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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 26 Chalets in Pittsford with updated reviews, rates, and availability.

Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Front of the chalet that overlooks the lake

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

10.0 out of 10, Exceptional, (4)
"Very clean, great access to the water. Plenty of nice cooking gear, very happy with the experience, very clean and comfortable!"
Charming 2-bedroom + loft log cabin at Lake Bomoseen in Castleton, Vermont
Killington Chalet - Great Space and Location!
Exterior

Killington Chalet - Great Space and Location!

9.4 out of 10, Exceptional, (13)
"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!
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Bigelow Chalet, a spacious vacation home in a beautiful central location of Killington, Vermont.

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

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

9.8 out of 10, Exceptional, (32)
"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
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
West Park Chalet is a spacious six-bedroom house just off the access road, a mile from the base lodges and surrounded by restaurants, shops, and nightlife options.

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

2.0 star property
The price is AED 1,818
AED 4,648 total
includes taxes & fees
26 Feb - 27 Feb
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
South View Chalet!
Exterior

South View Chalet!

9.2 out of 10, Wonderful, (25)
"This house is great for large groups and a perfect location. But the cleaning fee is clearly just being pocketed as the house was dirty and messy when we arrived. It was clear the bedsheets had not been changed from the prior guests which was upsetting and a big turn off. Other areas of the house were also very messy. For the price thst is charged, I would expect this house to be immaculate. The movie theater was a huge hit, but has a very foul smell to it. The heat had not been turned on before...
South View Chalet!
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.

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.
BearHaus- HUGE Hot Tub, FirePit
Step inside and discover the largest hot tub in the area, a luxurious oasis designed to provide unparalleled comfort and relaxation. It's the perfect retreat after a day of adventure.

BearHaus- HUGE Hot Tub, FirePit

10.0 out of 10, Exceptional, (2)
"This beautiful, spacious home was perfect for our family reunion. We were 10 people: 4 couples, 2 singles, and 2 dogs. The bedrooms were very comfortable. The well-appointed kitchen, dining area and family room easily accommodated all of us. The location was lovely and quiet, yet only a few minutes drive from restaurants, shops and hiking trails. We had a wonderful weekend and would be happy to book again. Highly recommend. "
The price is AED 2,150
AED 4,646 total
includes taxes & fees
3 Mar - 4 Mar
BearHaus- HUGE Hot Tub, FirePit
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
Living area

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

10.0 out of 10, Exceptional, (4)
"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
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Living area

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

9.8 out of 10, Exceptional, (43)
"Have always wanted to stay in a chalet and now we have. Had a very nice time in a unit that was well equipped. Thank you Janie. "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
The Overlook - Hot Tub, Game Room, 5min to MTN
Outdoor spa tub

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

10.0 out of 10, Exceptional, (1)
"The property was so amazing. The description is accurate. We were comfortable, cozy, with privacy yet close to skiing. Melissa is a wonderful and attentive host!! I highly recommend staying here. We hope to be back in the winter!"
The Overlook - Hot Tub, Game Room, 5min to MTN
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

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

9.8 out of 10, Exceptional, (21)
"“We had a wonderful time staying here! The view was absolutely beautiful, and we truly enjoyed the peaceful setting. The kitchen could use some upgrades—some of the cookware was worn, and the oven needed a little extra cleaning. If you plan to cook a lot, bringing a few favorite pots might be helpful. That said, the location and overall experience made for a great stay, and we would love to visit again!”"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Cozy 3 Bedroom home near Killington
Living area

Cozy 3 Bedroom home near Killington

10.0 out of 10, Exceptional, (1)
"We booked this house as it was close to a friend’s 50th birthday party. The house was really great. Super clean, new fresh linens and great amenities. Steph, the owner was extremely communicative and I would absolutely recommend a stay here. Thanks so much, we will return."
Cozy 3 Bedroom home near Killington
Romantic Cozy Mountain Retreat near Killington
Bathroom

Romantic Cozy Mountain Retreat near Killington

10.0 out of 10, Exceptional, (6)
"Our stay in this house was amazing, everything was perfect as described and like pictures. 20 mins from Killington Mountain and Pico Mountain."
Romantic Cozy Mountain Retreat near Killington
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
Interior

Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly

9.4 out of 10, Exceptional, (8)
"Great stay, thanks!"
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
5-bedroom chalet walking distance to bars and restaurants - on the access road
Classic Vermont A-frame

5-bedroom chalet walking distance to bars and restaurants - on the access road

9.8 out of 10, Exceptional, (46)
"Communication was incredible"
5-bedroom chalet walking distance to bars and restaurants - on the access road
The Whimsical Chalet 3 Bedroom Chalet by RedAwning
Exterior

The Whimsical Chalet 3 Bedroom Chalet by RedAwning

3.0 star property
The Whimsical Chalet 3 Bedroom Chalet by RedAwning
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Living area

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

8.6 out of 10, Excellent, (4)
"Not as described "
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
BearVaria! Hot Tub, 2 miles to mountain

BearVaria! Hot Tub, 2 miles to mountain

10.0 out of 10, Exceptional, (9)
"We really enjoyed the amenities at this property in a very nice secluded part of Killington! Fire pit, hot tub, grill, some disc golf baskets, it really was what we needed for a weekend away mtn biking with the guys. The property is a little older, but well furnished and comfortable beds and towels. Definitely recommend staying here! Also, the hosts were super responsive texting back, usually within 15 minutes for any questions. They were extremely accommodating with an early check in and a...
The price is AED 2,356
AED 4,236 total
includes taxes & fees
6 Mar - 7 Mar
BearVaria! Hot Tub, 2 miles to mountain
Secluded 2600 sqft home 15 min from Okemo and Killington
Living area

Secluded 2600 sqft home 15 min from Okemo and Killington

10.0 out of 10, Exceptional, (3)
"We absolutely loved our time at this lovely rental! All amenities were as described. Beds were super comfy, sauna was terrific, kitchen was well equipped and the fireplace, cozy. Meg was super responsive. We would definitely rent again!"
Secluded 2600 sqft home 15 min from Okemo and 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.
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Other property types in Pittsford

Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views
Ultimate relaxing vacation
Breathtaking , relaxing and private haven. Perfect for unwinding from busy life

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (184)
"The cabin was pristine. The pond and surrounding woodland are breathtaking. Loved the drive in from the main road..so beautiful in the winter. A well needed reprieve from the daily grind. I would love to stay again in the summer months."
The price is AED 514
AED 658 total
includes taxes & fees
25 Feb - 26 Feb
Ultimate relaxing vacation
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
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.