Holiday rentals in Upton

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Top-rated holiday rentals in Upton

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Top guest favourite

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

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!

FamilyValueAmenities

5.0 out of 5 average rating, 202 reviews

Top guest favourite

Cabin in Andover

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!

LocationValueLayout

4.98 out of 5 average rating, 159 reviews

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

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

FamilyLocationGetting around

4.97 out of 5 average rating, 77 reviews

Top guest favourite

A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.

Cabin in Hanover

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

ValueFamilyRiver

4.99 out of 5 average rating, 548 reviews

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

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.

LocationHeatingAmenities

5.0 out of 5 average rating, 12 reviews

Guest favourite

The spacious orange house features a simple façade with a central entryway flanked by windows. A large front yard is visible, bordered by low shrubs and trees in the background against a partly cloudy sky.

Home in Errol

A Big House in the Heart of Errol

Take a step back in time to grandmas vintage house. This spacious home is located next to the Androscoggin River, perfect for white water rafting trips, hunting, fishing, hiking and boating. The state boat launch is a half-mile down the road. The house has a game room with an air hockey table and board games. There is plenty of room for a large group of people, a two-car garage, and a big front and back yard. Snowmobile trail and ATV access directly from the house. Enjoy high speed WiFi.

ValueFamilyAccuracy

4.95 out of 5 average rating, 40 reviews

Top guest favourite

Cabin in Upton

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.

FamilyValueTV

4.97 out of 5 average rating, 73 reviews

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

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.

FamilyValueAmenities

5.0 out of 5 average rating, 42 reviews

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

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*

FamilyValueQuiet

4.99 out of 5 average rating, 102 reviews

Top guest favourite

An open-concept living area features a spacious sectional sofa, a coffee table, and a large smart TV mounted on the wall. High ceilings with wooden beams enhance the room, while large windows allow natural light to fill the space, creating a welcoming atmosphere.

Home in Rumford

River Valley Sunset Retreat Bethel & Newry Skiing

Your adventure begins at River Valley Sunset Retreat. Nestled on 8.75 private acres in Rumford with stunning mountain and sunset views, this spacious rental is your gateway to Western Maine's best. A skier's dream, it's approximately 20 minutes from Sunday River, Black Mountain, and other premier resorts. Step directly onto the property to cast a line into the adjacent Androscoggin River. Discover the ultimate four-season escape tailored for families and outdoor enthusiasts.

FamilyLocationBathroom

4.98 out of 5 average rating, 113 reviews

Top guest favourite

Home in Newry

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 ~

FamilyLocationCheckout

5.0 out of 5 average rating, 59 reviews

Top guest favourite

Treehouse in Woodstock

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.

ValueFamilyKitchen

4.98 out of 5 average rating, 324 reviews