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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 469 Vacation Homes in Pittsford with updated reviews, rates, and availability.

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

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

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Living area flooded with natural light.

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
The price is AED 2,102
AED 4,027 total
includes taxes & fees
27 Jan - 28 Jan
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!
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, (20)
"Very peaceful & relaxing. "
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

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

9.8 out of 10, Exceptional, (48)
"We went up in December to Ski Okemo. This is a great house and has all amenities including an awesome fireplace and large eating area. Great location for two of three families to go away together and enjoy VT!"
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
Killington, Vermont Ski House w/ Hot Tub and Sauna
I Our snow country home welcomes you!

Killington, Vermont Ski House w/ Hot Tub and Sauna

9.4 out of 10, Exceptional, (84)
"Perfect house. This is our second time there and we had a wonderful experience."
Killington, Vermont Ski House w/ Hot Tub and Sauna
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
Welcome to your Ideal Killington Escape!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

10.0 out of 10, Exceptional, (16)
"We had two families stay at the home the first week of April during Spring Break so we could do a couple of days of skiing. The house was wonderful. It had so many beds, which made it great for the 6 kids and then separate bedrooms for the two couples, which was great. We enjoyed making a fire in the fireplace at the end of the day as we played board games with the family..we especially enjoyed playing LCR (Left Center Right). Kristin's communication was incredible. She was always so quick to...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Mountain Views from the minute you drive in to the house

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (22)
"Our family stayed at Evan's home because we were attending a wedding (conveniently up the road) at Mountain Top Resort. The home gushes with Vermont charm! It was beautifully and thoughtfully decorated which made our stay so cozy. Evan thought of everything- from exact GPS directions, to helpful notes around the home to help his guests be comfortable! Evan was very helpful at every stage of our stay! We would absolutely 100% recommend staying at Evan's beautiful home!"
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Limited-Time Discounted Deals | Private Hot Tub & Ping-Pong | Close to Ski

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

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

Peaceful house w/ mountain views, land, trails, fireplace, a/c, w/d, wifi, lawn
Stunning 4 bed Timber Frame Ski Retreat on 6 acres
Aerial view

Stunning 4 bed Timber Frame Ski Retreat on 6 acres

10.0 out of 10, Exceptional, (1)
"We had a great stay. Cozy post and beam with quick access to Okemo."
Stunning 4 bed Timber Frame Ski Retreat on 6 acres
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
Exterior

Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views

9.0 out of 10, Wonderful, (17)
"My friends and I enjoyed the house immensely. My husband loved the sauna, while my friends enjoyed the hot tub. The kitchen was well equipped and had everything we needed to prepare meals for 16 people. Lots of space for a large group. Small issue with the deck furniture but was resolved immediately. Very impressed with Irina and her responsiveness to queries. Recommend very highly."
Luxury 7BR/6.5BA Mountain Retreat with Sauna, Hot Tub, and Stunning Views
The Brandon Inn - Fourth Floor Queen Room
Point of interest

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is AED 533
AED 679 total
includes taxes & fees
26 Jan - 27 Jan
The Brandon Inn - Fourth Floor Queen Room
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, (43)
"We had such a wonderful stay! The home owner was happy to greet us and show us the rooms and how to use the fireplace and hot tub. The home is warm, cozy and inviting. It was the perfect stay for our group of ladies looking to enjoy the slopes together! "
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Resort townhome with on-site pool, hot tub & easy ski access

Resort townhome with on-site pool, hot tub & easy ski access

9.0 out of 10, Wonderful, (66)
"This is our third stay in Killington VT and every time we have stayed in the Woods development. It is quiet and relaxing but close to everything we need. The fall colors are also wonderful. The home we stayed in was a bit dated but was clean, secure, and very comfortable for our week-long stay. It had modern amenities, a fully equipped kitchen, and was more than enough space for two people. The sauna and whirlpool tub were also great. Communication with the host (Vacasa) was very good, and we...
Resort townhome with on-site pool, hot tub & easy ski access
Roundabout Ridge
Dining

Roundabout Ridge

9.2 out of 10, Wonderful, (21)
"The property was advertised. The outdoor stairs and driveway felt a little dangerous after the snow Killington has had recently but management sent some to clean the stairs and the driveway after we made them aware. The home has a lot of character but could use some upgrades. Otherwise, we had a good time and look forward to coming back again. "
Roundabout Ridge
Middlebury Gem open concept and 5 minutes from town
Exterior detail

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (70)
"House is a perfect option for families visiting Middlebury College. Spacious, clean, and well appointed!"
Middlebury Gem open concept and 5 minutes from town
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
Ski on ski off on Great Eastern Trail!!!

Perfect Ski in Ski Out House with Fireplace & Hot Tub!!

10.0 out of 10, Exceptional, (78)
"This place was AS Advertised. Can easily fit 2-3 families. Fantastic location. Ski right off the driveway onto Great Eastern down to the Skyship gondola. The house is clean, linens were provided and were nice. Hot tub outside has a beautiful view of mountains. The fire place inside was idyllic and there was plenty of firewood and starter logs. The place is the perfect New England ski spot. In the summer there is a nice fire pit and sitting area with a swing in the back. The owner/manager...
Perfect Ski in Ski Out House with Fireplace & Hot Tub!!
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, (65)
"This home was absolutely beautiful. Great location as well. We had a group of 11 friends and family who have skied together, some for over 40 years. Even a 7 year old. It was perfect! Everyone had their own space, we could all dine together, hang out together, or not. It was perfect. We highly recommend "
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
Cozy private country setting - 15 miles from Woodstock
Perfect 4 season get away

Cozy private country setting - 15 miles from Woodstock

10.0 out of 10, Exceptional, (25)
"We were in Vermont on the most unfortunate of circumstances. It was a pleasure to come back to this unit. It was clean and comfortable. The kitchen and bathrooms were well appointed. They had done an excellent job remodeling this building. It was warm and the sheets were some type of flannel that was welcome for our 11F nights. Good views of the mountain on the other side. "
Cozy private country setting - 15 miles from Woodstock
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

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, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub
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, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ultimate relaxing vacation
Breathtaking , relaxing and private haven. Perfect for unwinding from busy life

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (181)
"Our goal was to unplug a bit, play games, watch movies and explore a new VT town during our 2 night stay. Our expectations were fully met! We enjoyed spending a day in Middlebury and all of our time in the cabin. It was nice to have wifi access as well! We look forward to coming back during the warmer weather! "
The price is AED 514
AED 658 total
includes taxes & fees
27 Jan - 28 Jan
Ultimate relaxing vacation
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.