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
5 out of 5 average rating, 190 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, 139 reviews

Bearbrook: Cozy mountain escape

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
A charming chalet is surrounded by a winter landscape, featuring a wooden exterior and large glass windows. The deck offers outdoor seating options, and a fire pit is visible in the snowy yard. Leafless trees create a serene, rustic atmosphere.
Cabin in Stoneham
4.99 out of 5 average rating, 205 reviews

Mad Moose Lodge• Secluded Cabin w/ Mountain View’s

Welcome to the Mad Moose Lodge! Year-round adventures begin at this 2-bed, 2.5-bath Stoneham chalet. This vacation rental provides incredible fall foliage views and easy access to mountains and lakes! Close by to cross-country skiing and snowshoeing in the winter and hiking, mountain biking, boating and swimming in the summer there are endless options of outdoor enjoyment. Enjoy stunning sunsets over the mountains from the comfort of the couch, or while enjoying a game of pool in the game room!

Guest favourite
A private hot tub is surrounded by trees displaying vibrant autumn leaves, with a gentle stream flowing nearby. A fire pit sits beside the hot tub, offering a cozy gathering space. The cabin's exterior features wooden siding and large windows that invite natural light.
Tiny home in Norway
4.94 out of 5 average rating, 238 reviews

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

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
4.99 out of 5 average rating, 507 reviews

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.

Guest favourite
A spacious outdoor setting features a fire pit surrounded by multiple wooden Adirondack chairs in varying colors. The cozy cottage is visible in the background, nestled among trees and greenery. A picnic table and a shed are also present, contributing to the inviting atmosphere.
Cottage in Bethel
4.88 out of 5 average rating, 100 reviews

Cozy Cottage w/ Lil' Pond, Fenced Yard & Firepit

A quick 2 min. drive to the awesome village of Bethel, recently voted best ski town in North America. The house is only 12 minutes to Sunday River. You and your family will feel right at home in this cozy, private cottage with it's own pond. Also, a short drive to Woodstock, Mt. Abram, and more Western Maine adventures! Come stay, relax in the fenced in yard and enjoy the stars around the fire pit. Fast wifi, RokuTV, BBQ grill , foosball and more! Dogs allowed but please let us know :)

Top guest favourite
A spacious outdoor patio features four green Adirondack chairs arranged around a stone fire pit. In the background, rolling hills are visible under a blue sky with scattered clouds, providing a serene setting for relaxation.
Cabin in Bethel
4.92 out of 5 average rating, 153 reviews

Epic Views, Hot Tub, Game Room, Fire Pit, Dogs Ok

✔ Modern 4-Bedroom, 4-Bath Cabin – Sleeps 12 ✔ Relax in a 7-Person Hot Tub Under Cozy String Lights ✔ Game Room with Bar, Air Hockey, Shuffleboard, & SMART TV ✔ 15 Min to Sunday River & Mt Abram, 10 Min to Downtown ✔ Patio with Fire Pit, Adirondack Chairs, Dining Areas, and BBQ Grill ✔ Spacious Deck with Stunning Views of Sunday River & Mahoosuc Mountains ✔ Cozy Gas Fireplace, A/C, and Fast Fiber WiFi ✔ Dog-Friendly (w/ fee) ✔ High Chair, Pack N' Play, & All Linens/Towels Provided

Top guest favourite
An aerial view of a charming red cabin nestled beside a calm lake, surrounded by lush greenery and tall trees. The property features a small dock extending into the water, with a grassy area leading to the cabin, enhancing the natural setting.
Cabin in Pittsburg
4.95 out of 5 average rating, 202 reviews

Back Lake Waterfront - ATV/Snowmobile Trail Access

The location of this charming and private cabin is perfect for your Pittsburg getaway. Located on a short dead end road you will immediately absorb the peaceful atmosphere and beautiful lake front scenery with just under 100' of frontage. This cabin has both ATV and snowmobile access without the need to trailer from the property. The boat launch is conveniently located 1/8 of a mile away and the local beach is a short paddle across the lake using the provided canoe and kayaks.

Top guest favourite
Home in Whitefield
4.97 out of 5 average rating, 267 reviews

Sunny Waterfront Cottage at FarAway Pond

Spring Skiing! Sugar and Snow 20%discount! March is maple sugar and BIG snow season at Bretton Woods (only 20 min. away). This bright, wood lined cottage has all you need for a peaceful getaway-Hot Tub in private pavilion, Japanese soaking tub, (small) Heat/AC, +fast wifi. Cook in the kitchen or grill in the beach side pavilion. With 68 acres + miles of trails to a nearby state forest, this is the perfect base for peak-season skiing and serene winter adventure. Dogs welcomed!

Top guest favourite
The exterior of the home is showcased, featuring a green metal roof and dark wood siding. A decorative weather vane sits atop the roof, while window boxes filled with colorful flowers enhance the front façade. A welcoming porch with white railing is visible beside the entrance.
Guest suite in Gorham
4.97 out of 5 average rating, 491 reviews

Cozy comfort close to White Mountain attractions!

A warm and welcoming home away from home! Located in a quiet residential neighborhood in Gorham NH, in the heart of the White Mountains with all of its attractions. Hiking, ATVing, sight seeing, skiing, fishing, kayaking, all right here! This cozy suite is within walking distance to the town center which has a beautiful park and good eating and drinking. There is plenty of parking and ATV's are welcome. Sleeps 4 with a full sized bed and sleeper sofa!

Top guest favourite
An aerial view showcases Maryam's Mountain Chalet surrounded by a snow-covered landscape, with trees and rustic cabins nearby. The distant mountains provide a scenic backdrop, and the iconic Sunday River ski resort slopes are visible, enhancing the chalet's ideal location for winter activities.
Chalet in Newry
4.94 out of 5 average rating, 112 reviews

3 min to Sunday River w/ Views, Game room, Hot tub

Welcome to Sunday River Escape! Nestled in the heart of Newry, Maine, Maryam's Mountain Chalet is a 5.0★ retreat designed for families, friends, and groups seeking both adventure and relaxation. With 5 beautifully appointed bedrooms, 9 comfortable beds, and 4 baths, it's the perfect retreat for families and large groups. 📍 Prime Location ✦3 min to Sunday River Ski Resort ✦15 min to Bethel Village ✦Minutes from hiking at Grafton Notch State Park

Guest favourite
A spacious living area features large triangular windows that frame views of the surrounding mountains. Wooden walls and ceilings enhance the natural setting. Comfortable seating is arranged, alongside a dining table, and a full kitchen is visible in the background, inviting relaxation and gatherings.
Chalet in Newry
4.83 out of 5 average rating, 105 reviews

SUNDAY RIVER VIEWS!! Minutes from the mountain!

Privately situated 4.5 acres on a private hillside in the Sunday River Valley with PANORAMIC VIEWS of all the trails in Sunday River Ski Resort. This 4+bedroom/3 bathroom chalet sleeps 14. The bright and sunny main level has an open floor plan with a beautiful stone fireplace in the living area. The daylight basement has a second living area with a hearth and a wood stove. Enjoy the oversized wrap around deck complete with grill and 7-seat hot tub!

Popular amenities for Upton holiday rentals

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