Holiday Rentals in Winona

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Our top choices for Winona holiday rentals

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (160)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is €123
includes taxes & fees
8 Jan - 9 Jan 2026
Cold Spring Plymouth Resort

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, (17)
"All excellent "
United States
Marc
The price is €393
includes taxes & fees
16 Dec - 17 Dec
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4)
"Great location & comfortable! "
United States
Jeanine L.
The price is €163
includes taxes & fees
12 Dec - 13 Dec
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath

Year-Round Outdoor Adventure Awaits at Lake Winnipesaukee

Year-Round Outdoor Adventure Awaits at Lake Winnipesaukee
Weirs Beach
10.0 out of 10, Exceptional, (1)
"Was a spacious 3 bedroom, clean and convenient to the beach area."
United States
David C.
The price is €188
includes taxes & fees
14 Dec - 15 Dec
Year-Round Outdoor Adventure Awaits at Lake Winnipesaukee

Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.6 out of 10, Exceptional, (15)
"Enjoyed our stay. "
United States
Ilene T.
The price is €148
includes taxes & fees
5 Jan - 6 Jan 2026
Cute Cedar Lodge Studio with Balcony & Lake Views!

Tenney Mountain Retreat, Plymouth & Rumney, NH

Tenney Mountain Retreat, Plymouth & Rumney, NH
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (2)
"Great hosts - very responsive and accommodating. We had a wonderful stay!"
United States
Alison H.
The price is €220
includes taxes & fees
15 Dec - 16 Dec
Tenney Mountain Retreat, Plymouth & Rumney, NH

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (72)
"Absolutely loved this house and would highly recommend! Communication was amazing with regards to questions or requests. Would stay here again!"
United States
Courtney F.
The price is €553
includes taxes & fees
12 Dec - 13 Dec
Idyllic Mountain and Lake Getaway

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (2)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
United States
kim M.
The price is €348
includes taxes & fees
22 Dec - 23 Dec
Cozy Cottage on a Lake, near Gunstock Mountain

Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (36)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is €261
includes taxes & fees
13 Dec - 14 Dec
Gorgeous Waterfront Condo with Lake Access & Views

The Gnome Home Cottage located near white mountain NH

The Gnome Home Cottage located near white mountain NH
Campton
9.4 out of 10, Exceptional, (55)
"This was a great place and convenient to highway. "
United States
Randy N.
The price is €256
includes taxes & fees
12 Dec - 13 Dec
The Gnome Home Cottage located near white mountain NH

White Mountain Cozy Cottage with Touch of Modern

White Mountain Cozy Cottage with Touch of Modern
Campton
9.6 out of 10, Exceptional, (47)
"The place is well situated off the main road. Great for a young family..."
United States
Andrew
The price is €256
includes taxes & fees
12 Dec - 13 Dec
White Mountain Cozy Cottage with Touch of Modern

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location
Gilford
10.0 out of 10, Exceptional, (2)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
The price is €477
includes taxes & fees
6 Jan - 7 Jan 2026
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Hiking Location

Lake Winnipesaukee Condo - Great for all seasons!

Lake Winnipesaukee Condo - Great for all seasons!
2.0 star property
Gilford
The price is €238
includes taxes & fees
12 Dec - 13 Dec
Lake Winnipesaukee Condo - Great for all seasons!

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)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is €244
includes taxes & fees
10 Jan - 11 Jan 2026
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Cozy condo with WiFi, fitness room in enjoyable Laconia

Cozy condo with WiFi, fitness room in enjoyable Laconia
Weirs Beach
10.0 out of 10, Exceptional, (5)
"Beautiful condo spacious and clean beautiful views loved the pool and hot tub! "
United States
Melissa D.
The price is €250
includes taxes & fees
15 Dec - 16 Dec
Cozy condo with WiFi, fitness room in enjoyable Laconia

The Lake View Nook - Lake Winnipesaukee

The Lake View Nook - Lake Winnipesaukee
Weirs Beach
The price is €165
includes taxes & fees
6 Jan - 7 Jan 2026
The Lake View Nook - Lake Winnipesaukee

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Sanbornton
10.0 out of 10, Exceptional, (13)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
The price is €613
includes taxes & fees
12 Dec - 13 Dec
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Mountain Cabin with long range views, privacy, and more.

Mountain Cabin with long range views, privacy, and more.
Campton
10.0 out of 10, Exceptional, (6)
"Great cabin, great location with an awesome view of the mountains "
United States
Kevin D.
The price is €260
includes taxes & fees
15 Dec - 16 Dec
Mountain Cabin with long range views, privacy, and more.

Warm and Cozy Condo: Perfect for Fall Foliage Getaways!

Warm and Cozy Condo: Perfect for Fall Foliage Getaways!
Weirs Beach
9.2 out of 10, Wonderful, (17)
"Perfect location for Weirs beach, the boardwalk and concert venue. "
United States
Kathleen A.
The price is €269
includes taxes & fees
14 Dec - 15 Dec
Warm and Cozy Condo: Perfect for Fall Foliage Getaways!

Modern Waterfront Condo with Views and Lake Access

Modern Waterfront Condo with Views and Lake Access
Tilton
9.4 out of 10, Exceptional, (9)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is €305
includes taxes & fees
16 Dec - 17 Dec
Modern Waterfront Condo with Views and Lake Access
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, apart-hotels, 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 favorite 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 depends 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 €123 per night. Entering your travel dates in the search wizard you might find 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, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with an outdoor tennis court and 1 hot tub.

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 Waukewan and Barnz's Meredith Cinema.

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.