Search Chalets 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
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 36 Chalets in Pittsford with updated reviews, rates, and availability.

Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

10.0 out of 10, Exceptional, (107)
"Fun family get away!"
Log Home# w/ Incomparable Peace, Serenity, Privacy And The First Class Amenities

Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont

10.0 out of 10, Exceptional, (6)
"Relaxing stay in a great area."
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont

BearHaus- Central AC, HUGE Hot Tub, FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
BearHaus- Central AC, HUGE Hot Tub, FirePit

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (34)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

9.8 out of 10, Exceptional, (44)
"Great little cottage, highly recommend"
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

2.0 star property
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

South View Chalet!

9.2 out of 10, Wonderful, (26)
"The house was perfect for our group. The outdoor space was great and the view is beautiful. Would certainly stay here again!"
South View Chalet!

Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

10.0 out of 10, Exceptional, (1)
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

Mountain View Chalet Fabulous views large entertaining area just off Killington Road

10.0 out of 10, Exceptional, (1)
Mountain View Chalet Fabulous views large entertaining area just off Killington Road

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

10.0 out of 10, Exceptional, (1)
"Awesome property and very responsive staff! Highly recommended. "
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

8.8 out of 10, Excellent, (5)
"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

9.8 out of 10, Exceptional, (59)
"The house was beautiful and had great group spaces, we definitely recommend the property!"
Newly Renovated Rustic style home w/luxury bathrooms & mountain views, Sereni

The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

9.0 out of 10, Wonderful, (2)
"Stayed for a ski weekend and it was a nice quiet house on a quiet street but still situated close to the resorts."
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Great location close to Killington Ski Resort, about 8min drive to snow shed/ramshead. House was perfect for our group of 16. Plenty of space & bathrooms! Hot tub was great after long day of skiing & snowboarding. Herbie was quick to answer all our questions. Can't wait to go back next year!"
Killington Chalet - Great Space and Location!

Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort

10.0 out of 10, Exceptional, (5)
"This property is really nice and spacious. It is perfect for three couples as each bedroom is on a different level. It kept really warm and cosy, the kitchen is well-equipped and the games room is a real bonus! The location is great too - just a few minutes drive to the Killington base lodges - however one slight drawback is that it is right next to a main road and at night you can hear cars going by (not super loud though and not really a problem). Overall we really enjoyed our stay and we...
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

9.8 out of 10, Exceptional, (22)
"Our stay at Black Dog Lodge was truly great! It’s a beautiful lodge that had everything we needed. The layout was perfect and allowed everyone a space to hang and gather. It was a treat!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

BearVaria - AC, Hot Tub, Close to Trails!

10.0 out of 10, Exceptional, (9)
"Great quite location near restaurants and 5 mins from the slopes. The kids loved the little arcade area and the hot tub was great for after skiing. Furniture was a little outdated but met our needs for a fun family vacation"
BearVaria - AC, Hot Tub, Close to Trails!

The Overlook - Hot Tub, Game Room, 5min to MTN

10.0 out of 10, Exceptional, (2)
"We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski."
The Overlook - Hot Tub, Game Room, 5min to MTN

Secluded 2600 sqft home 15 min from Okemo and Killington

10.0 out of 10, Exceptional, (3)
"Nice & comfortable Great location between Killington & Okemo"
Secluded 2600 sqft home 15 min from Okemo and Killington

Relaxing retreat in the mountains 20 min to Killington

8.0 out of 10, Very Good, (2)
"This home was perfect for our family. Very clean and conveniently located between Woodstock and Killington. Would highly recommend to anyone with small kids!"
Relaxing retreat in the mountains 20 min to Killington
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

Other property types in Pittsford

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (189)
"We all had a wonderful time, enjoying this cozy, homey cabin, and the fantastic view over Perch Pond. We were comfortable inside, and took many walks outside... beautiful!"
The price is AED 514
AED 658 total
includes taxes & fees
12 May - 13 May
Ultimate relaxing vacation

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (237)
"Wonderful place "
Cozy Loft for two with Hot Tub & Mtn Views

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.