Vacation rentals in Osseo

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Top-rated vacation rentals in Osseo

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

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Guest favorite

Home in New Lisbon

5 out of 5 average rating, 35 reviews

Retreat on the Beach! EV Friendly! Hot tub!

LuzRating, 5 stars3 weeks ago

Me and my family enjoyed are time at the lake house. Can’t wait to comeback and hopefully we have more time to explore the area and more activities since it was raining most of the time. Overall the house felt like home. Highly recommended this lake house. Thank you to the host for all the help.

Guest favorite

Home in Frontenac

4.9 out of 5 average rating, 58 reviews

Charming 3 bed/3bath renovated cabin on Lake Pepin

LisaRating, 5 stars1 month ago

Amazing views, great natural light, well equipped kitchen, comfy beds and updated bathrooms. Enjoyed the relaxing atmosphere and Adirondack chairs on the sandy shoreline watching the wildlife. Super close to Lake City and Frontenac State Park and just a short drive to Red Wing-this is a great spot for exploring the towns, taking a hike or just relaxing at this beautiful spot and home.

Guest favorite

Home in Chippewa Falls

4.94 out of 5 average rating, 32 reviews

Dockside at Wissota

NicoleRating, 5 stars1 week ago

Our group was celebrating my sister’s bachelorette weekend, and we could not have picked a better place or host. The place was perfect for our group and Linda has thought of everything. Linda had great communication and was thoughtful with all touches. Would highly recommend staying here! Thank you, Linda!

Top guest favorite

Home in Chippewa Falls

4.98 out of 5 average rating, 105 reviews

Sunsetters - Good Vibes Lakeside Lodge

JeffreyRating, 5 stars1 month ago

Colleen was an amazing host. She was easy to communicate with, and typically responded to messages within 30 minutes. She was very accommodating and went above and beyond to make our stay comfortable and memorable. We are a family of 9 adults and 4 small children that live in Washington; and met in Chippewa Falls to celebrate our son's 31st birthday. Colleen's Airbnb was absolutely beautiful, and the perfect place for a family gathering. It's hard to put into words how lovely this home and property were. Everything about this home was high end: the kitchen was complete with every possible appliance ; the finishings and furniture were tasteful and high quality; the beds were very comfortable with nice linens and comforters. The 4 bathrooms all had showers/tubs. The setting of the home was lovely, and the lake was a beautiful backdrop for our time spent inside and out. We enjoyed the fire pit, the playset and walking on the frozen lake. I would highly recommend this Airbnb!

Guest favorite

Cabin in Warrens

4.93 out of 5 average rating, 27 reviews

Unique Privately Owned - Near UTV trails/waterpark

LaneyRating, 5 stars3 months ago

Natasha was very responsive. Her place had all the extras which was really nice not to have to pack, dish soap, dishwasher detergent, towels, crockpot, pots/pans, pizza cutter, etc. Very close to 3 bears, so quick walk across the street (in the resort neighborhood) to the Waterpark!

Top guest favorite

Home in New Lisbon

5 out of 5 average rating, 35 reviews

Lakehouse on Beach Lake w/Hot Tub & Screened Porch

AkaviaRating, 5 stars1 month ago

Myself & 10 friends stayed here for 2 days for my birthday & everything was great! Pam responded fast & accommodated me with early check in/late check out. The house was beautiful & looked exactly like the pictures! Will be booking again for sure!

Superhost

Cabin in Warrens

4.86 out of 5 average rating, 57 reviews

Cheerful 305 Hilltop Cabin near 3 Bears & Trails

JulieRating, 5 stars2 months ago

our stay at Wesley's worked out perfectly for a weekend family reunion. Family came from different directions and we were in the middle. We had opportunity to eat, drinkand be merry to make some great memories. Wesley attentive to my messages and appreciated his input. Thank you Wes and God bless!

Top guest favorite

Home in La Crosse

5 out of 5 average rating, 24 reviews

Luxury Retreat Nestled in Bluffs -10 Mins Downtown

KathrynRating, 5 stars1 week ago

Hidden Hill Retreat was amazing. The house is beautiful with beautiful views. The house is so spacious, we didn't even use the den space in the basement. Tiffany reached out the day of check-in and made it easy to connect of we need anything. 10 out of 10, would recommend!

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What guests are saying

Vacation house

5 out of 5 average rating, 9 reviews8 months ago

We had a great stay. Check in was easy and it was easy to find. The house was clean and nice and peaceful tucked back in the trees. There were plenty of towels int he bathroom. We enjoyed the hot tub and our kids liked the swings and ping pong table, and the bunk beds. It was about 42 minutes from Wisconsin Dells which we frequented. There is a state park nearby that we visited too. I will agree with other reviews to bring lots of bug spray as the mosquitos enjoyed the wooded area as much as we did. Overall a great stay!

Home in Necedah

What guests are saying

Cheerful beautiful home with an amazing lake view.

4.91 out of 5 average rating, 65 reviews1 month ago

Very nice place! It fit our needs for a centrally-located place for a family gathering. We enjoyed our stay very much and would return if the need arises. Within walking disstance of the beach and downtown, along with beautiful views of the lake! The one negative is that the house is located on the main road/highway through town, so traffic noise is pretty much constant. Not terrible, but noticable.

Home in Lake City

What guests are saying

Gorgeous Lakeview Balcony 4 Bedrooms next to pool

4.93 out of 5 average rating, 27 reviews9 months ago

This is one of the best locations at NorthBay Resort. His second floor place is perhaps 100' from the lake and has a spectacular view of the lake and sunsets over the lake. The patio furniture is comfortable. The unit matches the photos and his claims. It has multiple screens but the one in the main room could be a bit larger, however it is adequate. The garage is stocked with bikes and lake toys. The unit had ample supplies. I would stay there again. Do note if you like to eat out and want something other then fried food or bar food the restaurant choices are few and far between. There is a good grocery store in Adams that is about 15 min to the east.

Condo in Arkdale

What guests are saying

Riverview Radiance: 5BR, Scenic Views, Pets OK

5 out of 5 average rating, 31 reviews5 days ago

We like to get together as a family on Easter weekend and really enjoy southeastern MN. The eagle viewing was the best we have ever had! The open concept of the main living area was perfect and what a view while making meals! The home was spotless and had everything we needed. Only wish we could get together more often in the busy lives we have for family weekends to laugh, share meals, take walks, go fishing, enjoy a smore around a fire and take in the wonderful scenery! Big River Escape Grandview was perfect for this!!!!

Home in Minneiska

What guests are saying

Lake Front! Luxury 5 bedroom House with large yard

4.96 out of 5 average rating, 89 reviews1 month ago

Had a great time at Cheryl’s house! It was the perfect house for our girl’s weekend. Lots of space with a large kitchen, and beautiful view of the lake. Loved curling up by the fireplace and chatting at night. So many bedrooms and space for our whole group. We can’t wait to come back in the summer!

Cabin in Merrillan

What guests are saying

Port 19

4.75 out of 5 average rating, 8 reviews8 months ago

This space was perfect for our big group. Plenty of seating and sleeping arrangements for everyone with tons of extra towels, pillows, and bedding. The location is a quiet and private spot along the river with beautiful views. We liked that it was within walking distance from downtown Winona and loved hanging out around a fire at the end of the day. Julie went above and beyond as a host, was easy to communicate with, and flexible with our checkout time so we could spend more time enjoying each other’s company in her great space!

Apartment in Winona

What guests are saying

Vacation condo Eagle View Cottage on Lake Pepin

4.98 out of 5 average rating, 57 reviews6 months ago

We (5 girlfriends) were very pleased with the townhouse and the gorgeous view of the lake, from both the living room and the upstairs bedroom. The place was clean, well stocked with kitchen equipment, bedding, towels and much more. Beautifully decorated for the season (fall) with very comfortable furniture. Thankyou for making our weekend a joy with your hospitality.

Townhouse in Lake City

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Popular amenities for Osseo vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Osseo

Guest favorite

Home in Germantown

4.98 out of 5 average rating, 57 reviews

Multi Family Beach-Lake Home 30 min. From WI Dells

KatrinaRating, 5 stars3 weeks ago

Your place was very wonderful. We had a great time.

Guest favorite

Home in Rochester

4.93 out of 5 average rating, 45 reviews

Come From Away!

KarlieRating, 5 stars4 weeks ago

Jaymi's place was exactly what my family needed. We traveled 7 hours to get there and arrived a bit early. Jaymi was quick to respond to my request for an early check-in, and everything was perfect for our time in Rochester. The finished basement provided a home away from home feel for me and my husband, while my parents were very comfortable on the main level. When you're in Rochester for Mayo clinic appointments having a peaceful place to lay your head at night is important and Jaymi provided everything we needed to be comfortable.

Superhost

Home in Onalaska

4.81 out of 5 average rating, 102 reviews

Backwater hideaway. Big house with water access.

LoriRating, 5 stars2 weeks ago

This place is huge! Three floors of usable space and four large bedrooms plus an office space. It’s very quiet and peaceful with lots of natural light. It is a little far from town but that can be a plus if that’s what you are looking for. It was very family friendly. If you are traveling with someone who has mobility issues, there is a bathroom and bedroom on the main floor but no shower. There was a washer and dryer available for use. I would definitely stay here again. Thanks for the use of your property!

Guest favorite

Cabin in Necedah

4.99 out of 5 average rating, 123 reviews

Little Cabin in the Big Woods - Cabin #2

Deanna JRating, 5 stars2 months ago

This was our second year at the cabin and it was absolutely spectacular! We enjoyed our stay again and appreciate your attention to detail with all the include amenities. Thanks Again, Dee

Guest favorite

Home in Bay City

4.94 out of 5 average rating, 17 reviews

Isabelle Creek Haven - Ultimate Group Getaway

AaronRating, 5 stars2 months ago

Place was secluded and nice space for larger group. Snowed while we were there and very responsive and coming to clear. We were staying with 5 adults and 4 kids skiing at Afton/Welch so the location was good. Didn’t spend anytime checking out the small towns or local sites, but appeared to be plenty of that. Also a nice sledding hill in backyard for kids.

Superhost

Cabin in Warrens

4.86 out of 5 average rating, 28 reviews

Cozy duplex cabin near WI resort and campground

JoelRating, 5 stars8 months ago

We loved that it had 5 bedrooms and 3 bathrooms. everyone had a good bed and no waiting for bathrooms. We played games provided. It was also awesome to have 2 full kitchens. It is plenty close to Three Bears Resort. We bought day passes for our group.

Guest favorite

Home in Mondovi

4.93 out of 5 average rating, 15 reviews

Golf-ATV Trails-Fishing Stream - 1212

RobertRating, 5 stars8 months ago

Always a great place to stay.

Guest favorite

Cottage in Pepin

4.85 out of 5 average rating, 74 reviews

Scenic View Cottage on the Great River Road

KariRating, 5 stars7 months ago

We enjoyed our stay in Pepin. Charlie's cottage was close to everything we were interested in, was very quiet even though off the highway and we appreciated the accommodations.

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Vacation rentals in Osseo

Top-rated vacation rentals in Osseo

Vacation house

Cheerful beautiful home with an amazing lake view.

Riverfront-Sandy Beach-TikiBar-Dock-RecRoom-3700ft

Gorgeous Lakeview Balcony 4 Bedrooms next to pool

Riverview Radiance: 5BR, Scenic Views, Pets OK

Lake Front! Luxury 5 bedroom House with large yard

Luxurious 2 bedroom 2 bath Accessible Apartment -

Port 19

Vacation condo Eagle View Cottage on Lake Pepin

The Cottage

Beach Lake Retreat with Private Lake and Hot Tub

New! Beach Lake: 4 Season Getaway!

Vacation rentals for every style

Popular amenities for Osseo vacation rentals

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