Holiday houses 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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Top Guest favourite
A charming treehouse is nestled among the lush branches of a large, mature oak tree. The wooden structure features multiple levels with a spacious deck that connects to the main entrance, surrounded by greenery, creating a serene and natural environment.
Home in Cottage Grove
4.98 out of 5 average rating, 732 reviews

Tree House Luxury Stay

Perched high in the majestic arms of a 150 year old Burr White Oak tree. This cozy 1200 square foot, seven-room house not only has breathtaking views it also has enchanting and delightful surprises befitting of a fairytale. Climb 40 feet up onto the Observation Tower, where a telescope waits for you, ready to scan the night sky, and reveal the panorama of the heavens -- overlooking 500 acres of natural splendor right next door. Step into the hot, bubbling jets of the jacuzzi, or warm caress of the rain shower, and restore your spirits by soothing your muscles, melting away any residual tensions of the day. Get a restful sleep in one of our soft beds. In the morning, pad around on in-floor radiant heated floors (so cozy during winter-time.) Or enjoy your morning coffee on one of four outside decks. And don’t forget to solve the mystery of the Treehouse, that awaits your discovery within its wood beamed walls. This treehouse was custom designed by its architect with three dimensional chess in mind. Artisan architectural details are found throughout. Crystal chandeliers bedeck its high ceilings, and marble countertops grace the elegant, fully appointed kitchen. (A surround sound system helps set the mood for those special dinners in the dining nook.) One of two fireplaces adds luxurious touches to the primary bedroom with a queen bed, and hideaway bed in the secret room, along with a jacuzzi and rain shower in the primary bath, as well as a second bathroom in the secret room. Perfect for honeymooners, couples, business/corporate overnights, solo travelers and families with children over twelve years old. These are only a few of the many luxury details in this spectacular vacation spot must-see. Spend your days snuggled up beside the fireplace of your choice, while enjoying the panoramic views. You can stream your favorite movies and shows with Broadband Wi-Fi throughout the house. Come down for a leisurely walk around the grounds, and stop by to visit and feed the goats and chickens that call Hope Glen Farm their home in the corral of this historic farmstead. Bring your stress levels down and your heart rate up by walking over to Washington County Cottage Grove Park Reserve, just steps away, and answer its call to explore over 550 acres of fields and forests. Go hiking and biking down its trails, geocaching the hills and ravines for hidden treasures, or spend the afternoon fishing and kayaking in the lakes. And don’t let cooler temperatures keep you from discovering the pristine natural beauty of winter! Winter activities include cross country skiing and snowshoeing on the blankets of snow. Breathe deeply of the crisp Minnesota winter air -- truly one of life’s great pleasures. Plus, only a ten minute drive brings you to nearby Afton Alps in Afton State Park offering downhill skiing and snowboarding. For clarity, the Treehouse has 2 private bedrooms: Bedroom 1 is has a queen bed. Bedroom 2 has a bedroom with standard sofa bed with attached half bathroom, which is the secret room a must find. Give yourself the gift of this luxurious enchanting TreeHouse Suite in the treetops, for a enchanting vacation experience you'll never forget. Something to write home about!

Top Guest favourite
A cozy living area features a modern gas fireplace beneath a flat-screen TV. A leather chair with a side table is positioned next to a low coffee table, while a large window allows natural light to fill the space. A sliding glass door leads to an outdoor deck.
Guesthouse in Stillwater
4.97 out of 5 average rating, 132 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
A light-filled living space features a comfortable leather sofa, a wooden coffee table, and a flat-screen TV mounted on a wooden cabinet. A round dining table with two chairs is positioned near the window. Decorative horse-themed accents are visible on some furnishings.
Guest suite in Osceola
4.96 out of 5 average rating, 279 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
A cozy tiny home is illuminated at night, revealing warm light from its windows. A stone pathway leads to an inviting front deck surrounded by greenery. Nearby, a decorative lantern can be seen in the foreground, enhancing the serene ambiance.
Tiny home in Saint Croix Falls
4.92 out of 5 average rating, 272 reviews

Wolf Creek Luxury Eco-Tiny Home on the Ridge

Experience our custom-built eco-friendly tiny home perched on the top of the ridge above the majestic St Croix River Valley. Enjoy expansive views from the deck, loft or many windows looking over the valley. Enjoy our private barrel-sauna, fire-pit, gas grill, pond with canoes and kayak or Wolf Creek with a private crystal-clear swimming hole! Or just chill on the ridge watching the many birds and wildlife. Just over an hour drive from the Twin Cities, a romantic and memorable stay awaits you!

Guest favourite
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
4.9 out of 5 average rating, 219 reviews

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.

Top Guest favourite
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
4.98 out of 5 average rating, 128 reviews

Lake House Retreat: Modern, Stylish, Arty, Fun

Secluded modern design, fun, stylish, lakefront retreat carefully nestled in mature pines on 2.5 acres with 120 feet of easily accessible shoreline and large spa for year-round activities. For families, groups, and pets on a countryside neighborhood. Indoors and outdoors are connected with careful positioning of many large windows, sliding doors, patio and rooftop deck. For a closer look at the design, seasonal moments, and behind-the-scenes details, find us @StaysInColor.

Top Guest favourite
Guest suite in Stillwater
4.98 out of 5 average rating, 176 reviews

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.

Top Guest favourite
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
5 out of 5 average rating, 132 reviews

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!

Guest favourite
A glass house reflects natural surroundings, enclosed by trees and sunlight. The interior features a spacious bed draped in white linens, with cozy seating visible nearby. A wooden deck extends outwards, complemented by outdoor furniture and decorative lanterns.
Dome in Afton
4.87 out of 5 average rating, 409 reviews

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.

Top Guest favourite
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
4.96 out of 5 average rating, 246 reviews

Heirloom Cottage | Private Retreat Hot Tub & Sauna

A 1920s cottage on 1.2 wooded acres, just north of the Twin Cities. 15 minutes from downtown Minneapolis or St. Paul, but it feels a world away. Fireside sitting room, sunroom with a hanging swing and sunrise views, full kitchen, and a glass-walled backyard studio. Outside: fire table, hot tub, sauna and string lights on the deck. Sleeps 10. Built for getaways, friend trips, and anyone who could use a good exhale. Come rest.

Guest favourite
A newly remodeled blue cottage is set against a backdrop of lush greenery. The entrance features a set of stairs leading to a welcoming porch. Natural stone landscaping and decorative plants complement the exterior, with gravel pathways visible in the front yard.
Home in Stillwater
4.78 out of 5 average rating, 219 reviews

Cozy 2-Bedroom Stillwater Retreat

Welcome to The Guesthaus on Maple! A brand-new listing in beautiful Stillwater, Minnesota, this home is completely remodeled. Appliances and furniture are brand new! This idyllic retreat is perched upon a hill with a view of Lake McKusik. The quiet street connects with walking trails around the lake. Pets welcome. License #2023-02

Top Guest favourite
The barn-style building features a rustic wooden exterior with a green metal roof. A balcony is visible on the upper level, while a manicured lawn with flower beds surrounds the structure, inviting guests to enjoy the natural setting.
Barn in Afton
4.99 out of 5 average rating, 152 reviews

The Loft at Strawberry Hill Farm

Welcome to comfort and relaxation! Exquisite rural setting in the river valley of the St Croix. Cozy up in this new barn apartment on our property that is close to beautiful parks and trails and many attractions and also a half hour from the twin cities.

Popular amenities for May holiday rentals

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