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Winona Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Winona vacation rentals

Deluxe Apartment, 2 Bedrooms, Kitchen | Mountain view

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (226 reviews)
"nice place to stay while xc ski"
United States
Julia
$193 nightly
The price is $209
Jul 20 - Jul 21
Total with taxes and fees
Cold Spring Plymouth Resort
House (2 Bedrooms) | Interior

Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (1 review)
"We’ll kept "
United States
Denise
$426 nightly
The price is $462
Jul 23 - Jul 24
Total with taxes and fees
Cozy Tuftonboro Escape: Steps to Private Beaches!
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time during our stay. The cottage was in a great location, exactly as advertised, and spotlessly clean. The hot tub was great. Can’t think of a single thing we’d change. Would love to come back again during the summer months."
United States
Dawn P.
$363 nightly
The price is $394
Jul 8 - Jul 9
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
Terrace/patio

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (12 reviews)
"Great place "
United States
Anonymous traveler
$267 nightly
The price is $289
Jul 8 - Jul 9
Total with taxes and fees
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Outdoor dining

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (18 reviews)
"We had a wonderful stay at Grandma’s with our two little boys and dog. It was clean, cozy and a perfect location for our weekend ice fishing trip! We enjoyed walking the rail trail, watching ducks by the dock, passing snowmobiles, and playing puzzles/games. Highly recommend for a family getaway. We would definitely stay again."
United States
Nicole C.
$553 nightly
The price is $600
Jul 8 - Jul 9
Total with taxes and fees
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Beach

White Mountain Cozy Cottage with Touch of Modern

White Mountain Cozy Cottage with Touch of Modern
Campton
9.4 out of 10, Exceptional, (53 reviews)
"The cottage was perfect for our long weekend getaway. It was more spacious than expected and convenient location. The host is very responsive and accommodating. Would stay again!"
United States
Emily F.
$277 nightly
The price is $301
Jul 8 - Jul 9
Total with taxes and fees
White Mountain Cozy Cottage with Touch of Modern
Classic Apartment, Non Smoking | Private kitchen | Full-size fridge, microwave, oven, stovetop

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
$514 nightly
The price is $558
Jul 23 - Jul 24
Total with taxes and fees
9 Lake Street
Terrace/patio

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
$317 nightly
The price is $344
Jul 8 - Jul 9
Total with taxes and fees
Cottage 8-9 - Year Round - Pet Friendly - Stand Alone 2 Bedroom / 2 Bath
Interior

Beautiful 1 bedroom condo-Lake views. Now offering monthly rental.

Beautiful 1 bedroom condo-Lake views. Now offering monthly rental.
Laconia
9.6 out of 10, Exceptional, (28 reviews)
"Very friendly host and a nice place!"
United States
Brian P.
$300 nightly
The price is $325
Jul 8 - Jul 9
Total with taxes and fees
Beautiful 1 bedroom condo-Lake views. Now offering monthly rental.
Beach

Taigh Loch - Lakes Region Retreat!

Taigh Loch - Lakes Region Retreat!
Alton
9.8 out of 10, Exceptional, (16 reviews)
"Lovely place and stay. We got stuck at the bottom of the driveway after the snow, but with the hosts' help getting the drive plowed and a little elbow grease we got out just fine. We'll have a 4WD by the next time we're up there!"
United States
John R.
Taigh Loch - Lakes Region Retreat!
Exterior

Modern Waterfront Condo with Views and Lake Access

Modern Waterfront Condo with Views and Lake Access
Tilton
9.6 out of 10, Exceptional, (12 reviews)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
$405 nightly
The price is $440
Jul 9 - Jul 10
Total with taxes and fees
Modern Waterfront Condo with Views and Lake Access
House (1 Bedroom) | Interior

6 Mi to Polar Caves! All-season Getaway w/ Sauna

6 Mi to Polar Caves! All-season Getaway w/ Sauna
3.0 star property
Plymouth
$334 nightly
The price is $363
Jul 13 - Jul 14
Total with taxes and fees
6 Mi to Polar Caves! All-season Getaway w/ Sauna
Sun loungers, beach towels

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (27 reviews)
"Perfect property for us right across from the lake Very well decorated and clean The owner was very attentive and answered every question I had! Will definitely be staying there again"
United States
Richard
$504 nightly
The price is $547
Jul 17 - Jul 18
Total with taxes and fees
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Interior

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Gilmanton
9.8 out of 10, Exceptional, (36 reviews)
"Lovely stay in a quiet area. The hot tub was great to unwind in after hiking in the area!"
United States
Cristofer V.
$553 nightly
The price is $600
Jul 9 - Jul 10
Total with taxes and fees
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Living area

Cabin in the Woods

Cabin in the Woods
Franklin
9.6 out of 10, Exceptional, (8 reviews)
"Great cozy cabin! Terrific fire pit and nice wood grain"
United States
Tyler P.
$218 nightly
The price is $237
Jul 8 - Jul 9
Total with taxes and fees
Cabin in the Woods
Beach nearby

Private Pond Cabin with Lake Access & Fire Pit

Private Pond Cabin with Lake Access & Fire Pit
Tuftonboro
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property "
United States
Keith B.
$569 nightly
The price is $617
Jul 13 - Jul 14
Total with taxes and fees
Private Pond Cabin with Lake Access & Fire Pit
Dining

Cozy, Pet-Friendly Escape Near Lake & Mountains

Cozy, Pet-Friendly Escape Near Lake & Mountains
Gilford
10.0 out of 10, Exceptional, (43 reviews)
"Really cozy and clean home. Hosts were wonderful too. "
United States
jacqueline S.
$548 nightly
The price is $595
Jul 16 - Jul 17
Total with taxes and fees
Cozy, Pet-Friendly Escape Near Lake & Mountains
Property grounds

Cozy hotel-style suite right on the water, shared patio, free WiFi

Cozy hotel-style suite right on the water, shared patio, free WiFi
Alton
9.0 out of 10, Wonderful, (19 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
$290 nightly
The price is $315
Jul 8 - Jul 9
Total with taxes and fees
Cozy hotel-style suite right on the water, shared patio, free WiFi
Outdoor dining

Attractive studio in waterfront location w/free WiFi, water views, kitchenette

Attractive studio in waterfront location w/free WiFi, water views, kitchenette
Alton
8.2 out of 10, Very Good, (11 reviews)
"Loved everything, especially the price for such a perfect stay."
United States
John B.
$290 nightly
The price is $315
Jul 8 - Jul 9
Total with taxes and fees
Attractive studio in waterfront location w/free WiFi, water views, kitchenette
Exterior

Bear Cub Cabin- Waterfront Cabin

Bear Cub Cabin- Waterfront Cabin
Holderness
10.0 out of 10, Exceptional, (1 review)
"A Perfect cabin. It was very beautiful location im sad it was only for one night. We'll definitely booke here again! We loved it!"
United States
Bruce D.
$514 nightly
The price is $553
Jul 10 - Jul 11
Total with taxes and fees
Bear Cub Cabin- Waterfront Cabin
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.
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Top Winona Hotel Reviews

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

10/10 Excellent
"Mill Falls is a great hotel with the lake, pools, and restaurants right where you stay….no need to leave so much to do there!!! Cannot beat the Lake View!!!!"
diane 1-night trip
Posted 5 hours ago
Mill Falls Resort Collection at the Lake

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $209 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we have vacation rentals close to top sights in Winona, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Winona has to offer?

Cold Spring Plymouth Resort: This vacation home rental outside of Winona is located in the mountains and has an outdoor pool, an outdoor tennis court, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. Make the most of the hot tub in this rental home to help you unwind.

How many vacation rentals are there in Winona?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Winona stay.

What’s there to see and do in Winona?

Explore the area and family-friendly sights such as Squam Lakes Natural Science Center, or get out into nature at a spot like Winona Lake. In the larger area, you’ll find Lake Winnipesaukee and Lake Waukewan.

What’s a vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.