Holiday rentals 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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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.

Guest house in Stillwater

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

4.97 out of 5 average rating, 145 reviews

Guest favourite

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

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

4.85 out of 5 average rating, 698 reviews

Top guest favourite

An inviting rooftop deck features comfortable seating with decorative cushions, surrounded by potted greenery. Soft lighting from string lights creates a cozy atmosphere, while panoramic views of the St. Croix River and downtown buildings are visible in the background.

Townhouse in Stillwater

Lumberjack Inn DT-on Main St. with a rooftop deck

Welcome to our unique townhome located in a historical building nested into the heart of downtown, offering panoramic views of the St.Croix River.Unwind on the expansive rooftop deck, enjoying a 360 panoramic view of the river, downtown, and the charming historical neighborhood.This gem is also apart of the Union Art Alley, featuring a vibrant mural by a local artist.With dining, shopping, and live entertainment just steps away, your stay promises a perfect blend of culture and entertainment.

4.96 out of 5 average rating, 153 reviews

Top guest favourite

Home in Stillwater

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.

5.0 out of 5 average rating, 52 reviews

Top guest favourite

The living room features large windows allowing soft natural light to brighten the space. A cozy seating arrangement includes two black armchairs and a spacious gray sofa. A central round coffee table is complemented by a decorative piece, and a small side table is positioned beside the sofa.

Home in Hudson

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.

5.0 out of 5 average rating, 134 reviews

Guest favourite

Home in Stillwater

Historic Stillwater Haven- flexible check in/out

Your family will be close to everything when you stay at this peaceful, charming, centrally-located home. Enjoy everything the charming City of Stillwater has to offer. Perfectly located on the South Hill- just a 10 min walk (0.75 mi) from Downtown! Ride on the Stillwater River Boats or simply enjoy a stroll across the historic Bridge. You can enjoy hiking, sight seeing, restaurants and relax in the St. Croix valley- approx 30mins away from all that the Twin Cities has to offer. Welcome!

4.92 out of 5 average rating, 26 reviews

Top guest favourite

The spacious living area features exposed brick walls and high ceilings. Two white sofas are arranged around a decorative area rug, with a wooden coffee table at the center. A television is positioned on a light-colored media unit near large windows allowing natural light to illuminate the space.

Loft in Stillwater

Historic Loft Right on Main St

** Hi! Thanks for considering my place! Be sure to read through my entire listing to ensure you enjoy your visit! Come discover Stillwater and all it has to offer in a spacious and updated historic loft right on Main St. You will love the short walk home with a belly full of the delicious food and drinks that Stillwater is known for, especially after perusing the amazing art galleries, boutique clothing stores, endless antiques, and historic candy shops all right outside your front door.

5.0 out of 5 average rating, 75 reviews

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.

Guest house in Stillwater

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” for a burger-n-beer, fresh baked goods, & brunch. Go out and enjoy the St. Croix Valley in all it has to offer, including the St. Croix River, great restaurants, shopping, sightseeing, and so many outdoor activities. Or stay home and...just relax.

5.0 out of 5 average rating, 129 reviews

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

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.

4.99 out of 5 average rating, 210 reviews

Superhost

Home in Bayport

Stillwater, MN Riverfront Home & Dock

Located 5 minutes from downtown Stillwater, MN, this private riverfront home sits on 2+ acres along the St. Croix River. Enjoy nearby Stillwater shops, dining, and riverfront attractions. With 200+ feet of shoreline and a private dock for boating and fishing, this updated 4BR, 3BA home sleeps 12—perfect for families, wedding parties, and large group getaways. Relax with beach access, fire pit, grill, and outdoor dining. Minutes to Hudson and 25 minutes to the Twin Cities.

5.0 out of 5 average rating, 3 reviews

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

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!

5.0 out of 5 average rating, 147 reviews

Guest favourite

A modern kitchen area features stainless steel appliances and white cabinetry. A large island with bar stools provides workspace, while a dining table with a bench and chairs accommodates meals. Decorative lighting fixtures enhance the room's ambiance against deep grey walls.

Flat in Hudson

Modern Apartment steps to everything downtown

Beautiful, modern 2 bedroom apartment in Downtown Hudson. The entire apartment provides everything you will need. A fully equipped kitchen, laundry, soaking tub, wifi etc... There is a King Bed, Queen Bed and sofa to sleep 5. Steps to Hudson's best coffee shops, restaurants, bars, patios, and shopping. Enjoy a stroll along the St. Croix River. This location is perfect for families, couple getaways, corporate rentals or friend getaways.

4.89 out of 5 average rating, 262 reviews