Chalet holiday rentals in Owls Head

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Top-rated chalet rentals in Owls Head

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Top Guest favourite

The exterior of the Deer Pine Chalet is shown from above, displaying a custom log home surrounded by trees. A large deck features comfortable seating, and a well-kept lawn leads to a private driveway, completing the serene woodland setting.

Chalet in Jay

4.95 out of 5 average rating, 141 reviews

Ski Whiteface - Luxury, Sauna, Hot Tub

The Deer Pine Chalet is a custom built real log home in the Adirondack Park. This winter wonderland getaway is just 12.5 miles away from Whiteface Mountain boasting 22 miles of ski and snowboard trails. Our neighborhood has 6 cross-country skiing, snowshoeing and hiking trails with a combined 10 miles; all trails intersect with a trail entrance steps from the chalet! You can go ice skating, use toboggan chute or dog sledding in the historic town of Lake Placid just 21 miles away from the chalet.

Top Guest favourite

A spacious great room is highlighted by large windows, allowing natural light to fill the space. A stone fireplace anchors the room, surrounded by wood paneling. A large leather sectional sofa offers seating, with a wooden platform and television visible in the background.

Chalet in Jay

4.97 out of 5 average rating, 119 reviews

Doe - A- Deer

Welcome to Doe-A-Deer Lodge in Jay NY ! Come and stay in this beautiful 6 bedroom 3 bathroom knotty pine home in the Adirondacks! After a day of exploring, come home to this peaceful retreat and relax in the amazing two-story great room with radiant floor heat below your feet! We have updated with brand new stainless steel appliances, granite countertops, tile floor, carpet, a large leather sectional, and a flat screen TV! We've got it all-WiFi, cable, games, and more! Private setting too!

Top Guest favourite

A charming chalet is nestled among lush greenery, framed by tall trees. The sloped roof and wooden balcony create a rustic appeal. A well-maintained gravel path leads to the entrance, inviting guests into a serene woodland setting.

Chalet in Jay

4.92 out of 5 average rating, 138 reviews

Camp Red Fox - 15 min from whiteface, wood stove

Enjoy all that the High Peaks region has to offer in our cozy chalet. Camp Red Fox comfortably sleeps 2 adults and 2 kids with king size and low bunk beds. Warm up by the wood stove in the winter and stay cool with AC in the summer. Enjoy darts, vinyl, or a movie night in the den. The kitchen is well equipped. Less than 20 minutes to Whiteface Mountain and 30 minutes to Lake Placid. Minutes away from hiking, swimming, and cross country ski trails. High speed internet with Roku stick and cable.

Top Guest favourite

A rustic wooden cabin is set within a picturesque landscape, surrounded by trees and open space. A large deck extends from the structure, and a fire pit is visible on the grassy yard, accompanied by a parked boat. Nearby, two propane tanks are positioned next to the cabin.

Chalet in Bloomingdale

4.98 out of 5 average rating, 133 reviews

McKenzie Mtn Way Chalet

Beautiful location in Bloomingdale with views of Whiteface Mtn and the McKenzie Mtn Range. You and your family and friends can enjoy the secludedness from your busy lives while sitting next to a campfire in the large fire pit in the yard. Located only 10 min from Saranac Lake, 20 min to Lake Placid, and 30 min to Whiteface Mtn., our home offers many close by outdoor activities and experiences (hiking, biking, boating, swimming, downhill and x-country skiing, skating, sledding, dog sleds, etc)

Top Guest favourite

An A-frame chalet is surrounded by lush greenery, featuring large front windows that invite natural light. A wooden deck extends from the entrance, with comfortable outdoor seating visible. The structure's triangular shape and earthy colors blend harmoniously with the wooded landscape.

Chalet in Wilmington

4.95 out of 5 average rating, 228 reviews

Little Peak Chalet - Cozy A-Frame, Whiteface Mt

Little Peak Chalet is a cozy A-frame tucked into the wooded slopes of Juniper Hill in Wilmington, NY. This peaceful hideaway offers stunning views of Whiteface Mountain, beautifully framed by the surrounding pines. Enjoy coffee on the deck, grill at sunset, or unwind by the fire pit under the stars—Little Peak Chalet is all about slowing down and connecting with nature and each other. Ideal for couples, friends, or small families seeking a scenic escape with easy access to outdoor adventures.

Top Guest favourite

An aerial view of a charming chalet surrounded by lush greenery. A spacious wrap-around deck features outdoor seating and a red umbrella, offering a cozy area for relaxation. Sunlight filters through the trees, enhancing the natural setting.

Chalet in Jay

4.96 out of 5 average rating, 247 reviews

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is Satellite TV and wifi. There is good cell coverage. World Class Fishing, Ausable Rivers are close

Top Guest favourite

A living room features a rustic wooden sofa with plush cushions, placed in front of a stone fireplace. Large windows allow natural light to fill the space, revealing wood-paneled walls and a cozy atmosphere. A patterned throw adds a pop of color to the seating area.

Chalet in Jay

4.97 out of 5 average rating, 172 reviews

Edin's Chalet Adirondacks-Whiteface 4 Beds-2 Baths

Bring the whole family to this great place with lots of room for fun. *** Ground level offers spacious great room with living room, dinning area, eat in kitchen. full bathroom, laundromat. *** Bunk room is on ground floor with 4 full beds and huge closet. *** Loft or 2nd floor has 2 bedrooms. *** One of the bedrooms is Master and it has full bathroom with standing shower, walk in closet and deck with seating area. *** Basement bedroom has queen size bed, large full size window.

Guest favourite

A spacious living area features wooden paneling and vaulted ceilings, creating a warm environment. Two comfortable sofas are positioned near a large picture window, offering views of the outdoors. A television is placed on a wooden stand, with decorative artwork enhancing the space.

Chalet in Saranac Lake

4.91 out of 5 average rating, 120 reviews

Knotty Pine Lodge

Be the first to enjoy this newly renovated air conditioned lodge. The large open plan allows your group to relax family style. The convenient location one mile from the Lake Placid side of Saranac Lake allows easy access to skiing, hiking, golf, tennis courts, snowmobiling, boating, Olympic events, exploring Lake Placid or Saranac Lake's historic community. The large decks and plentiful parking make a great spot to stay put and enjoy our space as well. Welcome to Ray Brook!

Top Guest favourite

The exterior of the cabin is surrounded by lush trees, featuring a distinctive angled roof and large windows. A deck wraps around the house, leading to a fire pit area with Adirondack chairs. A winding path connects the cabin to a nearby hammock.

Chalet in Jay

4.96 out of 5 average rating, 314 reviews

Full-body Massage Chair & Hot Tub & Wellness

🎉 Ready for a New Year Reset? 🎉 January rates are lower than usual, making it the perfect time to slow down and start 2026 with clarity at The Place of Prana. If you’re craving a calmer, more intentional start to the year, this stay is designed to help you reset your mind and body. January welcomes new rhythms, soft beginnings, and quiet evenings that make space for fresh energy. Come stay, breathe, and give yourself the reset you deserve for the year ahead.

Top Guest favourite

A peaceful view of the chalet along the serene canal reflects in the calm water. Nearby, a small fishing boat and two personal watercraft are moored. Lush trees and a green shed frame the charming property, emphasizing its tranquil lakeside setting.

Chalet in Saint-Anicet

4.99 out of 5 average rating, 251 reviews

St-Anicet, happiness in simplicity

The chalet Le ptit bonheur is located on the edge of a magnificent canal giving a superb view of Lake St-François in St-Anicet. Spa year-round , fishing, 2 kayaks included, heated pool and large bay at the end of the canal with possibility of swimming. Can receive a boat. Boat and sea doo unavailable!Downhill nearby. Beach 2 minutes by boat. Perfect for a beautiful family vacation. Residential land area of 11,000 pc Free WiFi CITQ No. 303012 exp 2025-09-30

Guest favourite

A spacious living area features wooden paneling and a polished wooden floor. A comfortable green sectional couch is arranged around a round coffee table, with a blue recliner nearby. A gas fireplace is situated against one wall, and large windows allow ample natural light.

Chalet in Jay

4.9 out of 5 average rating, 262 reviews

Adirondack Home - Cozy Mountain Hideaway

Adorable three bedrooms cedar log home on a quiet road. Take advantage of this wonderful wooded setting with hiking and XC-ski trails, tennis courts, picnic area and playground (Association amenities). Only 20 minutes drive to Whiteface Mountain Ski Resort and a scenic 30 minutes to Lake Placid (21 miles). For fishing enthusiasts, it is situated within walking distance of an Ausable River State fishing area. Neighborhood has a quiet curfew of 10pm.

Top Guest favourite

An aerial view captures the Juniper Hill A-frame nestled among a landscape blanketed in fresh snow. Surrounding evergreen trees create a serene backdrop, while the road and pathway lead away from the cozy chalet, enhancing the feeling of seclusion and tranquility.

Chalet in Wilmington

4.96 out of 5 average rating, 170 reviews

JUNIPER HILL a-frame

Juniper Hill A-frame is a newly renovated 1968 Adirondack A-frame that is loaded with character and charm. This tiny 700 square foot space is cozy and located with direct views of Whiteface Mountain. Two bedrooms/one bathroom situated on a large parcel of land complete with Christmas tree farm, fire pit, and large front deck. You won’t want to leave, but if you do, the A-frame is within walking, biking or driving distance to just about everything.