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Compare 379 Vacation Homes in Upton with updated reviews, rates, and availability.

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space
Privacy ensured on 86acres with an indoor pool less than 15minutes to SR base

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (40)
"Absolutely amazing property! The hosts are gracious and very quick to reply to you. Will definitely be back!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space
Lakeview Retreat with Game Room, Beach, and Spectacular Views
Exterior

Lakeview Retreat with Game Room, Beach, and Spectacular Views

Lakeview Retreat with Game Room, Beach, and Spectacular Views
The Mansion- Exclusive Private Estate on 5 Pristine Acres
Exterior

The Mansion- Exclusive Private Estate on 5 Pristine Acres

10.0 out of 10, Exceptional, (33)
"The house was AMAZING! Had a wonderful time We had a pretty big group and the house was comfortable enough for all of us including kids and a dog. Did not feel crowded at all. Hosts were wonderful, very accommodating with late check out and asking if we need anything. The views from the house are spectacular, you dont need to go out at all honestly, you would have a good time just enjoying the house amenities and the views, def worth the drive from NY"
The Mansion- Exclusive Private Estate on 5 Pristine Acres
Mainestay | 4 Bed, 2 Bath
Living area

Mainestay | 4 Bed, 2 Bath

9.8 out of 10, Exceptional, (20)
"Great stay, house was clean upon arrival and had plenty of extras to make for a fun long weekend up near Sunday River. Will definitely come again."
Mainestay | 4 Bed, 2 Bath
RANGLEY LAKE WATERFRONT!!! Sleeps 11
Outdoor dining

RANGLEY LAKE WATERFRONT!!! Sleeps 11

9.8 out of 10, Exceptional, (106)
"Had a great weekend get away, good location and very nice place "
RANGLEY LAKE WATERFRONT!!! Sleeps 11
Brookside II B-302 | 1 Bed, 1 Bath
updated unit with new furnishings

Brookside II B-302 | 1 Bed, 1 Bath

10.0 out of 10, Exceptional, (3)
"Very clean and functional space. Great access to amenities and ski on/off. Good amount of space for two adults. Would recommend and would stay again. Thanks for a great stay!"
Brookside II B-302 | 1 Bed, 1 Bath
South Ridge G-01 | 3 Bed, 2 Bath
Kitchen area with seating for two

South Ridge G-01 | 3 Bed, 2 Bath

South Ridge G-01 | 3 Bed, 2 Bath
New Luxury w/ HotTub, Sauna, GameRoom,5mintoSlopes
Ample room for the whole family outside to enjoy the mountains

New Luxury w/ HotTub, Sauna, GameRoom,5mintoSlopes

10.0 out of 10, Exceptional, (6)
"We stayed for three nights - our group was moms and tween/teen daughters. The house is brand new and in immaculate condition. Everything was clean and we loved all the extra small touches the hosts have provided!"
New Luxury w/ HotTub, Sauna, GameRoom,5mintoSlopes
Rangeley Getaway
Exterior

Rangeley Getaway

"Great spot. Great house. Super clean!"
Rangeley Getaway
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
Pool

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (26)
"Fun"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
90 Second, Traffic-Free Drive to Sunday River
Living area

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (13)
"A lovely clean place that would be wonderful for families with children! We couldn’t be closer to Sunday River!!"
90 Second, Traffic-Free Drive to Sunday River
🐾Gray Wulff - This rustic dog friendly camp sits on the shore of Quimby Pond

🐾Gray Wulff - This rustic dog friendly camp sits on the shore of Quimby Pond

9.6 out of 10, Exceptional, (19)
"It was a delightful 3 days of fly fishing and woodland solitude."
🐾Gray Wulff - This rustic dog friendly camp sits on the shore of Quimby Pond
JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.
Exterior detail

JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.

9.8 out of 10, Exceptional, (125)
"Family reunion location with plenty of space! Great hot tub and amenities!"
JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.
Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

8.4 out of 10, Very Good, (49)
"Great location and nice place."
Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi
River Valley Acres | 4 Bed, 3.5 Bath
Great room

River Valley Acres | 4 Bed, 3.5 Bath

10.0 out of 10, Exceptional, (8)
"Clean and spacious"
River Valley Acres | 4 Bed, 3.5 Bath
Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise
Property grounds

Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise

10.0 out of 10, Exceptional, (17)
"Excellent location for quiet get away. Golf course was in walking distance as well as the lake dock. The deer were everywhere and walked through the backyard. While we hoped to see a moose we didn’t but the conditions were excellent in the area. Enjoyed our stay!"
Rangeley Lake House with lake access, Saddleback 15min, outdoor paradise
🐾As Good As It Gets - Private location on Dodge Pond, dog friendly
Welcome to As Good As It Gets

🐾As Good As It Gets - Private location on Dodge Pond, dog friendly

9.4 out of 10, Exceptional, (20)
"We had a terrific weekend of fishing and sightseeing. Lovely property with a great view."
🐾As Good As It Gets - Private location on Dodge Pond, dog friendly
Luxurious Ski-in/ski-out Sunny Sunday River Townhouse
Club house with stove TV, saline pool, hot tub and sauna just steps away.

Luxurious Ski-in/ski-out Sunny Sunday River Townhouse

10.0 out of 10, Exceptional, (63)
"Great spot with ski in / ski out access."
Luxurious Ski-in/ski-out Sunny Sunday River Townhouse
Powder Ridge Townhouse 33 | 3 Bed, 2.5 Bath
Open concept living space

Powder Ridge Townhouse 33 | 3 Bed, 2.5 Bath

9.8 out of 10, Exceptional, (6)
"Nice place for a group of 4. Skiing at Sunday River is close by. Kitchen is well equipped."
Powder Ridge Townhouse 33 | 3 Bed, 2.5 Bath
Relaxing cabin in the mountains...Snowmobile, ATV, Fish, Hike, Relax
Exterior

Relaxing cabin in the mountains...Snowmobile, ATV, Fish, Hike, Relax

10.0 out of 10, Exceptional, (5)
"This property was so relaxing and peaceful it made our short weekend getaway so relaxing it felt like it was longer"
Relaxing cabin in the mountains...Snowmobile, ATV, Fish, Hike, Relax
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 Upton

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space
Privacy ensured on 86acres with an indoor pool less than 15minutes to SR base

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (40)
"Absolutely amazing property! The hosts are gracious and very quick to reply to you. Will definitely be back!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
Pool

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (26)
"Fun"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room
Peaceful Lakefront Cabin w/ amazing views and sauna; minutes to skiing
What an incredible view from the deck!

Peaceful Lakefront Cabin w/ amazing views and sauna; minutes to skiing

10.0 out of 10, Exceptional, (16)
"Had such an amazing and relaxing time here. The property is beautiful and the sauna is an added plus!"
Peaceful Lakefront Cabin w/ amazing views and sauna; 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.