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Osceola Holiday Rentals

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Holiday Rentals in Osceola

Hudson Inn & Suites
3.0 star property
8.2 out of 10, Very good, 566 reviews
"Spacious room, very clean, and quiet. I will most likely stay here again in my next visit to Hudson, WI."
The price is NZ$168
per night
4 Jun - 5 Jun
Hudson Inn & Suites
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
9.4 out of 10, Exceptional, 29 reviews
"I stayed for an extended period of time. The owner and his sons live on the property, but you won’t see them very much. The property is SO peaceful, quiet, and safe. They’ve been working to improve it and so there’s some renovations and things here and there, but nothing that would make you uncomfortable or disturb you. My kids were welcomed here, and the family even helped me through an epic flat tire crisis. They have literally everything you need and then some as far as kitchen, bathroom,...
The price is NZ$172
per night
4 Jun - 5 Jun
Hideaway From The Twin Cities: 5 Bdrms: East'n Sky, N ⭐,Sunset, Exprs, Bird Nest
Romantic getaway! With gorgeous views from the Hot Tub!
9.4 out of 10, Exceptional, 73 reviews
"This place was quiet and a perfect get away. "
The price is NZ$498
per night
4 Jun - 5 Jun
Romantic getaway! With gorgeous views from the Hot Tub!
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All seasons cabin getaway
10.0 out of 10, Exceptional, 33 reviews
"The leaves were exploding in color during our stay at Balsam Lake. The cabin was everything we needed for a relaxing getaway. Quiet, comfortable and beautiful. We brought our canoe to explore the lake and we found some lovely wineries/breweries nearby. We would absolutely stay again!"
All seasons cabin getaway
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
9.6 out of 10, Exceptional, 29 reviews
"Enjoyed our stay, just what we needed for Mother’s Day. Steve the owner was great and attentive! Thanks and we will stay again!"
The price is NZ$172
per night
4 Jun - 5 Jun
Hideaway from the Twin Cities: 5 single rooms w/home use, 2 adult price 80/rm.
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
9.4 out of 10, Exceptional, 28 reviews
"Very clean. Nice warm place to stay and close to local bars for a nice dinner. Will stay again."
The price is NZ$313
per night
10 Jun - 11 Jun
Beautiful Balsam Lake home with Jacuzzi tub close to Lake and park
Log Cabin, Lake Retreat
9.6 out of 10, Exceptional, 62 reviews
"Very cozy log cabin with everything one would need. Beautiful views and close to town for supplies. Had a great time and would definitely come back!"
Log Cabin, Lake Retreat
Gathering families, friends, & coworkers
10.0 out of 10, Exceptional, 19 reviews
"a group of old friends stayed for a weekend to play board games and reconnect. The sanctuary was the perfect match for space and sleeping arrangements. Thanks!"
Gathering families, friends, & coworkers
Cheerful lake house close to skiing, state parks, wine tasting, and much more
9.4 out of 10, Exceptional, 6 reviews
"The cabin had lots of room for sleeping, only downfall was there was not any space to play yard games."
Cheerful lake house close to skiing, state parks, wine tasting, and much more
Stillwater's Third Street Inn
10.0 out of 10, Exceptional, 187 reviews
"We had a great stay! The house is very close to everything downtown! Everything with checking in and checking out went smooth and was very easy. It was a very clean and nice place to stay on our trip to Stillwater!"
Stillwater's Third Street Inn
River road cabin
8.8 out of 10, Excellent, 8 reviews
"Me and some friends spent the night here during a weekend road trip. We loved the cozy interior, easy check-in and check-out process. The living room is spacious and the smart TV was a great thing to have. I would definitely recommend!"
The price is NZ$340
per night
4 Jun - 5 Jun
River road cabin
Less then 2 miles from downtown Stillwater
8.4 out of 10, Very good, 10 reviews
"Very clean, hallway to the apartment is kind of grungy. Accommodations were well represented."
Less then 2 miles from downtown Stillwater
Nordic Harbor Haus
Nordic Harbor Haus
Historic Stillwater Home close to downtown
10.0 out of 10, Exceptional, 20 reviews
"Cozy, clean house in a great location. We enjoyed our stay!"
The price is NZ$603
per night
5 Jun - 6 Jun
Historic Stillwater Home close to downtown
Bayport's Charming Tree House
The price is NZ$697
per night
4 Jun - 5 Jun
Bayport's Charming Tree House
Lakefront Cottage 2 min to downtown
10.0 out of 10, Exceptional, 14 reviews
"My husband and I and my two pups booked a 4 day weekend for one last summer hurrah 9/29 through 10/2. Property was as described, location was perfect, sunrises and sunsets were beautiful. It was very peaceful as no other cabins were occupied except our host Debbie! Thank you for a wonderful get away Debbie - your property was well-maintained and lovely for our needs."
Lakefront Cottage 2 min to downtown
Cottage on the lake near downtown Stillwater
10.0 out of 10, Exceptional, 226 reviews
"It was a wonderful experience, the house was an accurate listing, clean and when we had a small issue with a beeping noise in the house on arrival the host was prompt in replies. Came very quickly and was extremely friendly dealing with it! Would definitely stay here again!"
Cottage on the lake near downtown Stillwater
Beautiful cabin getaway on Green Lake
10.0 out of 10, Exceptional, 127 reviews
"We had a lovely long weekend. The kids enjoyed the swing, the big beach, and they thought the bunk beds were fun. The property was fully stocked with anything you’d want, clean, comfortable, and good water pressure. It was a bit rainy for our trip so we spent a couple days at the mall of America. On the nice days it was easy fishing right off the dock. Plus you are in a quiet part of the lake that was easy for paddle boarding/kayaking, but big enough to take the kids tubing if you choose to...
Beautiful cabin getaway on Green Lake
Overlooks St. Croix River Crossing
10.0 out of 10, Exceptional, 144 reviews
"Third time here and not disappointed. Louise and Martin are great hosts. Just a short drive to downtown Stillwater and all the shops and restaurants. Will be back!"
Overlooks St. Croix River Crossing
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
9.4 out of 10, Exceptional, 80 reviews
"Great stay, place, and location! We had a blast and will definitely be back. Thank you!"
MainStreetLocation|GirlsNight|Families|Pets|FoodMusicShopArtExploreBikeFunPlay!!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Osceola you may be interested in

Country Inn & Suites by Radisson, Forest Lake, MN
2.5 star property
8.0 out of 10, Very good, 690 reviews
"Nice clean room early check in"
The price is NZ$169
per night
18 Jun - 19 Jun
Country Inn & Suites by Radisson, Forest Lake, MN
Hotel Crosby
2.5 star property
9.4 out of 10, Exceptional, 675 reviews
"Great hotel. Awesome bourbon bar! Very accommodating to our group."
The price is NZ$510
per night
17 Jun - 18 Jun
Hotel Crosby
Comfort Inn & Suites St. Paul Northeast
2.5 star property
8.2 out of 10, Very good, 1,001 reviews
"Good place to stay "
The price is NZ$208
per night
9 Jun - 10 Jun
Comfort Inn & Suites St. Paul Northeast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osceola holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osceola. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Osceola. Seeing all the best attractions is bound to make you fall in love with Osceola. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Osceola short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Osceola?

Yes, there are holiday rentals close to the most popular sights in Osceola, or you can select a more secluded option if you're looking for a relaxing stay. Osceola is known for its riverfront and bars. Make sure you have time to check out the waterfalls and entertainment choices during your trip.

How many holiday rentals are there in Osceola?

Choose from 3 Expedia holiday rentals in Osceola for a memorable holiday.

What can I see and do in Osceola?

Saint Croix River and Apple River are a couple of lovely local spots to get outside and enjoy nature. Osceola & St. Croix Valley Railway and Trollhaugen are other places to visit while you're in town.

What are holiday rentals like in Osceola?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osceola. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

Recent reviews of Osceola properties
Expedia verified reviews