,515
￥84,990 total
includes taxes & fees
May 31 - Jun 1
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

Unique family-friendly Vermont cabin!

Unique family-friendly Vermont cabin!
Fair Haven
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay at a new and clean cabin. It was very cozy!"
United States
Emily J.
The price is ￥28,522
￥46,748 total
includes taxes & fees
May 30 - May 31
Unique family-friendly Vermont cabin!
Apartment (Trail Creek 05) | Interior

Trail Creek 05

Trail Creek 05
3.5 star property
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I ended up getting changed to another property trail creek 80. I wish I could give 10 stars! This place is amazing! Clean quiet spacious and so much more. I want to already book this same place for next years Spartan race!! Thank you for having an amazing property "
United States
Kimberly
The price is ￥25,569
￥64,365 total
includes taxes & fees
Jun 26 - Jun 27
Trail Creek 05
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is ￥11,785
￥29,788 total
includes taxes & fees
Jun 1 - Jun 2
Vermont Suite | 10 Min to Killington & Woodstock
Dining

Killington resort: Walk to Mountain, Biking & Pool

Killington resort: Walk to Mountain, Biking & Pool
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Excellent VRBO. Perfect location to the mountain. Condo was modern and clean and very comfortable. Would go back again!! "
United States
Sheri L.
The price is ￥18,231
￥52,323 total
includes taxes & fees
May 30 - May 31
Killington resort: Walk to Mountain, Biking & Pool
Property grounds

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is ￥24,222
￥60,838 total
includes taxes & fees
May 31 - Jun 1
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Exterior

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (58 reviews)
"Great stay. We really loved the ski in ski out feature. Host was responsive with any issues"
United States
Andrea W.
The price is ￥31,051
￥91,558 total
includes taxes & fees
Jun 1 - Jun 2
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Exterior

Adorable cabin with screened porch and private fire pit

Adorable cabin with screened porch and private fire pit
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful place to stay tucked away in the woods. The owners are extremely thoughtful and personable. Can’t wait to go back. "
United States
Sorin
The price is ￥47,985
￥64,670 total
includes taxes & fees
Jun 1 - Jun 2
Adorable cabin with screened porch and private fire pit
Terrace/patio

BlueBird Escape- Pool, Near Bike Park and Golf!

BlueBird Escape- Pool, Near Bike Park and Golf!
Killington
The price is ￥45,737
￥99,247 total
includes taxes & fees
May 30 - May 31
BlueBird Escape- Pool, Near Bike Park and Golf!
Fridge, microwave, oven, stovetop

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Property grounds

Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
Braintree
10.0 out of 10, Exceptional, (1 review)
The price is ￥50,594
￥67,901 total
includes taxes & fees
Jun 1 - Jun 2
Charming TREEHOUSE in remote location
Microwave, oven, stovetop, dishwasher

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is ￥47,775
￥107,972 total
includes taxes & fees
May 31 - Jun 1
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Golf

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage in the heart of Middlebury!
Middlebury
The price is ￥20,384
￥53,220 total
includes taxes & fees
May 31 - Jun 1
Purple Door Cottage in the heart of Middlebury!
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
"Picture Perfect!!"
Chandrashekhar 1-night trip
Posted 5 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton

Find out more about Pittsford

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

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?

Water front home with large two tiered deck! 2 bathrooms 😂: This vacation home rental outside of Pittsford is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 larger area, you’ll find Proctor-Pittsford Country Club and Taconic Mountains Ramble State Park.

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.