Search Vacation Homes in Pittsford

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Vacation Homes in Pittsford

Water front home with large two tiered deck! 2 bathrooms 😂

9.4 out of 10, Exceptional, (105)
"My family enjoyed their stay very much. "
Water front home with large two tiered deck! 2 bathrooms 😂

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

10.0 out of 10, Exceptional, (6)
"Lovely rustic and cozy cabin stay"
Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

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

10.0 out of 10, Exceptional, (111)
"Clean and great location!"
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Ski house 8 min from the mountain

9.6 out of 10, Exceptional, (20)
"House was cozy, had great facilities, the location was perfect and the owner was very responsive to any questions. Definitely would visit again. "
Ski house 8 min from the mountain

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (56)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College

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

8.4 out of 10, Very Good, (28)
"The host and house manager are absolutely the best. Felt very taken care of - they went above and beyond."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

9.8 out of 10, Exceptional, (26)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

New Listing - Luxury log home with stunning views

10.0 out of 10, Exceptional, (31)
"We had a great time enjoying this beautiful home!! Great for family getaways!!"
New Listing - Luxury log home with stunning views

Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

10.0 out of 10, Exceptional, (42)
"Our granddaughter was getting married at Lake Bomoseen, only a short 3 or 4 minute ride from this beautiful house. We had our 4 grandchildren and their parents with us, this house let us spread out and have fun. We did not have good weather but that didn't stop my 8 year old granddaughter from jumping in the lake. We wish we could have enjoyed the outside more, but with a rainy weekend, we were so happy we had the expanse of this home. We played charades, games, made puzzles. This home has...
Totally remodeled year round LAKEFRONT home with stunning views of Lake Bomoseen

Perfect Woodstock Getaway! Lovely Riverside Home

9.8 out of 10, Exceptional, (8)
"We had a wonderful weekend at Charlie's house. The property was clean and welcoming and the fenced in backyard was excellent for our dog Riley"
Perfect Woodstock Getaway! Lovely Riverside Home

BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

10.0 out of 10, Exceptional, (1)
"This place is amazing! Great location. Very smooth check in and check out . Good communication with owners. Very clean and new! "
BRAND NEW: Beautifully Restored Timber Frame Barn w/ Hot Tub & Movie Theater

Cottage on east side of Lake Bomoseen, on-site boat slip included

9.6 out of 10, Exceptional, (14)
"Wonderful"
Cottage on east side of Lake Bomoseen, on-site boat slip included

Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12

10.0 out of 10, Exceptional, (29)
"Wonderful weekend with friends. 10 minute drive to lifts and close to a few restaurants. Plenty of space at the house to spread out and relax"
Snowberry Hill, 5 bedroom, Private Luxury Ski Home on Killington Mtn, sleeps 12

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

10.0 out of 10, Exceptional, (84)
"It's a grand old house and the property is beautiful."
Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (66)
"The perfect place for our friends and family to stay!"
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

9.6 out of 10, Exceptional, (57)
"Cute house nestled in the woods, great location and private hot tub on the deck! We enjoyed every second of it!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer

BRIDGEWATER RETREAT

10.0 out of 10, Exceptional, (9)
"A true gem."
BRIDGEWATER RETREAT

3BR w Incredible View, Hot Tub & Sauna

10.0 out of 10, Exceptional, (6)
"Very nice unit. Plenty of space, and great views of the mountain. "
3BR w Incredible View, Hot Tub & Sauna

Luxury Condo Tucked in the Heart of Killington

The price is AED 371
AED 1,116 total
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo Tucked in the Heart of Killington

Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms

10.0 out of 10, Exceptional, (18)
"It was a wonderful stay in a beautiful home close to all of the places we wanted to spend time!"
Crisp and Clean Lakefront Home sleeps 8 in 4 Bedrooms
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsford Hotel Reviews