Search Vacation Homes in Pittsford

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
2 Jum. I - 4 Jum. I
In two weeks
9 Jum. I - 11 Jum. I
In one month
23 Jum. I - 25 Jum. I
In two months
20 Jum. II - 22 Jum. II

Compare 590 Vacation Homes in Pittsford with updated reviews, rates, and availability.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (22)
"House is 1 minute or less from the Skye Peak Gondola, which as convenient for skiing. Clean house, has lots of room and games for families. Hot tub was really nice too."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Cozy Private Bedroom with Own Entrance - No Shower
Exterior

Cozy Private Bedroom with Own Entrance - No Shower

10.0 out of 10, Exceptional, (3)
"This place is a nice, cozy little getaway. Great location!! Host has thought of every little accoutrement one might need when you're away from home, everything from hand lotion to a French press!! This was my second stay here, definitely won't be my last!! Love it!"
The price is SAR 300
SAR 458 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Private Bedroom with Own Entrance - No Shower
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Exterior

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

9.2 out of 10, Wonderful, (36)
"Fantastic location for easy ski on ski off."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Fridge, microwave, oven, stovetop

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

10.0 out of 10, Exceptional, (51)
"Fantastic Vermont farm house in a great setting close to Okemo and Killington. Very accommodating, clean, warm and comfortable. After skiing we enjoyed just sitting around the fireplace and talking. We plan on returning next year."
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Exterior

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

10.0 out of 10, Exceptional, (3)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Exterior

The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA

The price is SAR 1,032
SAR 2,276 total
includes taxes & fees
27 Apr - 28 Apr
The Shredquarters: Mid-Century Modern Chalet | 4 minutes to Snowshed 3BR/2BA
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Fridge, microwave, oven, stovetop

Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

9.6 out of 10, Exceptional, (25)
"If you're looking for the perfect getaway near Killington, look no further than this incredible rental home! From the moment we stepped inside, we were blown away by how spacious and welcoming the property felt. It easily accommodated our large group, with plenty of room for everyone to relax and enjoy themselves.The home has such a cozy, homey atmosphere that made it hard to leave! We spent our evenings gathered around the real fireplace, which added so much warmth and charm to the experience....
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Fridge, microwave, oven, stovetop

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn

10.0 out of 10, Exceptional, (1)
"Was an amazing location with tons to do. Clean property and cozy!"
Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Fridge, microwave, oven, stovetop

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

9.6 out of 10, Exceptional, (20)
"Great place for our guys weekend. Place was clean and beds were comfortable. Would definitely rent again."
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Fridge, microwave, oven, stovetop

Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen

9.8 out of 10, Exceptional, (32)
"Clean house with food amenities and great location."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
TV, fireplace

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

8.6 out of 10, Excellent, (25)
"Cool location, perfect basic ski house"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

9.6 out of 10, Exceptional, (119)
"The house was great for our large gathering of multiple families with kids. The commercial range with griddle was awesome and made cooking for the group so much easier. The house had multiple living spaces so it allowed a few in the group that had to work during the week to find a nice space away from the main group. Proximity to Killington was great!We were there during the Presidents Day holiday week so our check in got delayed (5pm) and check out was a bit early (10am), but totally...
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Spectacular 4 Bed Killington Home
Exterior

Spectacular 4 Bed Killington Home

9.8 out of 10, Exceptional, (118)
"This is our second year in a row renting this house. Plenty of room for 2 families of four and the location to Killington ski are is perfect. The wood stove is great for drying out ski gear and plenty of room for cooking and eating for 8. Communication with Wally was clear and responsive. Another great ski getaway!"
Spectacular 4 Bed Killington Home
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
Fridge, microwave, stovetop, dishwasher

Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.

9.8 out of 10, Exceptional, (53)
"Spacious, clean, excellent property for families.2 hot ins and 2 livings rooms help give everyone their own space Fireplace creates cozy ambiance "
Sunburst home sleeps 18 with an indoor and outdoor hot tub. Perfect for family reunions and getaways.
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
Exterior

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

10.0 out of 10, Exceptional, (82)
"Place was great. Spacious, clean and killer views. Kitchen is modern and well equipped making meals was easy. Very quiet location but still convenient to Killington/Pico. "
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts
FiddleHead Lane-Near Killington, Fireplace, Grill
Fridge, microwave, oven, stovetop

FiddleHead Lane-Near Killington, Fireplace, Grill

10.0 out of 10, Exceptional, (3)
"We came up to Killington for a weekend of skiing and to enjoy all that the mountain has to offer. The house was perfect for our group. It was clean and comfortable. It had everything we needed and ample sleeping space. It was close enough to the mountain to get there quickly. The owners were extremely accommodating and always responded to any questions we had. They made us feel at home. We would definitely stay here again. "
FiddleHead Lane-Near Killington, Fireplace, Grill
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
Terrace/patio

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (14)
"Such a nice weekend stay. We arrived late Friday night and woke up to a beautiful view of Lake Dunmore. The house was clean and welcoming. The kitchen had all one needed. The weather was not in our favor (rained most of the weekend) but it did not matter. It was a perfect spot for our quick weekend to Midd. "
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
***Air Conditioned Beautiful Rental*** Right Off Killington Access Road
Exterior

***Air Conditioned Beautiful Rental*** Right Off Killington Access Road

10.0 out of 10, Exceptional, (37)
"Wonderful stay! Great location "
***Air Conditioned Beautiful Rental*** Right Off Killington Access Road
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Exterior

5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!

9.4 out of 10, Exceptional, (13)
"The Good: great location. Owners were highly responsive and helpful when we had questions/concerns. The beds are super comfy and the hot tub is very nice.The Not So Good: for such a high price, there is not much offered outside of the location and nice beds. We were unable to use multiple TVs in the house since the batteries in the remotes were dead. The water is well water and tastes/smells bad to the point some of us were gagging at the taste. They had a water cooler which was nice, but that...
5 BR Duplex with Hot Tub & Firepit 1 minute from Killington Resort!
Spacious home 3 mins to slopes, trails & restaurants. Great for large groups.
Living area

Spacious home 3 mins to slopes, trails & restaurants. Great for large groups.

10.0 out of 10, Exceptional, (3)
"The house was clean and comfortable. While a bit dated, it had everything we needed and was perfectly set up for spending time together while providing plenty of space for everyone to have down time. It was very relaxing. The location was easy and convenient."
Spacious home 3 mins to slopes, trails & restaurants. Great for large groups.
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.
Don't see what you're looking for?
See all available properties in Pittsford
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsford

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ultimate relaxing vacation

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (189)
"Very relaxing stay in a cozy cabin with a beautiful view of the pond."
The price is SAR 525
SAR 672 total
includes taxes & fees
12 May - 13 May
Ultimate relaxing vacation
Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (236)
"My wife and I stayed in "The Little Loft" for a ski trip to Sugarbush. The cabin it small for sure but offers everything you will need from a standpoint of short term livability. We used that hot tub daily / nightly after skiing all day, had a great meal we grilled out and had a few nice bonfires as well. If you do not want to have to drive 30 minutes for dinner or shop for your food and cook it, then you may find it a small inconvenience but for us we intentionally wanted to be in a quiet cabin...
Cozy Loft for two with Hot Tub & Mtn Views
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.