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Compare 466 Vacation Homes in Pittsford with updated reviews, rates, and availability.

Beautiful 4-Bedroom Home beside Middlebury College
Front view from street.

Beautiful 4-Bedroom Home beside Middlebury College

9.8 out of 10, Exceptional, (41)
"Great place and location!"
Beautiful 4-Bedroom Home beside Middlebury College
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Exterior

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

10.0 out of 10, Exceptional, (40)
"The owner was extremely easy to work with and even more responsive. The house has an AMAZING view Killington. Very clean and once you get the cast iron stove to temp it worked really well to heat the house. The sauna, and foosball table worked well. The hotub was easy to use, it fits 3 full size adults with no issue. The kitchen fridge had plenty of condiments, dressing and sauces. A really nice treat was that the beverage fridge was stocked with prev renters' drinks as well we added to it for...
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

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

9.8 out of 10, Exceptional, (17)
"This is a beautiful property with beautiful views, lots of indoor and outdoor space for the little ones to play, and for the adults to chill and socialize. Very clean and well kept. We would love to come back and stay here again in the future!"
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Pristine and private location, directly on Great Eastern Trail with snow-making!!

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

9.2 out of 10, Wonderful, (31)
"Clean house and glad we were able to bring our dog. Close to so many great mountains and rivers to explore. Great shower pressure. Wish there were some picnic tables or outdoor eating spaces on the sunny property."
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Interior

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

10.0 out of 10, Exceptional, (63)
"This house was perfect for our group of twelve. We were three families with kids ranging in ages from 6-14yrs old. There was enough space for everyone to relax after a day of skiing. The kitchen was very well stocked and had everything we needed. The ski hill is only a 5 mins drive. We would definitely stay here again"
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

9.8 out of 10, Exceptional, (9)
"My family and I stayed for a week at this home. The pictures do not do this home justice! It was very clean, well equipped with everything we needed and very spacious. The beds were really comfortable, showers were really nice and everything was stocked with all the essentials. We cooked breakfast every morning and dinner a few evenings and had everything we needed. Check in process was easy and all the details were clearly defined for checkout (also easy). The property is nice and private with...
The price is SAR 1,148
SAR 2,843 total
includes taxes & fees
2 Dec - 3 Dec
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

8.8 out of 10, Excellent, (18)
"The place is surrounded by nature and one can feel at peace with everything."
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Spectacular opportunity to enjoy the finest property in Killington Summit
Outside view in the wintertime.

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (19)
"We had a group of old friends that together for the weekend. The house was gorgeous, had a ton of room and was a lot of fun. Just a very warm, fun and relaxing place to be. There are a number of spaces that are great for gathering and plenty of awesome amenities and games for fun. "
Spectacular opportunity to enjoy the finest property in Killington Summit
S'Mookie the Bear- ski on and off, hot tub, pool
Bask in the sunlight in our spacious living room, filled with ample seating for all.

S'Mookie the Bear- ski on and off, hot tub, pool

9.0 out of 10, Wonderful, (2)
"Wonderful four bedroom place that fit our family well. Very well stocked for cooking. Easy walk to ski in/ ski out."
S'Mookie the Bear- ski on and off, hot tub, pool
The Ridge Chalet, an A-Frame Killington home
Exterior

The Ridge Chalet, an A-Frame Killington home

10.0 out of 10, Exceptional, (55)
"The property fit our needs to a tee. The owner thought of everything you would need. All we had to do is pack our clothes and we were set. Kitchen had everything you need, along with spices and even a few things in the refrigerator. Soaps and shampoo was provided just as if you were at a hotel. The main living area was very large and had plenty of seating, while the basement served as a living and sleeping quarters for the younger ones in the group. Very nice set up and owners were very...
The Ridge Chalet, an A-Frame Killington home
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Living area

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

9.8 out of 10, Exceptional, (21)
"Everything was clean and comfortable and had a great view from the living room/primary bedroom. Because we were there for a wedding we didn't use the kitchen or really get to enjoy all the amenities but the proximity to Woodstock was an added bonus. The shower head in the shared bathroom could use updating but really that's a small complaint. All in all we had a great stay."
Quiet Modern Luxury Home w/ Memory Foam Beds, FAST WiFi and Full Kitchen
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

9.4 out of 10, Exceptional, (25)
"Beautiful property with amazing view of the lake the directions were a little off according to the website but we found it very enjoyable and relaxing stay"
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC
Relax by "The Water's Edge" & enjoy amazing views and year round fun! 6BR/3.5BA
Exterior

Relax by "The Water's Edge" & enjoy amazing views and year round fun! 6BR/3.5BA

10.0 out of 10, Exceptional, (6)
"I booked this house based primarily on its location (easy access to a lake/hikes); size (we needed lots of room for 10 people); and availability. This fit our requirements, and when we got there, exceeded our expectations. Our family loved everything about the home and property from its location in a quiet lakeside community to its décor and spaciousness and all the amenities inside or outside. The location is central to some nice hikes. Crystal Beach is just around the corner, literally. The...
Relax by "The Water's Edge" & enjoy amazing views and year round fun! 6BR/3.5BA
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

9.0 out of 10, Wonderful, (78)
"Property was nice and location was great even for an of season stay. Lots of fun close by like the killington adventure center & visiting small toes like Woodstock & ludlow. Also hiking close by!! We were a bit disappointed that the indoor pool & hot tub were closed until the peak winter season so may mention that in the listing. We loved having the fire place & sauna inside unit. "
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
HappyCub! Hot tub, game room, fire pit!
Sink into our inviting living room, where laughter begins and memories are made.

HappyCub! Hot tub, game room, fire pit!

10.0 out of 10, Exceptional, (14)
"We had a great stay at the Happy Cub! Comfortable, clean and spacious for our group. The hosts were very communicative in order to assure our check-in and stay were smooth and we could enjoy our get away. Thank you!"
The price is SAR 929
SAR 2,418 total
includes taxes & fees
2 Dec - 3 Dec
HappyCub! Hot tub, game room, fire pit!
The Brandon Inn - King Room
Exterior

The Brandon Inn - King Room

8.4 out of 10, Very Good, (5)
"The Branford Inn was a historic hotel that despite its age was very nice."
The price is SAR 582
SAR 740 total
includes taxes & fees
3 Dec - 4 Dec
The Brandon Inn - King Room
☆ SKI ON & OFF ☆ Spruce Glen A on Great Eastern Trail w/AC, Sauna, Fireplace
Pristine, private location - directly on Great Eastern Trail with snowmaking!!!

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

9.2 out of 10, Wonderful, (30)
"We had a wonderful stay! The location was ideal, the property was cozy with lovely amenities, and our hosts were great communicators! Thank you!!!"
☆ SKI ON & OFF ☆ Spruce Glen A on Great Eastern Trail w/AC, Sauna, Fireplace
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace
Private, large lot and house in picturesque Killington

Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace

10.0 out of 10, Exceptional, (42)
"Great house close to the mountain. Very clean with everything needed for our stay. Owner was very responsive. Highly recommend. "
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace
Sweet chalet with private hot tub, firepit, game room & minibar

Sweet chalet with private hot tub, firepit, game room & minibar

9.6 out of 10, Exceptional, (35)
"All good lots of fun"
Sweet chalet with private hot tub, firepit, game room & minibar
Killington ski house
Plenty of Snow and Plenty to do: outside and in!

Killington ski house

9.6 out of 10, Exceptional, (31)
"Great place, great location, great response and communication with the host, Dean. Very much appreciated. "
Killington ski house
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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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, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (220)
"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "
Cozy Loft for two with Hot Tub
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.