
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.

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!

Cozy Cabin on Big Marine Lake
Cozy renovated cabin on the west bay of Big Marine Lake. Launch your speedboat or pontoon at the public access on the north end and spend your day boating, tubing or water skiing. Need a break? Tie off on your private dock and use the stand up paddle boards or kayak your way to the sand bar. Big Marine Lake is one of the nicest, cleanest swimming & fishing lakes in the Twin Cities metro area. Get away without spending hours in the car! This cabin is perfect for a family of four or two couples.

Peaceful and Private Stillwater Chalet On Water
As you venture down the woodsy driveway of the Stillwater Chalet, you may notice your blood pressure seems to have lowered and your shoulders feel a little lighter. You have entered a private waterfront refuge in the historic town of Stillwater, with downtown 3 miles away. Sip coffee and take in the panoramic view of the backyard pond, play lawn games, and explore the glossy water by kayak. End your day with a relaxing steam shower and an evening beverage around the fire pit under the stars.

Somerset “La Casita”in the Pines & Peacocks
Take it easy at this unique and tranquil getaway. Enjoy this cozy space with in-floor heat, gas fireplace and charming decor. Set in the pines with walking trails, pet friendly, motorcycle friendly-ATV trails, private patio, fire pit (wood provided). Close to everything Somerset has to offer, the Apple River, Amphitheater, Cedar Lake Speedway, , and more. Conveniently located between Stillwater, Hudson, New Richmond and Osceola.The Casita is cozy and charming with a Costa Rican vibe

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.

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.

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.

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.

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!

Star Gazing Glass House 4 Season with Hot Tub
This glass house has a mini split offering both heat and air conditioning. There is something truly magical about being submersed in nature. Watching beautiful snowflakes cascade around its walls, snuggled under heated blankets while star gazing. Rainstorms have a new meaning, sunsets and sunrises become a life-changing experience. This is a photographer's dream, a romantic getaway, or the perfect place to reconnect with yourself. Private hot tub and fire pit.

Yurt-Style Tent at Stone Creek Farm
1 of 4 campsites on the farm, this yurt-style tent has all you need to enjoy camping without the work! The campsite includes a picnic table, BBQ grill and fire pit. There is a self composting toilet on site. Camp carts available to bring gear out. Drinking water is available from the hose out by the high tunnel. It is about a quarter mile walk to the site. If this site is booked when you want to stay, check out our new sites Peachy Keen and Plum Perfect!
Popular amenities for May vacation rentals
Other great vacation rentals in May

The Boat House

Cute cabin on the Appleriver #3

Treetop Apartment

The Fox Den: Comfy Farmhouse Lower Unit

Pebble on the Bay

Bright & Comfy Stillwater Loft Apartment

Cozy Downtown WBL Cottage one block away from lake

Spacious Lake Stay, Easy Drive!
Destinations to explore
- Minneapolis Vacation rentals
- Milwaukee Vacation rentals
- Des Moines Vacation rentals
- Saint Paul Vacation rentals
- Duluth Vacation rentals
- Sioux Falls Vacation rentals
- Wisconsin Dells Vacation rentals
- Thunder Bay Vacation rentals
- Madison Vacation rentals
- Lake Geneva Vacation rentals
- Marquette Vacation rentals
- Green Bay Vacation rentals
- Mall of America
- Target Field
- US Bank Stadium
- Xcel Energy Center
- Minnehaha Falls
- Target Center
- Nickelodeon Universe
- Minneapolis Convention Center
- Trollhaugen Ski Area
- Lake Nokomis
- Valleyfair
- Interstate State Park
- Allianz Field
- Wild Mountain
- Afton Alps
- Minneapolis Institute of Art
- Mystic Lake Casino
- The Armory
- Macalester College
- Stone Arch Bridge
- Walker Art Center
- Guthrie Theater
- Como Park Zoo & Conservatory
- Lake Harriet Bandshell





