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Featured Chalets in Simpson and around

⛷️Community Ski Hill! Stay warm with us by the fireplace at Willow’s Place! ⛷️🔥
Property grounds

⛷️Community Ski Hill! Stay warm with us by the fireplace at Willow’s Place! ⛷️🔥

10.0 out of 10, Exceptional, (25)
"Our stay was everything i imagined. The house was beautiful and accommodations were impeccable. The host was available it seemed 24/7 with kindness and patience. Looking forward to booking again for the spring summer months. "
⛷️Community Ski Hill! Stay warm with us by the fireplace at Willow’s Place! ⛷️🔥
Lake Wallenpaupack, Poconos Hilltop Haven with children’s playarea and 5 kayaks!
Property grounds

Lake Wallenpaupack, Poconos Hilltop Haven with children’s playarea and 5 kayaks!

10.0 out of 10, Exceptional, (25)
"This vrbo was the most well appointed one I have ever stayed in. They had everything you could need in the kitchen and an incredible amount of toys for the children to play with. "
Lake Wallenpaupack, Poconos Hilltop Haven with children’s playarea and 5 kayaks!
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
Exterior

Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.

9.6 out of 10, Exceptional, (106)
"My husband and I stayed for our anniversary week in early September and the place could not have been more perfect! The photos in the listening don't do the property justice. The lake was spectacular. Perfect location with rustic cabin charm!"
Experience Lakefront bliss! 3 bedroom chalet near Elk Mountain Ski Area.
★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
Property grounds

★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!

9.8 out of 10, Exceptional, (282)
"The property was amazing! Not only did it have everything we were looking for but the location was perfect! We even got to meet and feed the deer. It was truly amazing and planning on staying here again!!!"
The price is €484
includes taxes & fees
9 Jan - 10 Jan 2025
★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
Adorable lake home with 2 bedrooms and sleep in loft with full size beds
Beach nearby

Adorable lake home with 2 bedrooms and sleep in loft with full size beds

10.0 out of 10, Exceptional, (47)
"Adorable cabin , very clean , cozy, Nice area! We had everything we needed. You will need to bring your own sheets and towels. WiFi was fast."
Adorable lake home with 2 bedrooms and sleep in loft with full size beds
Lakefront Cabin with Fantastic views & Private Dock, The Hideout!!
Property grounds

Lakefront Cabin with Fantastic views & Private Dock, The Hideout!!

10.0 out of 10, Exceptional, (12)
"Eight family members stayed for a week in this lovely home. It was well stocked with all the supplies that we needed. We particularly enjoyed the use of the canoe, water boards, and tubes during our stay. During the week we all enjoyed the many facilities of the Hideout."
Lakefront Cabin with Fantastic views & Private Dock, The Hideout!!
Spacious 5 BR/3 BA Pocono Chalet game room in the Hideout
Exterior

Spacious 5 BR/3 BA Pocono Chalet game room in the Hideout

9.4 out of 10, Exceptional, (44)
"The house was nice. It wasn't quite as secluded as we had expected. Getting checked into the gated community took some time as there was a long line of people waiting to register. The property manager was very helpful and quick to get back to us."
Spacious 5 BR/3 BA Pocono Chalet game room in the Hideout
Lakefront on Wallenpaupack with Hot Tub - Pet Friendly
Outdoor dining

Lakefront on Wallenpaupack with Hot Tub - Pet Friendly

9.4 out of 10, Exceptional, (64)
"We had such a beautiful weekend with family at this property! We took full advantage of all amenities provided including the hot tub and kayaks. The property was clean and spacious and we would love to visit again! "
Lakefront on Wallenpaupack with Hot Tub - Pet Friendly
Ski ELK • Lakeview• HotTub• Movie Theater• Games• Pool Seasonal
Interior

Ski ELK • Lakeview• HotTub• Movie Theater• Games• Pool Seasonal

10.0 out of 10, Exceptional, (7)
"The property was clean, well maintained. Hot tub was great. Very spacious. Great scenery. Host promptly answered questions. Would definitely book again. "
Ski ELK • Lakeview• HotTub• Movie Theater• Games• Pool Seasonal
Briar Hill North Lakefront Contemporary with Private Dock
Exterior

Briar Hill North Lakefront Contemporary with Private Dock

9.2 out of 10, Wonderful, (50)
"Beautiful house, plenty of room, comfortable and perfect spot on the lake ."
Briar Hill North Lakefront Contemporary with Private Dock
Pocono Chalet- walking distance to Lake Wallenpaupack- 3 Full baths
Exterior

Pocono Chalet- walking distance to Lake Wallenpaupack- 3 Full baths

10.0 out of 10, Exceptional, (3)
"This house is such a good use of space! We were a family of 8 and we fit perfect and even had an extra bed. The central space is nice to gather and the deck was lovely. This was a quick walk to the water and central to everything we wanted to do in the area. Heather was super responsive and wonderful to work with! We would absolutely stay again and recommend the property. "
Pocono Chalet- walking distance to Lake Wallenpaupack- 3 Full baths
Cozy Cedar Chalet with Heated Pool
Smart TV, fireplace, video games, books

Cozy Cedar Chalet with Heated Pool

10.0 out of 10, Exceptional, (9)
"I selected the home because it was close to Lake Winola, where we had our high school class reunion. The house was immaculate and had many areas where we could sit and catch up. Although the weather didn't cooperate, we were able to take a dip in the beautiful pool. We would definitely book there again."
Cozy Cedar Chalet with Heated Pool
Cozy chalet-style home with fire pit in The Hideout, a five star community.
Fridge, microwave, oven, stovetop

Cozy chalet-style home with fire pit in The Hideout, a five star community.

10.0 out of 10, Exceptional, (6)
"We enjoyed our stay. House is very well kept and its a very peaceful place to spend some quiet time."
Cozy chalet-style home with fire pit in The Hideout, a five star community.
Walk to Beach, Spacious Backyard
Outdoor dining

Walk to Beach, Spacious Backyard

8.6 out of 10, Excellent, (4)
"House was perfect for what we needed. Traveled with two toddlers and grandparents. Tons of games to choose from to keep you occupied when not at the beach. House in a community that had beaches and pools. So easy to enjoy your time"
Walk to Beach, Spacious Backyard
Lakes, Ski Hill, Golf, Game Room & Endless Foliage @ Chalet on the Green
Outdoor pool, a heated pool

Lakes, Ski Hill, Golf, Game Room & Endless Foliage @ Chalet on the Green

10.0 out of 10, Exceptional, (4)
"Great host, and great property! Our family came up from Florida to visit. Very clean, very spacious. The host was amazing and took care of everything. Everyone LOVED the place, and will definitely be staying here in the future. "
Lakes, Ski Hill, Golf, Game Room & Endless Foliage @ Chalet on the Green
Family Fun in The Poconos at The Rosewood Hideout
Outdoor dining

Family Fun in The Poconos at The Rosewood Hideout

9.8 out of 10, Exceptional, (27)
"We had a great time at the Rosewood last week. The house was very clean and spacious enough that all 9 of us had plenty of room. We especially loved the deck, fire pit and grill and used them every evening. Cathleen was very responsive with a community access issue and it was resolved very quickly. We all enjoyed our family vacation at this wonderful home."
Family Fun in The Poconos at The Rosewood Hideout
The Gray Chalet - private lot close to Lake Wallenpaupack & downtown Hawley
Interior

The Gray Chalet - private lot close to Lake Wallenpaupack & downtown Hawley

9.6 out of 10, Exceptional, (28)
"The experience was "
The Gray Chalet - private lot close to Lake Wallenpaupack & downtown Hawley
Lake Vibez Lakefront Oasis: Private Dock, Boats, Skiing &Tubing -Hideout Poconos
Fridge, microwave, oven, stovetop

Lake Vibez Lakefront Oasis: Private Dock, Boats, Skiing &Tubing -Hideout Poconos

9.8 out of 10, Exceptional, (10)
"We had an amazing stay with our family and friends with enough space and entertainment for all!"
Lake Vibez Lakefront Oasis: Private Dock, Boats, Skiing &Tubing -Hideout Poconos
Chalet Log Home in Lake Ariel Hideout community
Exterior detail

Chalet Log Home in Lake Ariel Hideout community

10.0 out of 10, Exceptional, (4)
"Beautiful and very clean property! Great location in a safe community with plenty of things to do! About 20 minute drive to local attractions and shopping. My family enjoyed staying and we will likely return! Only tip is to bring your own shower soaps- everything else is well provided! Thank you for sharing your lovely home!"
Chalet Log Home in Lake Ariel Hideout community
The All Season Retreat!
Private kitchen

The All Season Retreat!

9.0 out of 10, Wonderful, (4)
"Good"
The All Season Retreat!
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 Simpson

★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
Property grounds

★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!

9.8 out of 10, Exceptional, (282)
"The property was amazing! Not only did it have everything we were looking for but the location was perfect! We even got to meet and feed the deer. It was truly amazing and planning on staying here again!!!"
The price is €484
includes taxes & fees
9 Jan - 10 Jan 2025
★★★★★ Luxury Waterfront: Hot Tub, Fireplace, Kayaks, XBOX Game Pass, 100mb WiFi!
Elk Mountain Ski Resort: Rustic Home on 21 Acres
Fridge, microwave, oven, stovetop

Elk Mountain Ski Resort: Rustic Home on 21 Acres

9.8 out of 10, Exceptional, (35)
"I’ve stayed at many places. Let me tell you this is at the top of the list. The house is beautiful, clean (top to bottom) and the location and views are breathtaking. The house has everything you need on site and in kitchen etc. We absolutely loved the place and my teenage boys are already asking when we’re going back Again overall an amazing place and we”ll definitely be booking again !!!"
Elk Mountain Ski Resort: Rustic Home on 21 Acres
Wally’s Cottage|New|HotTub|Fireplace|Close to Town
Exterior

Wally’s Cottage|New|HotTub|Fireplace|Close to Town

10.0 out of 10, Exceptional, (32)
"Everything was great, house was very clean and very nice. Owners were very nice and helpful with questions. "
The price is €396
includes taxes & fees
29 Dec - 30 Dec
Wally’s Cottage|New|HotTub|Fireplace|Close to Town
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.