Winona Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

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, (177 reviews)
"The apartment was great, we enjoyed the pool, jacuzzi and sauna, and the staff were super nice!!"
United States
Jenn
The price is ￥20,975
￥22,758 total
includes taxes & fees
Feb 22 - Feb 23
Cold Spring Plymouth Resort
Beach

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, (57 reviews)
"Cute place! We enjoyed it! "
United States
Aubrey W.
The price is ￥24,103
￥45,924 total
includes taxes & fees
Feb 1 - Feb 2
The Gnome Home Cottage located near white mountain NH
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, (11 reviews)
"Great property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is ￥22,668
￥28,035 total
includes taxes & fees
Jan 25 - Jan 26
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, (17 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 ￥27,963
￥73,682 total
includes taxes & fees
Feb 2 - Feb 3
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
TV, table tennis

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 reviews)
"Enjoyed our stay. "
United States
Ilene T.
The price is ￥9,820
￥26,033 total
includes taxes & fees
Feb 10 - Feb 11
Cute Cedar Lodge Studio with Balcony & Lake Views!
Property grounds

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 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is ￥22,668
￥28,035 total
includes taxes & fees
Jan 25 - Jan 26
Cottage 7 - Year Round - Pet Friendly - Stand Alone 1 Bedroom / 1 Bath
Smart TV, fireplace, DVD player, books

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 reviews)
"Great cabin, great location with an awesome view of the mountains "
United States
Kevin D.
The price is ￥15,693
￥47,987 total
includes taxes & fees
Feb 8 - Feb 9
Mountain Cabin with long range views, privacy, and more.
Terrace/patio

Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (36 reviews)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is ￥16,242
￥46,518 total
includes taxes & fees
Jan 25 - Jan 26
Gorgeous Waterfront Condo with Lake Access & Views
Pool

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 ￥11,096
￥41,934 total
includes taxes & fees
Feb 1 - Feb 2
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Exterior

Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
9.8 out of 10, Exceptional, (45 reviews)
"Very clean and very comfortable. Short walk to downtown made our stay perfect. "
United States
Julian G.
The price is ￥21,258
￥45,253 total
includes taxes & fees
Jan 25 - Jan 26
Meredith Bay - Brand New 1st Floor Apartment In Private Home
Beach nearby

Cozy Winter Escape

Cozy Winter Escape
Weirs Beach
9.2 out of 10, Wonderful, (17 reviews)
"Perfect location for Weirs beach, the boardwalk and concert venue. "
United States
Kathleen A.
The price is ￥15,693
￥48,331 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Winter Escape
Private kitchen

Cozy Cottage on a Lake, near Gunstock Mountain

Cozy Cottage on a Lake, near Gunstock Mountain
Gilmanton
9.0 out of 10, Wonderful, (2 reviews)
"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 ￥27,107
￥62,779 total
includes taxes & fees
Jan 25 - Jan 26
Cozy Cottage on a Lake, near Gunstock Mountain
Beach

Taigh Loch - Lakes Region Retreat!

Taigh Loch - Lakes Region Retreat!
Alton
9.8 out of 10, Exceptional, (14 reviews)
"Great place! Owners were very responsive with any questions we had. Per friendly was a plus. We would definitely stay here again."
United States
Shawn M.
The price is ￥23,778
￥57,446 total
includes taxes & fees
Jan 25 - Jan 26
Taigh Loch - Lakes Region Retreat!
Private kitchen

Tenney Mountain Retreat, Plymouth & Rumney, NH

Tenney Mountain Retreat, Plymouth & Rumney, NH
Plymouth
8.8 out of 10, Excellent, (3 reviews)
"Amazing place to stay. Great communication with host. Will plan on staying again. "
United States
Erin V.
The price is ￥18,230
￥47,299 total
includes taxes & fees
Jan 27 - Jan 28
Tenney Mountain Retreat, Plymouth & Rumney, NH
Beach nearby

Lake Access, Poolside Deck & Ski Nearby

Lake Access, Poolside Deck & Ski Nearby
Gilford
8.0 out of 10, Very Good, (12 reviews)
"Clean, comfortable and perfect location for our needs. Host is very responsive and easy to work with."
United States
Dan K.
The price is ￥11,889
￥28,402 total
includes taxes & fees
Jan 26 - Jan 27
Lake Access, Poolside Deck & Ski Nearby
Dining

Campton Log Cabin- Close to it all!

Campton Log Cabin- Close to it all!
Campton
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay!! The cabin was spotless and in a great location. Jenna was great to deal with and she always answered any questions I had about the cabin. I would definitely recommend staying there."
United States
Kevin W.
Campton Log Cabin- Close to it all!
View from property

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Meredith
10.0 out of 10, Exceptional, (170 reviews)
"We loved our stay, the apartment was in the heart of town, very clean and comfortable! The hosts were very responsive and accommodating. "
United States
Erin S.
The price is ￥23,619
￥48,159 total
includes taxes & fees
Jan 25 - Jan 26
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Beach

White Mountain Cozy Cottage with Touch of Modern

White Mountain Cozy Cottage with Touch of Modern
Campton
9.6 out of 10, Exceptional, (50 reviews)
"Super fun small cabin ,Modern bathroom new outside deck , easy walk to the river."
United States
matthew k.
The price is ￥24,111
￥46,112 total
includes taxes & fees
Jan 25 - Jan 26
White Mountain Cozy Cottage with Touch of Modern
Beach nearby

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Cozy Cabin near Tuftonboro & Lake Winnipesaukee
Tuftonboro
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property "
United States
Keith B.
The price is ￥24,412
￥68,798 total
includes taxes & fees
Jan 26 - Jan 27
Cozy Cabin near Tuftonboro & Lake Winnipesaukee
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
9.6 out of 10, Exceptional, (22 reviews)
"Great location for seeing concerts."
United States
Kevin Y.
The price is ￥16,407
￥39,129 total
includes taxes & fees
Feb 2 - Feb 3
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
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

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

10/10 Excellent
"The front desk workers with extremely friendly and helpful. Hotel was clean. Breakfast was clean and good. "
Jacqueline 1-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Find out more about Winona

Search for holiday rentals in Winona on Expedia! You can easily find your home rentals, villas, holiday apartments in Winona using one of the methods below:

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Look no further and take a look at our great range of rental properties in Winona!

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, a fireplace, 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. You can relax into your vacation with an outdoor tennis court and a hot tub.

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 Waukewan and Barnz's Meredith Cinema.

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.