Vacation rentals in Upton

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Top-rated vacation rentals in Upton

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A private outdoor deck features a red Adirondack chair overlooking expansive green landscapes and distant mountain views. Soft lighting is provided by lanterns hanging from a sturdy wooden pergola, creating a peaceful setting for relaxation in nature.

Condo in Intervale

4.94 out of 5 average rating, 169 reviews

Upscale retreat w/ panoramic White Mountain views

ChrisRating, 5 stars6 months ago

We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

Guest favorite

A wooden dock extends into a calm lake, surrounded by lush green mountains. A boat is tied next to the dock, while a lounge chair sits invitingly on the platform. The water reflects the serene landscape, creating a peaceful atmosphere.

Cabin in Greenwood

4.92 out of 5 average rating, 13 reviews

All seasons Lake House next to ski areas

GeorgeRating, 5 stars6 months ago

Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!

Guest favorite

A fire pit surrounded by four wooden Adirondack chairs is set against a gravel area. The rustic lodge can be seen in the background, framed by trees displaying autumn colors and string lights. A peaceful and inviting outdoor space is highlighted.

Home in Jackson

4.98 out of 5 average rating, 54 reviews

The Sommet-Magical Views- Main house+Guest cottage

ChrisRating, 5 stars2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

Top guest favorite

A wooden dock extends into a calm lake, leading to a small boat anchored at the end. The water reflects a clear blue sky, with gentle ripples across the surface, and green hills visible in the distance.

Home in Harrison

5 out of 5 average rating, 6 reviews

2BR Lake House on Private Beach w/hot tub & sauna

JasonRating, 5 stars6 months ago

This is place is a gem. The lake is beautiful and the beach is very private. The house has a nice layout and is both spacious and cozy. This was our second year staying here and we plan to come back again! Dina is very responsive and great to work with.

Superhost

Chalet in Woodstock

4.82 out of 5 average rating, 11 reviews

Cozy Mountainside Retreat– come explore & Relax!

JessicaRating, 5 stars1 month ago

Nathan‘s cabin was the perfect spot for our two families to gather for a ski weekend. We had plenty of room even with four kids and it was unbelievably convenient to get to Mt. Abram! The fireplace was an added bonus in the evenings.

Superhost

A spacious living area features a large sectional sofa, a coffee table, and a flat-screen television. Natural light pours in through large windows, complemented by a skylight. A cozy fireplace is situated beside a textured black rug on the floor, adding warmth to the space.

Townhouse in Bartlett

4.85 out of 5 average rating, 105 reviews

Spacious Family Vaca Storyland*Saco*Close to all!

JoanneRating, 5 stars2 months ago

Great place to stay. The basement space for the kids is great, they each had their own bedroom but could hang in the common space. Golden Tee was a HIT! Centrally loacated to multiple ski mountains. Plenty of room to spread out and get comfortable!

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Popular amenities for Upton vacation rentals

Gym

BBQ grill

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Wifi

Air conditioning

Other great vacation rentals in Upton

Guest favorite

A wooden dock extends over a calm lake, leading to clear blue waters. Lush trees frame the background, offering a serene backdrop of nature. The smooth surface of the water reflects the blue sky and scattered clouds, creating a tranquil atmosphere.

Cabin in Stow

4.95 out of 5 average rating, 22 reviews

Large Ski Chalet Cabin on Kezar Lake

MatthewRating, 5 stars1 month ago

We had a group of 12 people and the home accommodated us very nicely. Plenty of space and amenities and very peaceful. No issues - would recommend any small or larger group to stay here. Thanks again Lori!

Top guest favorite

A covered entryway is situated beneath an upper porch, featuring a wooden bench beside a welcoming door. A stack of firewood is neatly arranged to the right, partially covered with a tarp. Soft lighting illuminates the space, accompanied by scattered autumn leaves.

Home in Greenwood

5 out of 5 average rating, 15 reviews

Cozy Greenwood Condo!

AnnieRating, 5 stars1 month ago

This condo, conveniently on the ground floor, and was clean and inviting. The wood stove provided warmth and ambiance. The furnishings included a modern well appointed coffee bar, ski themed decorations and two comfortable couches to gather around the wood stove after a day outside of adventuring. There was a mud room for outdoor clothing and boots and the bed was comfortable. The artwork in the bedroom is a fun ski-themed print. A lovely ski weekend.

Superhost

A spacious interior showcases a modern design with exposed wooden beams and large windows allowing natural light to fill the area. Glass railings overlook an open space below, creating a sense of openness and connection to the surrounding greenery.

Home in Carrabassett Valley

5 out of 5 average rating, 4 reviews

The Epic Sugarloaf Family Getaway!

KarenRating, 5 stars2 months ago

This place was very convenient to the mountain with a lift nearby and it was very clean and incredibly spacious. David is very accommodating and helpful. We sorely missed having coffee available in the morning but really that was our fault for not bringing it as it was not advertised that there would be any I just assumed for the price there would be a little coffee. Overall though great stay and very nice place - thank you!

Guest favorite

An open layout reveals warm wooden walls and high beamed ceilings in this inviting space. A dining table with white chairs sits in front of a kitchen featuring modern appliances. A comfortable seating area is visible, accentuated by a decorative rug on the warm-toned flooring.

Cabin in Eustis

4.83 out of 5 average rating, 88 reviews

Sugarloaf, Stratton, Eustis, Rangeley Rental

KateRating, 5 stars3 weeks ago

We had a wonderful weekend. It was a clean and comfortable house. We skied at sugarloaf both days and it was very convenient to the mountain. We would stay again!

Superhost

A covered porch features a comfortable seating area with a wicker sofa and matching cushions, arranged around a low coffee table. A hammock is suspended for relaxation, and a striped outdoor rug adds texture to the wooden floor. Large windows provide views of the surrounding landscape.

Home in Otisfield

4.75 out of 5 average rating, 20 reviews

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !

Guest favorite

Home in Dallas Plantation

4.93 out of 5 average rating, 29 reviews

Ski/snowmobile retreat-hot tub

HilaryRating, 5 stars2 months ago

This house is OUTSTANDING! The location is perfect, the house is spotlessly clean, top of the line kitchen. Our stay could not have been more perfect.

Guest favorite

A private pool is surrounded by a sun-soaked concrete deck, framed by lush greenery and trees. Fencing provides a safe enclosure, while picnic benches offer seating nearby. The clear water invites relaxation, set against a serene natural backdrop.

Townhouse in Bartlett

4.94 out of 5 average rating, 16 reviews

The Woodland Retreat | Spacious Family Home + Pool

BetsyRating, 5 stars2 months ago

Wonderful vacation, comfortable beds! Great clean place

Guest favorite

Cabin in Eustis

4.89 out of 5 average rating, 166 reviews

Brivera in the Mountains-20 min to Sugarloaf!

AlexandraRating, 5 stars3 weeks ago

Great place to stay! Everything was perfect for my group and felt very spacious. Great cabin to stay for a group Sugarloaf trip. Pro tip: Like the host describes, in the winter months be sure to drive an all wheel drive car. The driveway is uphill.

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Vacation rentals in Upton

Top-rated vacation rentals in Upton

Vacation rentals for every style

Popular amenities for Upton vacation rentals

Other great vacation rentals in Upton

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