Vacation rentals in Osceola

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Top-rated vacation rentals in Osceola

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Guest favorite

Guest suite in Osceola

4.95 out of 5 average rating, 208 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!

Aug 14 – 21

$90 per night

Guest favorite

Cabin in Grantsburg

4.95 out of 5 average rating, 603 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.

Aug 1 – 8

$166 per night

Guest favorite

Place to stay in Saint Croix Falls

4.94 out of 5 average rating, 169 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. Situated in the forest, the cabin is visible from the Gandy Dancer Trail. The front porch boasts an access path that goes directly to the popular Wolly 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!

Nov 2 – 9

$103 per night

Guest favorite

Cabin in Amery

5.0 out of 5 average rating, 110 reviews

Cabin On River’s Bend

Perched high on the banks of the Apple River, the timber-frame cabin offers spectacular views of the river and wildlife. On the river we see bald eagles, deer, ducks, geese, great blue heron, golden eagle, fox, beaver and wild turkey from the comfort of the cabin. Just one hour from the twin cities, it’s the perfect cabin getaway for couples or families. Located on a private 3-acre lot <10 miles from Amery, WI you’ll be near hiking and biking trails and all that Northwest WI has to offer.

Sep 27 – Oct 4

$209 per night

Superhost

Loft in North Branch

4.79 out of 5 average rating, 150 reviews

Nostalgia Room - 1 Bedroom Loft Apartment w/ Views

Welcome to our modern 1-bedroom loft, centrally located in the heart of downtown North Branch. Housed in a beautifully restored 1920s building with modern decor, you can admire the Americana Coca Cola mural featured on the exterior of the building. The loft's central location means you're just a stone's throw away from essential amenities, including a quaint café, a health food store, and a women's clothing boutique conveniently located below. Everything you need is within arm's reach.

Mar 25 – Apr 1

$81 per night

Guest favorite

Guest suite in Forest Lake

4.95 out of 5 average rating, 154 reviews

Romantic Lakeside Loft.

A wonderful lakeside getaway, with beautiful lake views from your suite and deck. Guest suite includes full kitchen, living room with fireplace, bedroom with attached full bath. Private entrance on side of home with your own private deck for lounging. dining and grilling. Large yard for playing games, fire pit and outdoor tiki bar. Plenty of dock space for boats. Direct access to lake for floating ,paddling, swimming, fishing and relaxing. Paddleboard and kayak available for your use.

Oct 17 – 24

$123 per night

Guest favorite

Tiny home in Grantsburg

4.97 out of 5 average rating, 525 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.

Oct 29 – Nov 5

$125 per night

Guest favorite

Cottage in Balsam Lake

4.97 out of 5 average rating, 100 reviews

Pines That Whisper Cozy Cottage

Escape to the country! Discover "Pines" that Whisper located in rural Balsam Lake WI. Our cozy cottage is only a stones throw away from beautiful Half Moon Lake with public access to the boat launch and swimming beach. Enjoy fishing, kayaking, biking and leisurely walks on country roads. Connect with nature and wide open spaces , we are nestled in a private setting surrounded by farm fields. Envision wildlife passing by, loons calling in the distance, & breathtaking sunsets!

Jan 17 – 24

$136 per night

Guest favorite

Home in Taylors Falls

4.98 out of 5 average rating, 197 reviews

Maple House - Spacious 6 BR home for gatherings

ALL are welcome in private home above quaint village of Taylors Falls. Perfect for family stay-cations, vacations, groups & friends gatherings to relax or work. High speed wifi, cooking facilities, natural setting, fire pit, and private parking for 9 regular size cars. We follow Covid 19 enhanced cleaning guidelines with UV lights and HEPA filters on furnaces/air conditioners. Please reflect total number of guests in reservation.

Apr 22 – 29

$396 per night

Guest favorite

Apartment in Amery

4.94 out of 5 average rating, 176 reviews

Serendipity Escape - Relax and enjoy nature!

Winter is here! So if you enjoy skiing, snowboarding, cross country skiing, or ice fishing. Just minutes away from Trollhaugen and Wild Mountain Ski resorts. Serendipity Escape on Lake Wapogasset! Available 365 for up to 4 guests, age 12 and older. Full Self Check-In. Fully equipped efficiency apartment with private entrance. Check out all our amenities provided for your convenience and perfect for a relaxing getaway.

May 28 – Jun 4

$84 per night

Guest favorite

Farm stay in Dresser

4.94 out of 5 average rating, 271 reviews

Quaint and Quiet Farm Retreat by Trollhaugen

Come enjoy country living just an hour northeast of the Twin Cities. Modernized guest house on 16 acres surrounded by rolling farmland, prairie, and trees. Very peaceful and secluded with the sounds of nature all around. Visit Trollhaugen down the road for skiing or snowboard in the winter and zip lining in the summer. Located 10 minutes from Osceola, St. Croix Falls and Taylors Falls. Polk County ID #: 76776

Jul 8 – 15

$119 per night

Guest favorite

Loft in Saint Croix Falls

4.97 out of 5 average rating, 136 reviews

The Artists Loft - Romantic Historic OMG

The Artist's Loft is a private open concept 1 bedroom apartment with queen size bed and full-size comfortable deep couch in the living room and a twin size daybed to sleep up to 4 adult guests. A single air mattress can be added for children. Beautiful, unique, spacious, full kitchen and is located at the gateway to the outdoor adventures of the St Croix Valley! Follow us on insta @123swashington

Aug 21 – 28

$184 per night