Vacation rentals in Cumberland

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Top-rated vacation rentals in Cumberland

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Top guest favorite
A light-filled living space features a comfortable leather sofa, a wooden coffee table, and a flat-screen TV mounted on a wooden cabinet. A round dining table with two chairs is positioned near the window. Decorative horse-themed accents are visible on some furnishings.
Guest suite in Osceola
4.96 out of 5 average rating, 279 reviews

Cozy Mother-In-Law Apartment—No Cleaning Fee!

Voted 2021 and 2023 Readers’ Choice Best Bed & Breakfast! Steal your getaway at one of Osceola’s most historic estates. Wonderfully nestled in the St. Croix Valley, this apartment’s location will not disappoint. You’ll be a brief walk from beautiful downtown Osceola, close enough to explore the great outdoors, and a short distance from all that the Twin Cities has to offer. You’ll get a cozy and comfortable layout, thoughtful amenities, attached heated garage, and assistance just a message away!

Top guest favorite
Place to stay in Saint Croix Falls
4.95 out of 5 average rating, 429 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!

Top guest favorite
A charming cabin features a gabled roof and a welcoming wraparound deck. Surrounded by vibrant autumn foliage, a picnic table sits on the leaf-strewn ground, providing an inviting outdoor space. The structure is nestled among trees, enhancing the feeling of seclusion.
Cabin in Comstock
4.91 out of 5 average rating, 266 reviews

Secluded Lake Cabin + Hot Tub

A private secluded lake cabin retreat north of Turtle Lake, WI. Downstairs consists of a living room w/sofa sleeper, kitchen, and bathroom. The upstairs has 1 bedroom with a queen, a bed in the open loft and 1/2 bath. Drive by grazing cows and farm fields into the woods, onto a private gravel road, and down a long winding wooded driveway to our lake retreat! We don’t recommend visiting in winter without 4 wheel drive! Pontoon boat rental is available as an add on! Pets welcome for a $90 fee.

Top guest favorite
Cabin in Birchwood
4.98 out of 5 average rating, 106 reviews

The Bunk House Lakefront Cabin in Birchwood, Wi

Newly remodeled Lakeside Cabin on beautiful, spring fed, Spider Lake chain. The cabin is 4 season with 3 bedrooms and 2 bathrooms. Enjoy brand new stainless steel Fridgaire Gallery appliances with a view of the lake from every window! Feel free to use the 2 person Canoe and three childrens Kayaks to explore the crystal clear chain of 6 Lakes. 75% of the lake is Ntl. Forest making it one of the most peaceful and quite lakes around. Great Crappie, Blue Gill, Bass and Northern fishing. ENJOY!

Top guest favorite
A red cabin with a sloped roof is nestled among tall trees, surrounded by a lush green landscape. Large windows are framed in white, allowing for natural light. A concrete patio leads to the entrance, offering easy access to the serene outdoor setting.
Cabin in Comstock
4.95 out of 5 average rating, 44 reviews

Cozy Lake House in the Woods!

Relax at this cozy 1-bedroom, 2-loft lake house on nearly 3 acres of woods! The property is situated on the shore of Lake of the Woods, a private lake great for swimming, kayaking or slow cruising with pontoons or small boats. Enjoy high-speed water sports at nearby Pipe Lake and Beaver Dam Lake. You’ll be a short 15 minute drive from St. Croix Casino in Turtle Lake, and golf, shopping, eateries and coffee shops in Cumberland. You will appreciate the lakeview at this cabin year round!

Top guest favorite
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, 675 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 favorite
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.

Superhost
The living room features a combination of handcrafted log walls and a large stone fireplace. Two cozy chairs and a lamp invite relaxation, while a wooden table sits nearby. Natural light filters through the glass door, leading to an external porch, with shelves holding various games.
Cabin in Sarona
4.91 out of 5 average rating, 289 reviews

Hunt Hill's Rustic Log Cabin

Welcome to Hunt Hill Nature Center! We are a public, non-profit learning center and nature sanctuary. Our historic Log Cabin is nearly a century old and offers a peaceful retreat in the woods. All the furniture was updated in 2018. The Log Cabin is located just outside of the main camp, settled on top of a hill overlooking pristine forest habitat. Nearby towns offer additional entertainment or relax in our quiet setting while reading a good book in front of the stone fireplace.

Guest favorite
The entrance features a wooden door framed by stone pillars, with potted flowers at the base. A covered porch provides shade, while natural light filters through the windows and the surrounding trees create a serene atmosphere.
Barn in Cumberland
4.88 out of 5 average rating, 26 reviews

Four Seasons of Cabin Fun - Bunkhouse Retreat

This relaxing and open concept renovated barn is perfect for your nature retreat. Located on a secluded bay of the lake, this place provides a relaxing getaway in any season. Use the paddleboards, kayaks, and canoes in the summer and enjoy snowmobiling on the nearby trails or snowshoe around the property in the winter. Just a 1.5 hour drive from the Twin Cities! You will be greeted by a stone gate and quarter-mile driveway lined by maple trees on your way into the property.

Top guest favorite
An open concept area features a vaulted ceiling with a large archway adorned with string lights. A cozy kitchenette is visible, along with rustic wooden walls and charming decor creating a warm space. An inviting atmosphere is enhanced by the soft illumination throughout.
Cottage in Rice Lake
4.99 out of 5 average rating, 139 reviews

Stonehaven Cottages The Turtle cottage

Slow and steady wins the race! We are tickled to introduce our second cottage "The Turtle" here at Stonehaven Cottages on Tuscobia Lake, LLC. We put in a large archway in the vaulted ceiling to give it a look and feel of being inside a turtle shell. This cozy cottage has an open concept with full kitchen, one small bedroom and a queen sofa sleeper. It also has a spectacular view of Tuscobia Lake! When life gets too busy, come and slow down a bit at "The Turtle"!

Guest favorite
Chalet in Turtle Lake
4.9 out of 5 average rating, 102 reviews

Turtle Lodge on Upper Turtle Lake

Beautiful Log Cabin 90 minutes from the Twin Cities and steps away from prime recreational/fishing lake. Enjoy the deck overlooking lake and fire pit. In the evenings, enjoy dinner on the deck, tell stories around a campfire, savor s'mores and listen to the loons. The dock is out of the lake from Oct 1st until the week before memorial weekend. Only minutes from the ATV and Snowmobile Trails. Pontoon rental not available.

Top guest favorite
A modern tiny cabin is nestled among tall trees, showcasing large windows that blend with the natural surroundings. A spacious deck features comfortable seating, inviting guests to relax in the serene landscape. The earthy tones of the cabin harmonize with the lush greenery of the forest.
Home in New Auburn
4.97 out of 5 average rating, 37 reviews

Open Air Outpost - Aldo Tiny Cabin

The Open Air Outpost is a restorative nature retreat, two hours from the Twin Cities. Enjoy your stay in the luxurious Aldo tiny cabin on 18 secluded acres on a private, non-motorized lake. Thoughtfully designed by the creators of the Open Air Humans podcast, the Outpost is the place to unplug and restore yourself in a place of quiet beauty.

Popular amenities for Cumberland vacation rentals

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  4. Barron County
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