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Compare 28 Chalets in Pittsford with updated reviews, rates, and availability.

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, (3)
"Not as described "
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

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

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

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted lift tix!

2.0 star property
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted lift tix!

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

9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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!

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

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

9.8 out of 10, Exceptional, (20)
"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.

Relaxing retreat in the mountains 20 min to Killington

8.0 out of 10, Very Good, (2)
"Our biggest issue is that the listing says 3 bedrooms, 1 with a queen, 1 with twin bunks, and 1 with a queen and 2 twins. But it’s actually a full with 2 twins—a bouncy, mushy full. The twins in that room are paper thin mattresses on boards and they felt a bit like 2x4’s, so I’d only recommend them for kids, even though they were roomy twins. This presented a major issue in our vacation. We surprised my older parents by inviting them for part of it and were happy to give them the queen. This...
Relaxing retreat in the mountains 20 min to Killington

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 4,006
AED 6,974 total
includes taxes & fees
23 Dec - 24 Dec
BearHaus- HUGE Hot Tub, FirePit

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

9.8 out of 10, Exceptional, (41)
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Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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...
BearVaria! Hot Tub, 2 miles to mountain

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

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

9.8 out of 10, Exceptional, (15)
"À l'occasion de mes 50 ans, je souhaitais découvrir les merveilleuses couleurs des feuilles d'automne dans le Vermont. Un rêve d'enfant ! Une partie de ma famille nous a accompagné mon épouse et moi. Ce chalet nous a offert tout le confort attendu. Calme, entouré d'arbres ce logis était "the best place to live" De plus, le billard, le sauna et le jacuzzi extérieur ont permis de nous détendre après nos nombreuses visites et lors des journées "off". Située non loin de l'autoroute 89 et de la...
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

Gnome Home Mountain Ski Chalet w/Sauna Killington

10.0 out of 10, Exceptional, (3)
"This was a wonderful property with every single we needed. It was probably the most well-stocked place I've ever rented!"
The price is AED 1,455
AED 2,633 total
includes taxes & fees
13 Jan - 14 January 2025
Gnome Home Mountain Ski Chalet w/Sauna Killington

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

10.0 out of 10, Exceptional, (3)
"This home was perfect in every way! We enjoyed staying here and there was easy communication with property management that was promptly handled. We will try to book when we decide to return to Killington."
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort

New Construction Timber Frame / Mins to mountain and restaurants / Amazing views

10.0 out of 10, Exceptional, (2)
"We couldn't have been more delighted with our choice of this property for our recent getaway. Our group, comprised of two families totaling eight people—four adults and four kids—found the accommodations to be precisely as described. The home is simply stunning, boasting an ideal location and breathtaking views that exceeded our expectations. Every detail of our stay was attended to, ensuring our comfort and convenience. Matt, our gracious host, was exceptionally responsive and went above and...
New Construction Timber Frame / Mins to mountain and restaurants / Amazing views

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

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

Country house minutes from Killington and Okemo

10.0 out of 10, Exceptional, (5)
"Our family loved this wonderful home. Even more perfect than the pictures! The house is so cozy and the expansive layout enabled the grownups to enjoy the game room, fireplace, and hot tub while the kiddos napped. Marielba and her family are the best hosts we have ever stayed with - so thoughtful and communicative. We felt not simply welcomed, but cared for. We stayed for 10 days to ski at Killington/Pico and Okemo, each just minutes away. And we loved exploring picturesque Woodstock. We...
Country house minutes from Killington and Okemo

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

8.0 out of 10, Very Good, (1)
"We had three adults and three kids stay and had a great time. The facilities were very clean and neat and all the appliances worked well. Plenty of room to stretch out and relax after skiing at Okemo. There was no cellphone service for Verizon at the cabin and we had to ask for the WIFI password. Bedding was awesome as were sheets and towels. All the TVs worked well. Would stay there again. Management was quick to answer our questions."
The Whimsical Chalet is a lovely cape on acres. Private setting less than 10 minutes to skiing.
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

3.0 star property
9.0 out of 10, Wonderful, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is AED 1,939
AED 2,618 total
includes taxes & fees
10 Jan - 11 January 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (222)
"We had the best time at Jeff’s perfect cozy ‘little loft’! It exceeded expectations! We especially enjoyed the hot tub after long days of skiing!"
Cozy Loft for two with Hot Tub

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (178)
"We had a lovely time, and Dan was very accommodating, especially when we had to delay our trip by a day due to a snow storm!"
The price is AED 514
AED 658 total
includes taxes & fees
6 Jan - 7 January 2025
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.