
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.

South Hill Carriage House-Walk Downtown
Spacious, remodeled guesthouse. 1/2 mile walk to downtown. Live like a local when you stay on Stillwater’s historic South Hill. Located in a prime location, it’s easy to walk to downtown & the riverfront. Stroll a few blocks to “uptown” where the locals go for a burger-n-beer, fresh baked goods, & brunch. Go out and enjoy the St. Croix Valley in all it has to offer, incl. the St. Croix River, great restaurants, shopping, sightseeing, and so many outdoor activities. Or stay home and...just relax.

Harriet Carriage House Adorable 1BR with fireplace
Enjoy a quiet stay in this stylish, centrally located Stillwater Carriage House apartment. This private, stand-alone apartment is just under a mile walk to downtown Stillwater, a few blocks from hand-roasted coffee, a historic neighborhood bar, amazing boozy pies, the Summer Farmer's Market, and Nelson's Icecream Shop. Our gem is poised to please with the atmosphere of a boutique hotel, the convenience & privacy of an apartment, and a gateway to nature, culture, and lasting memories. Lic# 2022-6

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!

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!

Bright & Comfy Stillwater Loft Apartment
Welcome! We're so glad you've chosen to stay at our sunshiny, spacious Stillwater apartment! You will have everything you need for your St. Croix River Valley adventure! Whether you're snuggling in on a wintry weekend, using this as home-base for summer explorations, or unwinding after a historic downtown event, you'll find all your creature comforts met while planning your next outing. Simply a mile from the historic downtown and river areas, you'll have easy access to the best of Stillwater!

Location, Comfort, Amenities! Downtown Hudson, WI!
*As seen in the film "Christmas Lovers Anonymous" (released November 2021)* Welcome home to this fully renovated vacation rental in downtown Hudson, WI. This immaculate home is just blocks from the St. Croix River, and the fun shops and restaurants in historic downtown Hudson. This home was remodeled specifically to host travelers. Every effort has been made to provide guests with the comforts of home. Check out my other 5-Star Hudson property on River Street! County Permit ID# LDGA-BDQRRV

Modern Cozy Suite w/ Kitchen & Private Entrance
Discover an ideal retreat in this well-designed suite. Unwind on a plush queen Casper bed for a restful night. Indulge in a luxurious full bath with complimentary bathrobes, stunning floor-to-ceiling tile and heated floors. Start your day with freshly brewed coffee in a fully equipped kitchen, featuring a stove, oven, microwave, tea kettle, and a spacious fridge with a freezer. Explore the beauty of White Bear Lake, one of the Twin Cities largest lakes. This Airbnb stay is sure to be memorable.

The Writers Cabin-Sauna/hot tub/river access
Welcome to the writers cabin at wilder retreat on the saint croix. A place to unplug and unwind to connect more, and experience the healing power of nature. The cabin/tiny house is well appointed and designed for beauty and comfort. Enjoy access to the river as well as our wood fired sauna and wood fired hot tub. Equipped with a queen sized bed in the loft, cooktop, solar power, and a pump sink. A gas fireplace keeps you warm in the winter. We invite you to come and rest, and leave restored.

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.

The Retreat on Randolph a modern upper duplex unit
Stylish upper duplex unit newly renovated with private outside entry and street parking. Trader Joe's, restaurants, liquor store and other amenities within walking distance. Closely located to the airport, numerous colleges/universities, Allianz Field, Xcel Energy Center, Grand Avenue, Mall of America, St. Paul and Minneapolis venues. Features a full kitchen, bedroom, separate office area, washer/dryer, dining/living room, fiber optic Wifi, Smart TV with access to your favorite apps.

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.

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!
Popular amenities for May vacation rentals
Other great vacation rentals in May

Historic Loft Right on Main St

Lakefront Charm: Your Cozy Studio Escape!

Treetop Apartment

Lone Loon Lakehouse (The Triple L) @ Big Marine

Whimsical Cozy Lakeside Retreat

Unity Farm-The Roost/stargazer cabin/river access

The Lil Suite of Historic Stillwater.

Chic 2BR/2BA with Stunning Views & Laundry
Destinations to explore
- Upper Peninsula Vacation rentals
- Platteville Vacation rentals
- Minneapolis Vacation rentals
- Wisconsin River Vacation rentals
- Milwaukee Vacation rentals
- Twin Cities Vacation rentals
- Madison Vacation rentals
- Lake Geneva Vacation rentals
- Thunder Bay Vacation rentals
- Wisconsin Dells Vacation rentals
- Duluth Vacation rentals
- Green Bay Vacation rentals
- Uptown
- Target Field
- Lake Elmo Regional Park Reserve
- US Bank Stadium
- Minnehaha Falls
- Treasure Island Resort & Casino
- Nickelodeon Universe
- Trollhaugen Ski Area
- Xcel Energy Center
- Valleyfair
- Minneapolis Institute of Art
- Wild Mountain
- Stone Arch Bridge
- Afton Alps
- Interstate State Park
- Guthrie Theater
- Walker Art Center
- Minnesota History Center
- Buck Hill
- Minneapolis Scupture Garden
- Target Center
- Minneapolis Convention Center
- The Armory
- Mystic Lake Casino




