Holiday rentals in Pittsford

4.88 out of 5 average rating, 26 reviews

Home in Bolton

The Bumble Bear Inn, Bolton Ldg

ElizabethRating, 5 stars2 months ago

This is our second annual visit to the Bumble Bear Inn. We love all the TVs and WiFi but especially the game room! Kitchen is well-stocked and morning coffee in the sunroom is very relaxing. Great place to visit in the winter! Kim and Cameron are very responsive and great!

5 out of 5 average rating, 5 reviews

Cottage in Mendon

The Mendon Cottage: Cozy Home. Killington / Pico

SeanRating, 5 stars2 months ago

The Mendon Cottage is clean, cozy and private. It’s just a 15 minute drive to Killington base, even in a fairly decent snow storm. There are trails behind the property that offered some good hiking for our doggo (they’re made for snowmobiles, but we didn’t spot one during our stay). The property delivers on its main promise: a less pricey alternative to staying at Killington, with very little inconvenience for the ski bums. Unless you simply can’t live without the ability to take the shuttle and ski off the mountain to your rental, you really can’t go wrong with this property. (It snowed our entire stay and the private road and driveway were plowed repeatedly and always navigable.)

5 out of 5 average rating, 40 reviews

Cabin in Lake George

Great location. Walk to Village attractions/beach!

MarinaRating, 5 stars4 months ago

Katrina was a wonderful host! She was responsive and thoughtful with her recommendations. The home was incredibly clean and had everything you could need for your stay and more. We felt very comfortable in the space and were so impressed with how well the space was maintained and that no detail was overlooked to make guests feel at home. The location was great and the lake views were beautiful at night with the holiday lights! Highly recommend Katrina and the cabin!

4.91 out of 5 average rating, 100 reviews

Cabin in Bridgewater

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars2 months ago

Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.

Guest suite in Lake George

4.95 out of 5 average rating, 79 reviews

Lake George Perfect Location

StephenRating, 5 stars4 weeks ago

Peter was a great host! His house is in a great location! My wife and I went to Lake George for a long weekend without our kids. It was our first time away from our kids in 5 years and Peter made the experience perfect! Peter was always willing to help. His place is super clean and well maintained! My wife and I are already planning a trip back! Thank you Peter!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Pittsford holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pittsford's top sights

Mountain Top Inn & Resort24 locals recommend

New England Maple Museum5 locals recommend

Hubbardton Battlefield State Historic Site8 locals recommend

Taconic Ramble State Park14 locals recommend

Vermont Marble Museum and Gift Shop8 locals recommend

Hathaway Farm6 locals recommend

Other great holiday rentals in Pittsford

5 out of 5 average rating, 12 reviews

Home in Wells

Breathtaking Lakeside Retreat!

BrianRating, 5 stars2 months ago

Second year renting. Great place, definitely would recommend. Hope to return next year. Brooke is a fantastic host. Thank you

4.75 out of 5 average rating, 92 reviews

Apartment in Killington

Still 89 Trails Open, Low, Low Rates

RyanRating, 5 stars1 month ago

Convenient to the slopes via the shuttle that picks up out front. Able to walk to a good restaurant, Still on the Mountain. Place is comfortable and has everything we needed for a weekend skiing.

4.8 out of 5 average rating, 15 reviews

Cabin in Barnard

Private post & beam log cabin on Macintosh Pond.

NinaRating, 5 stars4 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

5 out of 5 average rating, 6 reviews

Cabin in Hudson Falls

Cozy Retreat Near LG – Private

MaximusRating, 5 stars1 month ago

Such a pretty estate!! Loved staying here. Woohoo!!

5 out of 5 average rating, 8 reviews

Home in Chittenden

Modern Retreat next to Mountain Top Inn,Killington

MaddyRating, 5 stars2 months ago

I couldn't recommend this place more! My cousins and I had a great time and Uli is super attentive. The hot tub has a great view of the lake, it was also salt water which I love. The space was extremely cozy and exactly what we needed. We snowboarded pico and killington and it was about a 25-30 minute ride. We will for sure be back! Thank you guys so much!

5 out of 5 average rating, 16 reviews

Home in Plymouth

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars2 months ago

Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!

4.96 out of 5 average rating, 27 reviews

Apartment in Killington

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC

ChrisRating, 5 stars1 month ago

What a great place. It was very enjoyable for the whole family. There were plenty of board games, and an arcade game (packman along with many other old game's to choose from). It was sleek, it was spotless and had everything we needed. We loved the area and spa. Thanks and we will hopefully see your great place again soon.