Winona Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winona holiday rentals

9.6 out of 10, Exceptional, (11 reviews)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is NZ$307
includes taxes & fees
10 Mar - 11 Mar
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
9.6 out of 10, Exceptional, (60 reviews)
"Cute place! We enjoyed it! "
United States
Aubrey W.
The price is NZ$491
includes taxes & fees
10 Mar - 11 Mar
The Gnome Home Cottage located near white mountain NH
10.0 out of 10, Exceptional, (17 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is NZ$312
includes taxes & fees
10 Mar - 11 Mar
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Holiday Home in Ashland

Cold Spring Plymouth Resort
3.5 star property
9.2 out of 10, Wonderful, (195 reviews)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
The price is NZ$239
includes taxes & fees
23 Mar - 24 Mar
Cold Spring Plymouth Resort
9.8 out of 10, Exceptional, (38 reviews)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is NZ$528
includes taxes & fees
17 Mar - 18 Mar
Gorgeous Waterfront Condo with Lake Access & Views
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 NZ$450
includes taxes & fees
10 Mar - 11 Mar
Inviting condo in quiet locale with partial lake views, balcony & grilling area
10.0 out of 10, Exceptional, (18 reviews)
"Booked a summer getaway for my husband, my dog, and me. We had a great time - the house was comfortable and clean, and the location was excellent! "
United States
Laura B.
The price is NZ$903
includes taxes & fees
10 Mar - 11 Mar
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
9.6 out of 10, Exceptional, (34 reviews)
"Nice quiet visit. Lovely to be so close to the lake!"
United States
Phyllis S.
The price is NZ$569
includes taxes & fees
10 Mar - 11 Mar
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
9.6 out of 10, Exceptional, (55 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
The price is NZ$465
includes taxes & fees
14 Mar - 15 Mar
2 Bdrm Condo walking distance to Weirs Beach and much more!!
9.4 out of 10, Exceptional, (52 reviews)
"Super fun small cabin ,Modern bathroom new outside deck , easy walk to the river."
United States
matthew k.
The price is NZ$491
includes taxes & fees
10 Mar - 11 Mar
White Mountain Cozy Cottage with Touch of Modern
10.0 out of 10, Exceptional, (1 review)
"Great spot, especially for skiing at Gunstock. Very clean and comfortable. Host was available and responsive. Will definitely be coming back!"
United States
David H.
The price is NZ$1,056
includes taxes & fees
17 Mar - 18 Mar
[NEW] Cozy Cabin near Gunstock & Lake Winni
8.0 out of 10, Very good, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is NZ$575
includes taxes & fees
10 Mar - 11 Mar
Cozy three bedroom house located just five minutes from Lake Winnipesaukee
8.6 out of 10, Excellent, (8 reviews)
"Wonderful experience"
United States
Amarilis R.
The price is NZ$863
includes taxes & fees
11 Mar - 12 Mar
Cozy Cabin Waterville Estates
9.6 out of 10, Exceptional, (11 reviews)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is NZ$570
includes taxes & fees
11 Mar - 12 Mar
Modern Waterfront Condo with Views and Lake Access
9.6 out of 10, Exceptional, (38 reviews)
"Nice large, comfortable spaces to gather. Nicely equipped kitchen."
United States
Donna H.
The price is NZ$582
includes taxes & fees
10 Mar - 11 Mar
Come in & cozy up in beautiful lodge in Waterville Valley.
The price is NZ$364
includes taxes & fees
6 Apr - 7 Apr
Stunning Lake Views close to Weirs Beach & Gunstock

Holiday Home in Gilford

large-group mountain/lake getaway
9.6 out of 10, Exceptional, (18 reviews)
"We were very pleased with accommodations. We are 4 adults and the house had everything we needed for our visit. The beds were comfortable and the house was very clean. All communication with the host was answered quickly."
United States
Ruth R.
The price is NZ$992
includes taxes & fees
10 Mar - 11 Mar
large-group mountain/lake getaway

Holiday Home in Gilford

Idyllic Mountain and Lake Getaway
10.0 out of 10, Exceptional, (73 reviews)
"Amazing spot!"
United States
David E.
The price is NZ$1,043
includes taxes & fees
10 Mar - 11 Mar
Idyllic Mountain and Lake Getaway
9.6 out of 10, Exceptional, (15 reviews)
"Enjoyed our stay. "
United States
Ilene T.
The price is NZ$321
includes taxes & fees
6 Apr - 7 Apr
Cute Cedar Lodge Studio with Balcony & Lake Views!
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$239 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, 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 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.