Holiday rentals in Upton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Upton

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

1 of 1 pages1 / 1
Superhost
The log cabin, set against a clear blue sky, features a peaked roof and large windows that reflect the natural surroundings. A front porch with a railing extends from the cabin, surrounded by patches of snow and green trees, enhancing its secluded ambiance.
Cabin in Andover
5.0 out of 5 average rating, 201 reviews

Mountain Time Cabin,Spectacular Views! Secluded!

Looking for a mountain cabin getaway? You have found it here at Mountain Time Cabin! This cabin is new and absolutely beautiful! Located in the Western Mountains of Maine - a true paradise for the outdoor enthusiast. Bring your Snowshoes,Skies,Snowmobiles, or hike right from the front door with a 130 acres of trails to explore. Enjoy the spectacular views of the mountains and the cascading brook all from sitting in the recliners with the warmth of the pellet stove Has AC and pool table.SECLUDED!

Top guest favourite
Cabin in Andover
4.98 out of 5 average rating, 159 reviews

Bearbrook: River, hikes, nature, adventure, relax

Take it easy at this unique and tranquil getaway. Bearbrook Cabin, nestled on the side of a mountain, offers modern amenities in a rustic natural setting. Watch the brook run down the mountain while sipping coffee on the deck. Listen to the birds and river while working remotely in the sun room. Conveniently located to 4-season recreation: hiking, hunting, fishing, swimming, boating, skiing, snowmobiling, ATVing and more. 30 min from Rumford, Bethel, Sunday River, Black Mountain, and Mt. Abram!

Top guest favourite
The exterior of the white chalet features a modern design, with large windows framing the entrance. Two Adirondack chairs are positioned on a gravel driveway, surrounded by natural stone landscaping and trees that provide a serene backdrop.
Home in Rangeley
4.97 out of 5 average rating, 77 reviews

White Chalet on the Hill

Welcome to the White Chalet in Rangeley! Have fun with the whole family at this stylish place! With Great views of Saddleback, a great location directly between Oquossoc and Rangeley Villages, and all the amenities of a modern well-equipped home, you'll love your stay here! The Home boasts 3 bedrooms, a private office/sleeping room, two full bathrooms, fully equipped kitchen, memory foam mattresses throughout, Smart TV's in all bedrooms, hi speed wifi & plenty of parking for trucks & trailers

Guest favourite
A charming cabin sits prominently in a lush green landscape, surrounded by dense trees. The structure features a sloped roof and a welcoming front porch, while the natural, wooded surroundings create a serene and private retreat.
Home in Errol
5.0 out of 5 average rating, 12 reviews

Errol Hill Escape

Forget your worries in this spacious and serene space. The perfect getaway for outdoor enthusiasts and anyone looking for a peaceful getaway in the beautiful North Country. 2.5 miles to ATV trails and downtown Errol home of the famous LL Cote. 2 miles to the Androscoggin River and Northern Waters Outfitters. 5 miles to stunning Lake Umbaggog state park. Explore our 11 acres of woods and be on the lookout for an abundance of wildlife. Relax on the expansive decks and enjoy Mountain View’s.

Top guest favourite
A bright living area features large windows that provide expansive views of the lake and mountains. Comfortable seating includes a spacious sofa with decorative pillows and two armchairs. A wooden coffee table stands at the center, while natural light enhances the calm atmosphere of the space.
Home in Roxbury
5.0 out of 5 average rating, 12 reviews

Luxury Roxbury Pond Lakefront

Book your summer escape today! Swimming, paddling, and sunny days on the water await. We also have plenty of space for your guests. Northwind Lodge offers four seasons of luxury comfort on the banks of Roxbury Pond. Enjoy sweeping lake and mountain views from every angle in stylish, relaxed surroundings. Cook in the full kitchen with brand‑new appliances while staying connected with family and friends in the open‑concept layout. Four bedrooms ensure everyone has room to unwind in comfort.

Top guest favourite
Cabin in Upton
4.97 out of 5 average rating, 73 reviews

Elk Lodge- Upton

Recently updated and added a second bathroom and 4-6 person barrel sauna. Located minutes from Grafton Notch State Park and immediate access to snowmobile trails. Umbagog Lake boat launch located 3.7 miles away. Across property of Umbagog National Wildlife refuge. Only 37 minutes to Sunday River Ski Resort. Elk Lodge is a log cabin with the perfect surroundings of nature. Enjoy your morning coffee on the porch, catching glimpses of the wildlife. Excellent area for outdoor recreation.

Top guest favourite
The spacious deck offers a clear view of the lake, featuring a private dock with boats. Lush greenery borders the waterfront, and distant mountains are visible under a bright sky, providing a serene outdoor setting.
Home in Errol
5.0 out of 5 average rating, 41 reviews

L' Akers Cottage

Enjoy this Cozy Lake house with a private dock and swimming area. Relax on the large over sized deck while observing the wildlife on the lake. Right next to the property is a public boat launch where you can launch your boat and have it tied to the cottages private dock for easy access. Also available with property is a peddle boat and kyak for your use. ATV trail access is 1/2 mile up the road. In the wintertime, you can snowmobile right from the property to the main trail system.

Top guest favourite
Home in Rangeley Plantation
4.96 out of 5 average rating, 24 reviews

Valhalla | Waterfront Retreat on Mooselookmeguntic

Welcome to Valhalla — your private lakefront retreat on the south shore of beautiful Mooselookmeguntic Lake. Set on 4 secluded waterfront acres, Valhalla is the perfect place to unplug, reconnect, and experience classic Maine lake life. Spend your days boating, swimming, kayaking, fishing, and gathering around the firepit under the stars. Whether you’re planning a summer lake week or a snowy winter escape, Valhalla offers an unforgettable Western Maine getaway for families and groups.

Top guest favourite
A spacious open-concept living area is highlighted by warm wood paneling and vaulted ceilings. Large windows allow natural light to fill the space. A rustic dining table made of reclaimed wood is positioned alongside a cozy seating area featuring multiple sofas and decorative lighting.
Cabin in Andover
4.99 out of 5 average rating, 101 reviews

Modern Mountain Chalet! Hike, Swim & Treasure Hunt

Welcome to Stony Brook Chalet, a modern chalet nestled in the foothills of the White Mountains in beautifully rugged Western Maine. Disconnect from the hustle and bustle of daily life and enjoy a serene, private getaway. Located on almost 3 acres of land surrounded by trees, complete with a private hiking trail, Stony Brook Chalet offers seclusion with close proximity to several stunning hikes, lakes, and ski resorts. *Up to 2 dogs are welcome in accordance with house rules*

Top guest favourite
Home in Newry
5.0 out of 5 average rating, 57 reviews

Cozy Modern Mountain Cabin~

A unique mountain getaway for skiers, hikers, outdoor enthusiasts, and those who just want to relax next to a river in the woods 🌲 🏔 10 minutes from the ski slopes at Sunday River, steps from hiking trails all throughout the Mahoosuc Mountains, great for snow shoer’s, snowmobiles, ATV’s, & jumping into a swimming hole ~ It’s the perfect place for a couple, few friends, or family to enjoy the Western Mountains of Maine while having your own unique cabin to call home ~

Top guest favourite
Treehouse in Woodstock
4.98 out of 5 average rating, 322 reviews

LuxuryTreehouse w/ Hot Tub Near Sunday River

Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.

Top guest favourite
A log cabin with a welcoming design features four prominent gabled windows on the upper level. The earthy tones of the wood blend harmoniously with the surrounding greenery. A wooden walkway leads from the lakeside, enhancing accessibility to the cabin's entrance.
Cabin in Weld
4.95 out of 5 average rating, 141 reviews

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.

Popular amenities for Upton holiday rentals