
Holiday rentals in May
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Top-rated holiday rentals in May
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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
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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.
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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. 😃
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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.
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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.
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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.
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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
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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.
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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
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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.
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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!
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Historic Home w Modern Updates Near Taylor's Falls
Cascade House has all the charm you could ask for in a historic house, and all the updates you need to stay cozy and comfortable. With a fireplace, office, and plenty of living space, you may never want to go out. But if you decide to venture out, Cascade House is just blocks from shops and restaurants in historic downtown Osceola, and minutes from hiking at national and state parks, kayaking, canoeing, skiing and ropes courses, and even ATV/Snowmobile trails.
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Popular amenities for May holiday rentals
Other great holiday rentals in May

Spacious Lake Stay, Easy Drive!
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Stillwater retreat
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Luxury Lakefront Retreat | Beach + Private Chef
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Somerset “La Casita”in the Pines & Peacocks
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Stone's Throw from St Croix & Downtown Stillwater
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Charming Lake House Sleeps 19
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Dockside Cottage on Forest Lake
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Cottage in the Alley, River View, Stillwater, MN
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Destinations to explore
- Minneapolis Holiday rentals
- Milwaukee Holiday rentals
- Des Moines Holiday rentals
- Saint Paul Holiday rentals
- Duluth Holiday rentals
- Sioux Falls Holiday rentals
- Wisconsin Dells Holiday rentals
- Thunder Bay Holiday rentals
- Madison Holiday rentals
- Marquette Holiday rentals
- Lake Geneva Holiday rentals
- Green Bay Holiday rentals
- Mall of America
- Target Field
- US Bank Stadium
- Xcel Energy Center
- Minnehaha Falls
- Target Center
- Lake Nokomis
- Nickelodeon Universe
- Minneapolis Convention Center
- Valleyfair
- Interstate State Park
- Trollhaugen Ski Area
- Afton Alps
- Wild Mountain
- Mystic Lake Casino
- The Armory
- Macalester College
- Minneapolis Institute of Art
- Stone Arch Bridge
- Como Park Zoo & Conservatory
- Walker Art Center
- Lake Harriet Bandshell
- Cathedral of St Paul
- Minnesota State Fair





