Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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

Guest favorite

Cottage in Henderson

4.83 out of 5 average rating, 24 reviews

Amazing Lake View 3-Bedroom Cottage close to ramp

Relax with the whole family at this peaceful Cottage lake-view, home. If you’re boating or fishing, it’s just a short distance (1/4 mile) to the boat ramp. If you’re looking to put your toes in the water, let the kids swim and start your adventures, it’s just a short walk to the water or hop on our golf cart for a super quick trip to dip! Chances are, you’ll be spending a great amount of time, simply admiring the most gorgeous lake view and lounging on the very spacious, back deck. Come Relax!!!

Guest favorite

Cabin in Black River Township

4.98 out of 5 average rating, 66 reviews

Well-Designed Cozy Cabin near lake and hiking

Designed for families as a relaxing spot to get away from the hustle & bustle of life, the "Hillside Hideaway" is a 2 bedroom, 1 bath cabin perched on a hill in southeastern Missouri with a gorgeous sunset view from the screen porch. We have a well-stocked kitchen, laundry, fire pit, and plenty of toys and games for the whole family. It is just a couple of miles to a sandy swimming beach at Lake Wappapello, the boat ramp at Chaonia Landing, and many hiking trails in Lake Wappapello State Park.

Guest favorite

Treehouse in Greenville

5 out of 5 average rating, 232 reviews

Secluded couple's treehouse "The Roost" + hot tub

"The Roost" is rustic but not primitive treehouse 2 hrs south of St Louis near Wappapello Lake. Yes it has indoor plumbing & running water. Accommodates two adults, has a fully equipped kitchen and breakfast items are provided for you to cook. Surrounded by thousands of acres of national forest. Observe wildlife sightings from the deck while soaking in the hot tub, sleep comfortably in a queen size pillowtop Serta bed on a Motion Air base, and relax as you enjoy the ambience of the fireplace.

Guest favorite

Cabin in Gassville

4.91 out of 5 average rating, 11 reviews

Cabin overlooking White River, Valley, Boston Mtns

Rainbow Ridge Retreat your cabin on the bluff overlooking the valley, Boston Mountains & the White River. Fantastic views, fire pit, outdoor/Indoor fireplaces, pool table & hot tub. Relaxation for the whole family & friends. No 3 top rated Trout fishing in the US. Numerous local guides available, 5 min to boat launch. Fishing, boating, tubing, floating, golf, kayaking, hiking etc near by. No Smoking. No Pets. No Parties. Only approved number of guests. Please don’t roll luggage on wood floors.

Guest favorite

Cabin in Van Buren

5 out of 5 average rating, 32 reviews

Private Hilltop Cabin Near Current River

Come enjoy a stay at Orchard Hilltop Getaway just walking distance from all the amenities and less than 1 mile from Current River. Our clean and cozy cabin comfortably sleeps 6 people and has everything you need for your next trip. Located in the heart of all Van Buren has to offer, this location makes a perfect base for your adventures. Spend the day on the river swimming or by rent/bring tubes, canoes, kayaks, or rafts. There are also various other places nearby to experience the Ozarks.

Guest favorite

Cabin in Licking

5 out of 5 average rating, 9 reviews

Montauk Nature Retreat - New Listing on Acreage!

If you're looking for a peaceful and relaxing cabin spot on acreage with beautiful views and close to Montauk state park or many other water activities then look no further. This 4 BR/2 BA 1,700 sq feet place has been newly renovated to include all of the necessary amenities while on vacation. A fully stocked and updated kitchen, two bathrooms (one shower, one tub/shower combo), a massive living room with comfortable couches looking towards a 65 inch smart tv. Just 3 miles from Montauk!!

Guest favorite

Villa in Lebanon

4.95 out of 5 average rating, 37 reviews

Villa at River Ranch

Villa @ River Ranch: A spacious finely-appointed luxury hideaway, nestled in the Ozark Mountains. Custom-built home sits at the top of a prominent hill at the center of a beautiful, privately-owned 500-acre river valley grazing ranch surrounded on all sides by the Ozark mountains. Enjoy this magnificent retreat, with panoramic views, well-designed indoor and outdoor living spaces, extensive lawns, mature trees, and the kind of beauty that refreshes the spirit. Minumum stay: 2 nights.

Guest favorite

Home in Midway

4.92 out of 5 average rating, 24 reviews

Large Home on Bull Shoals Lake w/Lake Access

Welcome! We hope that you have a wonderful experience and make many memorable memories at our private lake home . Relax, enjoy the view, watch boats, wildlife, and cook out. Take a walk to the lake, fish and enjoy all lake activities. The home includes 6 bedrooms/3 baths and sits on 3 acres which joins the core of engineers. We provide kayaks and storage for your boat. The boat launch is 0.5 mile from the home. Please reach out for any questions as this house provides many extras.

Guest favorite

Home in Flippin

4.94 out of 5 average rating, 127 reviews

Amazing Spring Rates On White River! Great Fishing

We welcome you to our home which sits on The White River! This is a 3 bedroom 2 bath home. There is a set of stairs in the house and down to the river. Amazing views from this home from almost every spot. It sits on 200’ of World Famous White River frontage! There is public boat ramp access 3/10 of a mile from the house. It is great kayaking and fishing in the back of the house. If you need a guide we highly recommend Cox's Guide Service @ #870-706-1648. We thank you so much!

Superhost

Condo in Hardy

4.63 out of 5 average rating, 64 reviews

Cozy Family Vacation Condo #5, Near Spring River

Not brand new, but the price is good and, it’s pretty dang nice! More than a room, enjoy a wonderful stay in this freshly remodeled suite provides two cozy bedrooms, a full kitchen, a dining and living room, and everything a full vacation condo offers. Wake up to freshly brewed Starbucks stocked in your coffee station. Shops and fun just steps away, an ultimate escape. Just a tip: The Corner Booth restaurant has amazing waffles! Book now for a stay you'll never forge

Guest favorite

Loft in Mountain Home

4.95 out of 5 average rating, 96 reviews

The Heights 1 - Downtown Loft in Mtn. Home, AR

Brand new, high-end downtown loft in Mountain Home, Arkansas! This 2-bedroom/1-bathroom high-end loft has luxurious spa-like finishes and is within walking distance to downtown Mountain Home. This apartment has 2 bedrooms, one with a queen bed and the other with twin over twin bunk beds. There is a full kitchen, full bath, and comfortable living room. Every room has a TV. There is also an outdoor eating area with a grill! Come see us!

Guest favorite

Home in Farmington

4.97 out of 5 average rating, 30 reviews

Come experience relaxation at Eva’s Retreat LLC.

Newly renovated home that is perfect for families or couples. A great place to relax and unwind after a day of enjoying all the local attractions that farmington has to offer. Such as beautiful wineries, local state parks, and just minutes away from 3 local golf courses. Close enough to everything with the feel of a country setting.