Holiday rentals in Cumberland

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Top-rated holiday rentals in Cumberland

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Top guest favourite
A quaint cottage is illuminated at night, showcasing its rustic wooden exterior and sloped roof. Soft lighting highlights the entrance, leading up a set of wooden steps surrounded by vibrant foliage and stone landscaping, against a backdrop of a deep blue twilight sky.
Cottage in Glenwood City
4.95 out of 5 average rating, 194 reviews

Cozy Farmstead Cottage Getaway

The cottage is located on our 80 acre farmstead in the bucolic rolling hills of Western Wisconsin just over an hour from the Twin Cities. Relax, create, or dream in this peaceful setting. Cherish time with loved ones. Hike along the creek, woodlands and fields. Enjoy the plentiful birds and wildlife. Bring your bike in the summer, and snow shoes in the winter. Cozy up to the wood stove with a hot beverage. Work remotely with our high speed WiFi. We welcome up to two dogs for an additional fee.

Top guest favourite
Place to stay in Saint Croix Falls
4.95 out of 5 average rating, 389 reviews

The Wissahickon Inn - The Cozy Cabin In The Woods

You'll love our cabin in the woods! Once a historic mercantile, the Wissahickon Cabin has been transformed into a cozy cabin for 2 - 4 guests. The cabin is situated in the forest and visible from the Gandy Dancer Trail. The front porch boasts an access path directly to the popular Woolly Bike Trail. Our cabin is secluded in the woods, but it's less than a 5-minute drive to downtown St Croix Falls, Interstate Park, dining, shopping, and entertainment. Enjoy a peaceful getaway in the north woods!

Guest favourite
A modern single-story home is set amidst lush greenery, featuring a welcoming entrance with wooden steps leading to a porch. The exterior is clad in dark gray siding, complemented by large windows that provide natural light, and a manicured garden adding a touch of color.
Cabin in Frederic
4.93 out of 5 average rating, 259 reviews

Up North Retreat: Peaceful & Relaxing But Modern!

Your private getaway up North! Full renovation throughout makes this a tranquil and relaxing, yet modern escape. Enjoy a warm bath in the jacuzzi tub, grab some coffee in the gorgeous custom kitchen with SS appliances, and cozy up to a movie in front of the electric fireplace! Two full bedrooms and baths for amazing privacy. Explore the local scenery by day and Sit around the bonfire by night! You won't find anything this peaceful without sacrificing the modern essentials. Fiber internet, too!

Guest favourite
A cozy tiny home is illuminated at night, revealing warm light from its windows. A stone pathway leads to an inviting front deck surrounded by greenery. Nearby, a decorative lantern can be seen in the foreground, enhancing the serene ambiance.
Tiny home in Saint Croix Falls
4.91 out of 5 average rating, 235 reviews

Wolf Creek Luxury Eco-Tiny Home on the Ridge

Experience our newly-built eco-friendly tiny home perched right on the edge of the ridge above the majestic St Croix River Valley. Enjoy expansive views from the deck, the loft or the many windows looking out over the valley. Enjoy our private electric barrel-sauna, fire-pit, gas grill, pond with canoes and kayak, Wolf Creek with swimming hole or just chill on the ridge watching the many birds and wildlife. Just over an hour drive from the Twin Cities, a romantic and memorable stay awaits you!

Top guest favourite
Cabin in Comstock
4.96 out of 5 average rating, 228 reviews

Nordic Lake Cabin : Sauna/Hot Tub/Pontoon Rental

We finished building this modern Scandinavian cabin in spring 2020. It’s been featured in Vogue and on Magnolia Network. The cabin sits at the end of the road on a private lot with a perfect view of sunsets over the nature side of the lake. Drive past farm fields, into the woods, and onto our private gravel road, arriving at the driveway. Watch loons, tundra swans, eagles, beavers and deer while you relax by the lake. Pontoon boat rental is available as an add on! Pets welcome for a $90 fee!

Top guest favourite
A serene winter scene is presented, with snow-covered trees framing the view of the Apple River in the distance. The landscape is enveloped in a light snowfall, creating a tranquil and picturesque atmosphere. The river is partially visible through the snowy branches.
Cabin in Amery
5 out of 5 average rating, 163 reviews

On River’s Bend Cabin | Wood-stove | Apple River

Perched high on the banks of the Apple River, this timber-framed cabin offers spectacular views of the river and wildlife. We’ve spotted bald eagles, deer, ducks, geese, great blue heron, golden eagle, fox, beaver, bear and wild turkey from the comfort of the cabin. One hour from the Twin Cities, it’s the perfect cabin getaway for couples, friends, and families. Located on private acreage in Amery, WI you will be near rivers, lakes, hiking trails and all that Northern Wisconsin has to offer.

Top guest favourite
A serene entrance is framed by snow-covered trees, with soft light emanating from the cabin's interior. A stone path leads to the door, complemented by a decorative lantern and a stone statue. A blanket of fresh snow creates a tranquil winter ambiance.
Cabin in Grantsburg
4.95 out of 5 average rating, 728 reviews

Quiet Seclusion at Trade River Retreat Cabin

Remote, tranquil, quiet and exceedingly private getaway right on the banks of a protected river, only 1.5 hours from the Twin Cities! Even the beautiful drive there is relaxing. Enter a world of peace and calm deep in the woods. Make delicious meals in a well-stocked modern high-end kitchen, play in the river, relax in the sauna or enjoy a bonfire. This is not your typical cabin but a spiritual eco-oasis with a unique eclectic blend of modern, rustic, Native American and Japanese aesthetic.

Top guest favourite
The exterior of the guesthouse features vibrant orange siding complemented by blue trim and windows. A sturdy wooden staircase leads to the main entrance, flanked by lush green vegetation. The overall architecture showcases a blend of modern and rustic design elements, inviting guests to explore further.
Flat in Hayward
4.93 out of 5 average rating, 247 reviews

THE SUNROOM SUITE @Loon Loon Lake Guesthouse

Only 10 minutes and a world away from Hayward, the stylishly appointed SUNROOM SUITE is part of Loon Lake Guesthouse. Take in the view of gardens, tall pines and glimmering Loon Lake through windows and skylights that overlook this picturesque setting. Summertime brings swimming, canoeing, bird watching and walking the loop. Venture out for some day tripping or work remotely with Starlink WiFi. And be sure to make time for luxuriating in the soaking tub. Life is sweet in The Sunroom.

Top guest favourite
The open living area features large floor-to-ceiling windows, allowing natural light to fill the space. A modern kitchen with stainless steel appliances is complemented by wooden cabinetry. Comfortable seating arrangements include a sleek sofa and a chair, arranged around a glass coffee table.
Cabin in Frederic
5 out of 5 average rating, 283 reviews

Nordlys Lodging Co. - MetalLark Tower

Perched high among the trees with breathtaking views of the hidden lake and wildflower meadows, MetalLark Tower is the perfect getaway. This two-story, 800 sq.ft. cabin has one king bed, one hide-away bunk bed, and one bathroom. We put the living area high up on the second floor to give our guests a bird’s eye view. Floor to ceiling glass brings the outdoors inside, and each season brings its own unique perspective. Staying in MetalLark tower is truly a one-of-a-kind experience.

Top guest favourite
A new house with a modern design is set among lush greenery, featuring a metal roof and large windows. The surrounding area includes neatly arranged evergreen trees and natural stone accents. A gravel driveway leads to the entrance, blending harmoniously with the outdoor landscape.
Tiny home in Grantsburg
4.97 out of 5 average rating, 637 reviews

Snowshoe Creek & Little Wood Lake Tiny House

New 520 sf 'not too tiny' house on 20 wilderness acres. Year 'round fun. Dog friendly. RV & EV plug. Firepit. Your Snowshoe Creek and Little Wood Lake trails. Free canoe, kayak, paddleboat. $40/day mini-pontoon boat. Fishing. Internet. WiFi. AC. Gas Fireplace. Sleep by Number. Lovely bathroom. New gas stove. Ice maker. 2 TVs. 3 towns + Burnett Dairy/Bistro, 4 golf courses, DQ to fine dining, mini-golf, antiquing, multi-theater, Siren beach & 'Music in Park'. Wildlife! You'll return.

Top guest favourite
A spacious deck is presented with multiple seating options, including a high-top table and chairs under large red umbrellas. The view overlooks a serene lake, surrounded by trees, providing a peaceful outdoor space for relaxation.
Cabin in Cumberland
4.89 out of 5 average rating, 195 reviews

Cozy 4-BR Family Cabin on Lake with Scenic Views

Enjoy mornings in a charming lakeside cabin, where breathtaking views greet you from the wrap-around deck just steps from the water. Swim in the clear, sandy-bottom lake, fish from your private dock, or play yard games with family and friends. Relax on the deck, soak in the peaceful surroundings, and as the sun sets, gather around the cozy campfire. With endless opportunities for fun, adventure, and relaxation, this cabin is the perfect setting for creating cherished family memories.

Top guest favourite
Large windows frame serene views of the river and surrounding pine trees, inviting natural light into the space. A cozy area rug lies on the floor, complementing the wood flooring and adjacent to a small kitchenette featuring simple cabinetry.
Cabin in Webster
4.96 out of 5 average rating, 199 reviews

Riverside Retreat- A small cabin for big memories!

Renovated cabin nestled high in the pines overlooking the river. Kick back and relax in this calm, stylish space where the river views will take your breath away. We have a great selection of games, books and movies to snuggle up with in front of our warm fireplace. Bring your snowmobiles, ATVs and ice fishing gear as we are close to the Gandy Dancer Trails and our beautiful river flows to two lakes for great fishing - end at our bonfire pit to roast S'mores and swap stories!

Popular amenities for Cumberland holiday rentals

Quick stats about holiday rentals in Cumberland

  • Nightly prices starting at

    Cumberland holiday rentals start at $192 SGD per night before taxes and fees

  • Verified guest reviews

    Over 190 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Cumberland rentals

  • 4.9 Average rating

    Cumberland stays are highly rated by guests – averaging 4.9 out of 5!

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