Photo by Robbie Martin

Search Chalets in Upton

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 49 Chalets in Upton with updated reviews, rates, and availability.

New Built! 2025 Cozy 3-bedroom chalet with water access to Rangeley Lake

10.0 out of 10, Exceptional, (1)
"My wife and I had a fantastic stay. The house was perfect for us in every way. It was very comfortable, cozy and as clean as they come. Mark was easy to deal with and very responsive to questions prior to booking. The location was perfect. It is close to town and just far enough away for some peace and quiet. We will definitely be booking here again. "
New Built! 2025 Cozy 3-bedroom chalet with water access to Rangeley Lake

Sunday River less than 1 mile! Hot Tub! Fire Pit! Sleeps 10!

10.0 out of 10, Exceptional, (6)
"Amazing spot with lots of bed space and a hot tub :) highly recommend for a group ski trip! Nate was also super communicative and helpful!"
The price is AED 992
AED 2,378 total
includes taxes & fees
8 Jun - 9 Jun
Sunday River less than 1 mile! Hot Tub! Fire Pit! Sleeps 10!

Panoramic mountain view/Hot Tub/Shuffleboard/Theater room Sunday River

9.6 out of 10, Exceptional, (10)
"We absolutely loved this house! It's very clean and has everything needed inside. We loved the proximity to Sunday River and all the fun activities in the game room for the kids! Hot tub was a hit too!!!"
Panoramic mountain view/Hot Tub/Shuffleboard/Theater room Sunday River

Summer special!!! Golf, hiking, kayak and paddle board, fish and swim!

9.8 out of 10, Exceptional, (21)
"Great property, very clean and spacious! We will be back!"
Summer special!!! Golf, hiking, kayak and paddle board, fish and swim!

Brand New. Views! Hot Tub. Sleeps 14. Kid Friendly

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a lovely stay in this beautiful house! The host ensured that we had all we needed for a wonderful visit. Very well equipped, comfortable furniture and beds, first class all the way."
The price is AED 1,120
AED 2,999 total
includes taxes & fees
8 Jun - 9 Jun
Brand New. Views! Hot Tub. Sleeps 14. Kid Friendly

The Lone Star- Hot Tub, AC, Pool Table

10.0 out of 10, Exceptional, (11)
"We loved the Lone Star for our 3 night ski weekend with our adult children and spouses. The house was so cozy and comfortable. The 3 bedrooms were roomy and bright. The kitchen and living room had beautiful views of the mountain and we could see fireworks Saturday night from the front deck. The downstairs was the perfect place to unwind and play some games after dinner."
The Lone Star- Hot Tub, AC, Pool Table

Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

10.0 out of 10, Exceptional, (119)
"Nice comfortable stay near Sunday River. Worked great for two families staying for the weekend. "
Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

Sunday River, sleeps 14, gym, chefs' kitchen, hot tub, game room, firepit, AC

10.0 out of 10, Exceptional, (6)
"Impressive home with all you need and then some! Great location near Sunday River Mtn. New home in a new development with lots of high end appliances throughout the home, making our stay very comfortable. Would love to stay again "
Sunday River, sleeps 14, gym, chefs' kitchen, hot tub, game room, firepit, AC

2 miles within Sunday river, mountain side house

9.6 out of 10, Exceptional, (33)
"Great place, great location to see fireworks on NYE at Sunday River and easy drive to and from the mountain. Perfect place for our group!"
2 miles within Sunday river, mountain side house

NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

10.0 out of 10, Exceptional, (9)
"Great location, great amenities "
NEW Chalet 6 minutes from Sunday River! Hot tub, Sauna, Sleeps 12, Dog Friendly!

Hike, fish, bike, float the river, explore or just relax...

9.6 out of 10, Exceptional, (19)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: House was located minutes from the mountain, which we really appreciated. We stayed here with three families, and there was plenty of space for all."
Hike, fish, bike, float the river, explore or just relax...

Chalet with new Hot Tub, 3 min to Sunday River ski lifts!

9.6 out of 10, Exceptional, (26)
"We had a wonderful time on our quick trip up to Sunday River. This place is so close! The hot tub after a long day on the slopes was perfect! We also got to bring along our pup and she was comfortable during her stay as well! We had a great time! "
The price is AED 837
AED 1,757 total
includes taxes & fees
15 Jun - 16 Jun
Chalet with new Hot Tub, 3 min to Sunday River ski lifts!

2 miles to Sunday River! Plus, golf, hike, bike, swim, fish and float!

10.0 out of 10, Exceptional, (75)
"This is the second time I’ve stayed at this house. It is fabulous for our skiing group. The house and the hot tub are immaculate and access to property management, and the owners was immediate with answers to any questions that we had. "
2 miles to Sunday River! Plus, golf, hike, bike, swim, fish and float!

Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

10.0 out of 10, Exceptional, (7)
"We stayed over there for three night over Xmas holidays. The property is very organized and beautiful. The kitchen is equipped very well. The beds are very nice and comfy. Great location, it’s right near Sunday River ski resort."
Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

Log Cabin on 6 acres w/direct ATV trail access, SouthWest Mountain views/sunsets

10.0 out of 10, Exceptional, (16)
"I stayed here with a group for a weekend of ATVing and we all really enjoyed the property and we will be coming back again."
Log Cabin on 6 acres w/direct ATV trail access, SouthWest Mountain views/sunsets

Heated Pool, Pet friendly, mins to SR Golf Course

10.0 out of 10, Exceptional, (2)
"Fantastic mountain getaway. Everything was new and comfortable. Owners brought us a brand new iron because we had a wedding to attend. Top notch!! "
Heated Pool, Pet friendly, mins to SR Golf Course

Mountainside Chalet direct views of Sunday River

9.2 out of 10, Wonderful, (34)
"Great location to stay with your family. We enjoyed a few nights of games, home cooking, hiking & skiing. "
Mountainside Chalet direct views of Sunday River

Cozy Cabin Getaway North of White Mountains

10.0 out of 10, Exceptional, (22)
"We had a lovely few days up in the mountains! "
Cozy Cabin Getaway North of White Mountains

Lake front house in Bethel Maine

9.6 out of 10, Exceptional, (32)
"This property is absolutely beautiful, immaculate and well equipped. We enjoyed the house, the lake and Bethel. We hope to return next summer."
Lake front house in Bethel Maine

New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk Room

10.0 out of 10, Exceptional, (4)
"My group and I had such a great weekend staying at Hazy Bear! The house was cozy, beautiful, and so relaxing. Being close to Sunday River resort was also a plus. Stephen was very friendly, and made sure our stay was perfect! I would definitely come back for another cabin trip here! "
The price is AED 802
AED 2,804 total
includes taxes & fees
16 Jun - 17 Jun
New.Minutes from Slopes.Firepit.2-Fireplaces.Hot Tub.Sauna.Rec Room.Bunk 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.
Save an average of 15% on thousands of hotels when you're signed in