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Winona Holiday Rentals

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Our top choices for Winona holiday rentals

Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views

Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views
Alton
7.6 out of 10, Good, (14 reviews)
"Awesome location, nice swimming area with dock. 3 grills so there is no wait time. On property caretaker answered any questions. "
United States
Jeffrey D.
The price is AU$443
includes taxes & fees
10 June - 11 June
Wonderful studio steps from the bay w/free WiFi, kitchenette, great water views

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (220 reviews)
"Townhouses on the golf course are amazing. Beautiful and spacious inside with stunning views."
United States
Stephanie
The price is AU$214
includes taxes & fees
10 June - 11 June
Cold Spring Plymouth Resort

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (18 reviews)
"Nice location on the lake."
United States
Mary L.
The price is AU$478
includes taxes & fees
28 June - 29 June
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is AU$384
includes taxes & fees
10 June - 11 June
Cedar Lodge Room 2 Queen Beds & Private Balcony

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
The price is AU$509
includes taxes & fees
10 June - 11 June
6 Mi to Polar Caves! All-season Getaway w/ Sauna

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, (11 reviews)
"Great place "
United States
Anonymous traveller
The price is AU$248
includes taxes & fees
10 June - 11 June
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (19 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is AU$268
includes taxes & fees
10 June - 11 June
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cabin in the Woods

Cabin in the Woods
Franklin
9.8 out of 10, Exceptional, (6 reviews)
"Great cozy cabin! Terrific fire pit and nice wood grain"
United States
Tyler P.
The price is AU$337
includes taxes & fees
16 June - 17 June
Cabin in the Woods

Best value on Newfound Lake NH 2 day min

Best value on Newfound Lake NH 2 day min
Bristol
8.8 out of 10, Excellent, (26 reviews)
"Perfect stay! Exactly as described, great little cabin and was perfect for a family weekend "
United States
Kasey C.
The price is AU$718
includes taxes & fees
10 June - 11 June
Best value on Newfound Lake NH 2 day min

The Gnome Home Cottage located near white mountain NH

The Gnome Home Cottage located near white mountain NH
Campton
9.6 out of 10, Exceptional, (62 reviews)
"Place was perfect. Located very close to a nice restaurant with live music. "
United States
Kevin O.
The price is AU$423
includes taxes & fees
16 June - 17 June
The Gnome Home Cottage located near white mountain NH

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
8.8 out of 10, Excellent, (17 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
The price is AU$440
includes taxes & fees
28 June - 29 June
Cozy hotel-style suite right on the water, shared patio, free WiFi

Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
Center Tuftonboro
10.0 out of 10, Exceptional, (13 reviews)
"It was very cozy a 10/10 I would definitely pick this house again it was a good house to stay at I don’t regret booking!"
United States
Bartolome V.
The price is AU$658
includes taxes & fees
10 June - 11 June
Cozy Tuftonboro Escape: Steps to Private Beaches!

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is AU$396
includes taxes & fees
10 June - 11 June
Inviting condo in quiet locale with partial lake views, balcony & grilling area

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.
The price is AU$868
includes taxes & fees
10 June - 11 June
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

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
The price is AU$651
includes taxes & fees
10 June - 11 June
Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Cozy Cabin near Tuftonboro & Lake Winnipesaukee
Tuftonboro
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful property "
United States
Keith B.
The price is AU$712
includes taxes & fees
16 June - 17 June
Cozy Cabin near Tuftonboro & Lake Winnipesaukee

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, (27 reviews)
"Very friendly host and a nice place!"
United States
Brian P.
The price is AU$650
includes taxes & fees
5 July - 6 July
Beautiful 1 bedroom condo-Lake views. Now offering monthly rental.

Luxury 4BR Waterville Retreat w/ Arcade

Luxury 4BR Waterville Retreat w/ Arcade
Campton
8.4 out of 10, Very good, (6 reviews)
"Gorgeous views and plenty of space to spread out. Already booked the second trip"
United States
john c.
The price is AU$991
includes taxes & fees
10 June - 11 June
Luxury 4BR Waterville Retreat w/ Arcade

Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni

Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni
Gilford
10.0 out of 10, Exceptional, (1 review)
"Very clean and well appointed property. Kitchen well stocked and bathrooms very nice to use. Very pleasant to just stay in and enjoy the property. We could have stayed longer. Communication was easy and quick feedback. Owners provided useful information on the area on things to do and places to go. Would definitely stay there again if in that area."
United States
Todd B.
The price is AU$1,005
includes taxes & fees
24 June - 25 June
Gunstock Chalet - Close to Gunstock, BNH Pavilion Concerts, and Lake Winni

Cedar Lodge Condo w/ Loft and private balcony

Cedar Lodge Condo w/ Loft and private balcony
Weirs Beach
The price is AU$384
includes taxes & fees
10 June - 11 June
Cedar Lodge Condo w/ Loft and private balcony
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

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$214 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday 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 holiday.

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 holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay.

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

Cold Spring Plymouth Resort: This holiday home rental outside of Winona is located in the mountains, and has an outdoor pool, an outdoor tennis court and a BBQ 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 Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Winona?

With 3 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Lake Winnipesaukee and Lake Waukewan.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.