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Compare 59 Chalets in Olean with updated reviews, rates, and availability.

New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥

10.0 out of 10, Exceptional, (31)
"Everything was amazing! Loved our time together here. "
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥

All-Season ski chalet in Ellicottville, NY, outdoor hot tub with stunning views!

9.8 out of 10, Exceptional, (234)
"Although I was a little anxious for the check-in data, it came with plenty of time to check in. The property owner obviously cares to provide a great experience while staying at the Rooster's Den. Everything was just as advertised-this property is large, comfortable and well maintained. I would definitely stay at the Rooster's Den again."
All-Season ski chalet in Ellicottville, NY, outdoor hot tub with stunning views!

3-bedroom chalet with Slopes View in Ellicottville

9.0 out of 10, Wonderful, (2)
"It was a nice location, only real issue was not having proper pans for cooking breakfast. It also would have been nice to have a fire, and use of the hot tub. The house was clean, and cozy. Great communication along the way with the host though. "
3-bedroom chalet with Slopes View in Ellicottville

Hidden Gem💎Large Ellicottville Chalet🍁Woods⛷ Hot Tub 🕹️ Arcade Fun 🔥Fire Pit

10.0 out of 10, Exceptional, (16)
"We had our annual retreat at the house — it slept 19 comfortably. The huge table is great for games, and the open floor plan is great for a big group. The bears and other stuffed heads add some flavor, for sure. We loved the foosball and hockey and video games downstairs, and the hot tub was great after skiing Holiday Valley. We would definitely do it again! "
Hidden Gem💎Large Ellicottville Chalet🍁Woods⛷ Hot Tub 🕹️ Arcade Fun 🔥Fire Pit

5-Bed Chalet -Stunning Fall & Winter Views - Cozy Retreat

9.0 out of 10, Wonderful, (2)
"Setup of the house was fantastic for our family. Having two separate levels to spreadout was helpful. The huge family room was a big bonus "
5-Bed Chalet -Stunning Fall & Winter Views - Cozy Retreat

Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

10.0 out of 10, Exceptional, (1)
"Great place, super friendly with awesome communication, thank you! "
The price is AED 477
AED 775 total
includes taxes & fees
5 Feb - 6 Feb
Timberline Lodge - Ski Wing - Charming chalet in downtown Ellicottville

NEW! -- Walk to Village!👍 Stunning timber chalet!👌 Hot-Tub, Bonfire🔥& more!

9.8 out of 10, Exceptional, (6)
"After a mere 16 years, I finally convinced family to come up for the Fall Fest festivities and this house was the cherry on top. It is in a great location to the main hub of Ellicottville, easy walking distance or a super cheap Uber ride. Even to Holiday Valley, the walk is super doable. The house was big enough with extra room for 12 adults and a dog. While the open concept is awesome for the views, it is a little loud for anyone sleeping on the second floor. But that wouldn’t deter me from...
NEW! -- Walk to Village!👍 Stunning timber chalet!👌 Hot-Tub, Bonfire🔥& more!

★ Private Hideaway w/Hot Tub - Stylish & Serene w/ Wood Burning Fireplace ★

10.0 out of 10, Exceptional, (14)
"Amazing place nestled in the wood. "
★ Private Hideaway w/Hot Tub - Stylish & Serene w/ Wood Burning Fireplace ★

Best of both worlds; chalet located on a private lot in the pines and only 1 miles from the village!

10.0 out of 10, Exceptional, (26)
"This property was absolutely perfect for our family. It had every amenity we could have possibly needed. The layout of the house was great. Plenty of common area for our group of 7 kids and 9 adults to spread out. The rooms were great with a mix of some upstairs and downstairs, some bunk rooms for the kids and regular rooms for the adults. Plenty of bathrooms. For the first time ever, our entire family was able to sit down together all at one table to enjoy Christmas dinner together. The owners...
Best of both worlds; chalet located on a private lot in the pines and only 1 miles from the village!

UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome

10.0 out of 10, Exceptional, (58)
"This was our second time at Yves' awesome log cabin. We had a very comfortable stay again--thank you!"
The price is AED 1,432
AED 2,444 total
includes taxes & fees
2 Mar - 3 Mar
UNIQUE Log Style Cozy Ski Chalet - Walking Distance To Town - Pets Welcome

Beautiful chalet on 5 acres - 2 min to Village!👌 Hot-Tub, Sauna, Fire Pit🔥

10.0 out of 10, Exceptional, (45)
"The house is great. No problems whatsoever. Would definitely stay here again. Thank you."
Beautiful chalet on 5 acres - 2 min to Village!👌 Hot-Tub, Sauna, Fire Pit🔥

New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥

10.0 out of 10, Exceptional, (51)
"The chalet was everything we hoped for. Very accurate listing, beautiful location, and excellent communication with owners. Would book again!"
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥

Spacious 8 Bdrm Chalet set up for entertaining!

10.0 out of 10, Exceptional, (5)
"Our family of 16 spent our Christmas here and it was one of best celebrations. The cabin was perfect, and we had plenty of room to spread out."
Spacious 8 Bdrm Chalet set up for entertaining!

A+ Secluded Beauty w/Hot Tub, Firepit, Bar, Privacy & Views🔥

9.8 out of 10, Exceptional, (6)
"This is our second time staying at a “Stay Aprés” property, but the first time at this particular spot. We were so impressed with the initial stay that we couldn’t wait to book another trip a month later, and this location was just as impressive if not more.Location:Less than 5 mins from the main road in town and the mountains (perfect for the family members that went snowboarding but also great for the ones who wanted to stay behind at the house all weekend).Amenities:Hot tub is incredible, and...
A+ Secluded Beauty w/Hot Tub, Firepit, Bar, Privacy & Views🔥

Ellicottville Chalet & Cottage 5 Mi to Village

Ellicottville Chalet & Cottage 5 Mi to Village

Ellicottville Treetop Retreat: All seasons Ellicottville Chalet

10.0 out of 10, Exceptional, (6)
"Our stay at this VRBO property was truly exceptional, set against a breathtaking winter backdrop that made for a perfect getaway. The owners were outstanding communicators, providing us with all the necessary details well in advance, which made our arrival seamless and stress-free. The house itself is incredibly spacious, comfortably accommodating six adults and eight children. It was thoughtfully designed with ample room for everyone to spread out, yet still felt intimate and cozy. Beautifully...
Ellicottville Treetop Retreat: All seasons Ellicottville Chalet

Luxurious Chalet! Hot-tub, Bonfire & A+ Location for Skiing/Town

10.0 out of 10, Exceptional, (30)
"We hosted three families at the house and had plenty of room for everyone! The host was easy to reach and helpful in multiple situations. We cooked at the house over the holiday and noticed that this kitchen was fully stocked with spices and supplies, above all other rentals we’ve used in the past. Beautiful views from the house and a great experience."
Luxurious Chalet! Hot-tub, Bonfire & A+ Location for Skiing/Town

EVL House w/ Pool & Hot Tub, 7 mins to Holiday!

9.0 out of 10, Wonderful, (10)
"The property was exactly large enough to fit our group."
EVL House w/ Pool & Hot Tub, 7 mins to Holiday!

Ellicottville Chalet 3 Miles From Village on a secluded lot w/pond

8.0 out of 10, Very Good, (2)
"We all came up to see the eclipse. The cottage was easy to fine, had great bedrooms, a wonderful kitchen, and perfecct yard for all my grandchildren to enjoy. Our host was helpful and easy to contact for questions. We do recommend this "House by a pond" for a pleasant stay away from home."
Ellicottville Chalet 3 Miles From Village on a secluded lot w/pond

The Pines on Maples~ Hot Tub ~ Fire Pit & Indoor Fireplace - Game Room

9.8 out of 10, Exceptional, (9)
"Gorgeous woodland chalet with all the comforts for our New Year’s ski trip. Loved the hot tub, wood burning fireplace, and comfortable beds for our 4 adults. Excellent heating on all 3 floors, perfect for apres-ski dinners and breakfast in the cozy kitchen and dining area. Great job plowing the driveway each morning as we enjoyed fresh powder skiing only minutes away. Five Stars! "
The price is AED 2,387
AED 3,500 total
includes taxes & fees
2 Mar - 3 Mar
The Pines on Maples~ Hot Tub ~ Fire Pit & Indoor Fireplace - Game Room
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 Olean

Cozy Country Get Away Suite with a view of the Enchanted Mountains

10.0 out of 10, Exceptional, (11)
"great little getaway, very beautiful places around to drive to!"
The price is AED 327
AED 524 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Country Get Away Suite with a view of the Enchanted Mountains

Location! Holiday Valley. Great Hill View & Includes Ski Locker in Main Lodge!

9.8 out of 10, Exceptional, (46)
"We had the best stay, great location - close to the slopes. The property was clean and cozy. Cheryl was very thoughtful and accommodating throughout our trip. We would definitely stay here again!"
Location! Holiday Valley. Great Hill View & Includes Ski Locker in Main Lodge!

New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥

10.0 out of 10, Exceptional, (31)
"Everything was amazing! Loved our time together here. "
New & Stunning Chalet!⛷ A+ Reno, Hot-Tub, Barrel Sauna, Slope Views, Fire Pit🔥
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.