Vacation rentals in May

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in May

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

An old railway bridge spans a calm river, surrounded by lush green trees along the bank. The bridge features a rusted metal structure, with wooden railroad ties visible along the track extending toward the horizon under a clear blue sky.

Cabin in Scandia

River Haus Where Good Times&Great Memories Happen!

The River Haus is located on 59 wooded acres with 1200 ft. of riverfront. The home is tucked back in the woods with a 3/4 mile long private drive, offering complete privacy. There are beautiful views of the St. Croix River from the deck, access to the river, dock, and amazing walking trails. The home is a log- sided cabin from the 1930s maintaining its original charm with vaulted ceilings, wood beams, and wood floors. Near downhill & cross-country skiing at Wild Mt. & William O'Brian State Park

4.99 out of 5 average rating, 104 reviews

Top guest favorite

A charming two-story home with a yellow exterior is presented, showcasing a welcoming front porch adorned with hanging planters. The roof features gables and multiple windows, contributing to its classic design. A spacious lawn leads to a paved walkway, offering easy access to the entrance.

Townhouse in Osceola

Dr Combacker’s Historic 1880s Home

Voted 2021 & 2023 Readers’ Choice Best Bed and Breakfast! Historic charm marries modern luxuries in this beautiful 1880s home. Built by the pioneering Dr. Henry Combacker, this one of a kind home boasts original woodwork and amazing craftsmanship. Families and groups alike will enjoy the fully stocked kitchen, outdoor living spaces, entertainment for all ages, attention to detail, and close to downtown location. Dr. Combacker’s has all you need for a calm, relaxing stay in and out and about.

4.98 out of 5 average rating, 206 reviews

Top guest favorite

A charming cabin is set against a lush green lawn, with large windows reflecting the warm hues of sunset. Tall trees provide shade to the exterior, while a screen porch offers an inviting space for evening relaxation. The serene lakefront is visible in the background.

Cabin in Marine on St. Croix

Superb Shore Side Cabin-AMAZING location and view!

This is a 1-of-a-kind, rare find! Imagine a remote northern lake, loons, frogs, eagles, panoramic views of the stars & realize you’re only 30 minutes from town! No hassle of driving 4 hrs north to be stuck on a lake with a 1000 other people & neighbors 2 feet f/you -this is remote w/o being remote! Look no further, you’ve found it!Convenient, safe, wifi, memorable moments just waiting for you! This little gem won’t disappoint! NOTE: NO NEED TO CONTACT ME TO ASK IF IT’S FOR SALE -IT ISN’T. 😃

5.0 out of 5 average rating, 30 reviews

Top guest favorite

The living room features large windows allowing soft natural light to brighten the space. A cozy seating arrangement includes two black armchairs and a spacious gray sofa. A central round coffee table is complemented by a decorative piece, and a small side table is positioned beside the sofa.

Home in Hudson

DT Hudson Home w/Hot Tub, 1 block from Riverwalk!

Step into history at our 5-bedroom downtown Hudson retreat! Nestled just 4 blocks from shopping and dining, and only 1 block from the historic St. Croix River, this home seamlessly combines modern comfort with timeless charm. Gather your friends or family and enjoy dining, shopping, nature, and the many other local attractions in Hudson...then, come back and refuel in this comfortable space with a hot tub! Immerse yourself in downtown Hudson and relax and enjoy a beautiful, historic home.

5.0 out of 5 average rating, 135 reviews

Guest favorite

Apartment in Stillwater

Lakefront Villa at Golden Acres

Welcome to our fully remodeled, lakeside apartment nestled above the main office at Golden Acres Campground on beautiful Square Lake. This one-bedroom, one-bath retreat offers panoramic views of the lake and campground, thanks to large windows throughout and a brand-new private deck that overlooks it all. While the apartment has been fully modernized—complete with a new bathroom, granite countertops, and a private deck—it still holds a vintage charm and all the perks of campground living.

4.85 out of 5 average rating, 20 reviews

Guest favorite

A light and airy living room features two comfortable sofas, a round coffee table, and a woven rug. Large windows allow natural light to filter in, complementing the neutral color palette. A potted plant adds a touch of greenery to the inviting space.

Cottage in Arden Hills

Heirloom Cottage | Wooded Retreat, Hot Tub & Sauna

A beautiful 1920s cottage on 1.2 wooded acres on a quiet Arden Hills street, 15 minutes from Minneapolis and St. Paul. It feels a world away. Cared for by Luke and Beka. Cozy fireside sitting room, peaceful sunroom with a hanging swing, well-stocked kitchen with a coffee bar, and a glass-walled backyard studio. Hot tub and sauna open year-round. Comfortable beds and thoughtful touches. Sleeps 10. Built for friend trips, family weekends, and anyone who could use a good exhale. Come rest.

4.96 out of 5 average rating, 269 reviews

Top guest favorite

An outdoor patio space features a dining table surrounded by chairs, with an umbrella for shade. A hot tub is positioned nearby, and a section of the deck is adorned with a patterned rug. Lush greenery provides a natural backdrop.

Home in Stillwater

Private Stillwater Oasis/Hot Tub/5 min to DT

📍3 wooded acres • 5 minutes to downtown Stillwater & the St. Croix River • 5 bedrooms | 4 bathrooms • Fully stocked kitchen • Multiple gathering spaces • Hot tub • Fire pit • Outdoor dining • Private backyard oasis Perfect for: • Girls’ getaways • Bachelorette getaways • Family vacations • Friends’ weekends Enjoy a peaceful setting just minutes from restaurants, shopping, wineries, breweries, and the riverfront. 📆 Book your Stillwater getaway today! License #2026-01

5.0 out of 5 average rating, 23 reviews

Top guest favorite

A single-story home is framed by lush greenery and flowering shrubs. The entrance features a decorative door and stone accents, while a well-maintained lawn leads to the front. The surrounding trees provide a natural setting, enhancing the peaceful environment.

Guest suite in Stillwater

Loons Nest in Stillwater, MN

Entire lower level of home is yours with a private entrance. Welcome to Loons Nest! Located minutes from Stillwater… the 1848 Birthplace of Minnesota located on the scenic St. Croix River! A place where authentic paddle wheel riverboats and gondolas glide the waters. Historic Main Street shopping, dining, lodging and entertainment are yours inside this charming town. Beautiful Stillwater is a short drive from the Twin Cities of Minneapolis/St. Paul and Wisconsin border.

4.99 out of 5 average rating, 210 reviews

Top guest favorite

The exterior of the home features a combination of stone and wood elements, set against a backdrop of vibrant autumn foliage. A chimney is visible on the roof. The surrounding trees contribute to a serene atmosphere, while a fence delineates the property.

Home in Mahtomedi

Stone home, walk to lake + paddleboards

Enjoy chic cabin vibes, just 25min from the twin cities in the suburban small town of Mahtomedi. Our home is the private top level of a duplex in a tree-filled, quiet and family-friendly neighborhood. Take a quick walk to the crystal clear, White Bear Lake or stroll the endless wooded paths, access just steps away. - Stillwater - 15min - St Paul- 20 min - Downtown White Bear - 5min - MSP Airport - 30 min Perfect for: - Girls weekend - Wedding guests - Family visits

4.97 out of 5 average rating, 119 reviews

Guest favorite

The modern retreat features an expansive outdoor patio with comfortable seating arrangements. Large windows accentuate the two-story structure, revealing a seamless blend of indoor and outdoor living areas. Surrounding tall trees provide a sense of isolation and tranquility.

Home in Somerset

Artful Countryside Retreat • Hot Tub • Fire Pit

Secluded, modern, stylish retreat nestled in mature pines on 2.5 acres near Apple Lake. Enjoy a large hot tub, fire pit and year-round activities. The property sits on a lagoon that is currently separated from the lake due to low water levels. The lagoon is suitable for kayaking, pedal boating and fishing, but not swimming. Large windows and sliding doors connect indoors and out, with a patio and rooftop deck. For more design and seasonal moments, find us @StaysInColor.

4.96 out of 5 average rating, 138 reviews

Top guest favorite

An aerial view captures a spacious rural landscape featuring two silos and a large barn amidst colorful autumn foliage. A serene river lies in the background, with a bridge connecting the distant shore. The area is surrounded by cornfields, highlighting the agricultural heritage of the property.

Farm stay in Hudson

Betty's country farmhouse near Stillwater, MN

Spend some time in the country with this 1930's farmhouse that has tons of character, updates and unique style all its own. This was originally a working dairy farm and we are the 4th generation owners. Step into some history and charm with this updated nostalgic home. Main level full bathroom has been completely redone. Sit on the back porch and relax or take a 5 minute drive to historic Stillwater or Hudson and everything the St. Croix Valley has to offer!

5.0 out of 5 average rating, 147 reviews

Top guest favorite

A two-story home is illuminated under a clear sky, surrounded by bare trees. A spacious deck with railings wraps around the upper level, while multiple steps lead down to a lower wooden path. Outdoor seating and tables are visible on the deck.

Home in Marine on St. Croix

Big Marine Lakeside Retreat

Welcome to Big Marine Lakeside Retreat. This beautiful lake home, right on the east bay of Big Marine Lake is just waiting to host you and your memories. The home features a newly remodeled kitchen with all new appliances and plenty of counter space. The open concept main level opens up to a cozy living space with vaulted ceiling and a wall of windows to enjoy the beautiful view of the lake. Big Marine Lake is known for its clear water and great fishing!

4.91 out of 5 average rating, 70 reviews