Holiday rentals in May

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Top-rated holiday rentals in May

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

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Guest favourite
The spacious living area features exposed brick walls and hardwood floors. A white sofa is positioned near a flat-screen television, with large windows allowing natural light to fill the room. A door leads to the outside, and a cozy area rug is beneath the seating arrangement.
Loft in Stillwater
4.86 out of 5 average rating, 652 reviews

Downtown Lift Bridge Loft

Located in the heart of downtown Stillwater, Lift Bridge Loft is an absolutely gorgeous space with exposed brick and stone and hardwood floors. You will feel right at home while enjoying the unsurpassed view of the St. Croix Valley! Walking distance to restaurants, coffee shop right downstairs, antique malls, candy shops, bike/walking paths (including the loop connecting the two bridges), and much more! NO PARTIES OR EVENTS ALLOWED! License number STHR 2018-07 Security cam outside, stay off roof

Top guest favourite
A charming white guesthouse is framed by vibrant purple flowers and green grass. Skylights are visible on the roof, and large glass doors create an inviting entrance. Surrounding landscaping adds to the appeal, offering a welcoming view of the property.
Guest house in Stillwater
5 out of 5 average rating, 104 reviews

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.

Top guest favourite
Guest house in Stillwater
4.97 out of 5 average rating, 129 reviews

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

Top guest favourite
Guest suite in Osceola
4.96 out of 5 average rating, 269 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 favourite
Place to stay in Saint Croix Falls
4.95 out of 5 average rating, 397 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 favourite
The living area features two gray sofas arranged around a circular coffee table. A television is situated on a wooden console, while vibrant artwork adorns the walls. Light streams in from a window, creating a bright atmosphere. Metal lockers provide additional storage.
Guest house in Stillwater
4.98 out of 5 average rating, 135 reviews

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!

Top guest favourite
Home in Hudson
4.99 out of 5 average rating, 221 reviews

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

Top guest favourite
Guest suite in White Bear Lake
4.99 out of 5 average rating, 135 reviews

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.

Top guest favourite
A charming two-story house features a light green exterior with white trim. A covered front porch offers a welcoming entry. Large windows provide natural light and a view of the surrounding lawn, which is neatly landscaped with green grass and a few trees.
Home in Northeast Minneapolis
4.94 out of 5 average rating, 123 reviews

Northeast Oasis with Hot Tub

Welcome to your cozy retreat in Northeast Minneapolis! This charming two-bedroom home captures the essence of the neighborhood with its unique decor and warm atmosphere. The living area is inviting, perfect for relaxing after a day of exploring. The fully equipped kitchen makes meal prep a breeze, while the dining space offers fun & functionality. Step outside to unwind in the private hot tub under the stars, surrounded by the local charm—ideal for a romantic getaway or small family retreat!

Top guest favourite
A light-filled dining area features a round table surrounded by four chairs, with a large plant nearby. An elegant mirror reflects the space, while a kitchen area showcases sleek appliances. The warm wood flooring complements the modern, neutral decor throughout the room.
Flat in Highland
4.99 out of 5 average rating, 246 reviews

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.

Top guest favourite
The exterior of a two-story home is presented, featuring a combination of siding and stone accents. A spacious driveway leads to a double garage, while a clear blue sky complements the structure. A water tower is visible in the background amidst trees.
Flat in Forest Lake
5 out of 5 average rating, 114 reviews

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!

Top guest favourite
Home in Dayton's Bluff
4.99 out of 5 average rating, 112 reviews

Comfy St Paul Duplex-close to downtown, EZ parking

Welcome to this sunny, upper level duplex unit located just across from downtown Saint Paul in historic Dayton's Bluff. Conveniently located, it is under 2 miles to RiverCentre, 1 mile to CHS Field, St Paul Farmers Market or Union Depot, just .4 miles to Metro State University & a few blocks to Mounds Park & Bruce Vento Nature Sanctuary. This spacious, city retreat offers relaxing work spaces, a yoga/fitness room, and coffee, tea and snacks to help make your stay comfortable.

Popular amenities for May holiday rentals

  1. Airbnb
  2. United States
  3. Minnesota
  4. Washington County
  5. May