Vacation rentals in May

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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 inviting rooftop deck features comfortable seating with decorative cushions, surrounded by potted greenery. Soft lighting from string lights creates a cozy atmosphere, while panoramic views of the St. Croix River and downtown buildings are visible in the background.

Townhouse in Stillwater

Lumberjack Inn DT-on Main St. with a rooftop deck

Welcome to our unique townhome located in a historical building nested into the heart of downtown, offering panoramic views of the St.Croix River.Unwind on the expansive rooftop deck, enjoying a 360 panoramic view of the river, downtown, and the charming historical neighborhood.This gem is also apart of the Union Art Alley, featuring a vibrant mural by a local artist.With dining, shopping, and live entertainment just steps away, your stay promises a perfect blend of culture and entertainment.

4.96 out of 5 average rating, 157 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, 207 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

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.

4.86 out of 5 average rating, 21 reviews

Top 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, 274 reviews

Guest favorite

A comfortable outdoor seating area is shown, featuring a cushioned sectional arranged around a wooden deck. An umbrella provides shade, while a serene view of the lake and boats is visible in the background. Colorful flowers are positioned along the railing.

Guest suite in Forest Lake

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.

4.9 out of 5 average rating, 230 reviews

Top guest favorite

Apartment in Forest Lake

Beauty & Serenity. 6 guests/2 bedrooms!

The space is tastefully decorated! It has two bedrooms with a Day bed with pull-out trundle, a Queen sofa bed in the living room. Has parking & private entry, full kitchen, dining & living room with private full bath, Dish-network TV in each bedroom & living room. Forest Lake is a quaint town 30 minutes from both downtowns of the twin cities. It’s close to the Blaine airport, sports center+Running Aces Casino. It has several shops+ restaurants+ a beach area on Forest Lake!

5.0 out of 5 average rating, 124 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

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 25 minutes 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, 121 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, 215 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, 139 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, 149 reviews