Holiday houses in Oak Park Heights

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Top-rated holiday rentals in Oak Park Heights

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

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A spacious living area features a white sectional sofa positioned around a wooden coffee table. Textured walls in exposed stone and wood accents create a warm backdrop. Soft area rugs are laid over hardwood floors, enhancing comfort and inviting relaxation.
Loft in Stillwater
4.85 out of 5 average rating, 679 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
The spacious sleeping area features a king bed dressed in white linens, complemented by soft pillows. A circular lounge chair sits nearby on a decorative area rug. Natural light filters through multiple skylights and windows, highlighting the modern, airy design.
Guesthouse in Stillwater
5 out of 5 average rating, 117 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
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, 134 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
An aerial view showcases a rural property featuring multiple buildings, including a large red barn, a farmhouse, and a smaller structure. Lush greenery surrounds the area, with trees and an open field visible. Pathways connect the buildings, creating an inviting outdoor space.
Farm stay in Cottage Grove
4.95 out of 5 average rating, 587 reviews

Luxury Barn Cottage and Villa at Hope Glen Farm

The Corn Crib Cottage Barn or Villa is a luxurious and rustic 1100 square foot space. The Corn Crib originally used to dry corn and animal housing. This is a very rare historical building built in the 1920's The villa has a 2 person whirlpool jacuzzi , rain shower, beautiful full kitchen, fireplace and next to the 550 acre Washington County Cottage Grove Ravine regional park reserve. The Cottage is near the famous lofty lodge treehouse in the area. Treehouse on airbnb listing number 14059804

Top Guest favourite
The charming chalet is framed by tall trees, with a wooden deck overlooking the serene pond. A patio area features a metal table surrounded by chairs, adorned with vibrant flowers. The rustic building showcases large windows, blending harmoniously with the natural surroundings.
Home in Stillwater
5 out of 5 average rating, 45 reviews

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.

Top Guest favourite
A single-story home is framed by lush greenery and flowering shrubs. The entrance features a decorative door and stone accents, while a well-maintained lawn leads to the front. The surrounding trees provide a natural setting, enhancing the peaceful environment.
Guest suite in Stillwater
4.98 out of 5 average rating, 184 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, 137 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, 414 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 cozy great room features a sectional sofa in neutral tones, complemented by decorative pillows. A smart TV is mounted on the wall above a modern fireplace. Stained glass windows allow soft light to fill the space, which is anchored by a patterned area rug.
Apartment in White Bear Lake
4.96 out of 5 average rating, 124 reviews

Garden Level @ The Lake Hideaway, downtown WBL

Enjoy a stylish experience at this centrally-located place in downtown White Bear Lake. Steps away from our most popular bars and restaurants: Washington Square, Brickhouse, and Big Wood Brewery. Moments away from Lake Ave and the Mark Sather walking and biking trail. The Lake Hideaway is nestled in White Bear's historic downtown. Located on 3rd Street in Hardy Hall (est. 1889). Enjoy a touch of history and unique art deco flare in your retreat.

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
4.95 out of 5 average rating, 254 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
An outdoor seating area features a fire pit surrounded by log seating, with flames illuminating the space. A patio with string lights overhead creates a cozy setting. In the background, a glimpse of a vehicle is visible, along with a well-maintained lawn.
Home in Stillwater
4.89 out of 5 average rating, 38 reviews

Stillwater retreat

Our renovated residence is tucked away in a quiet neighborhood located 5 minutes from downtown Stillwater and downtown Bayport. Have an eventful day exploring the river and trails, make s’mores by the bonfire, or simply relax. We are here to earn your business and make sure you have a wonderful stay. Boat trailer can be tucked away beside garage; St. Croix public access is 1mi away.

Top 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
4.79 out of 5 average rating, 227 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

Popular amenities for Oak Park Heights holiday rentals