Default HTG hotel image

Winona Vacation 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 vacation rentals

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (297 reviews)
"One of the best resort"
United States
Mehsan
The price is CA $187
CA $203 total
includes taxes & fees
Nov 12 - Nov 13
Cold Spring Plymouth Resort

2. Cedar Lodge Room-Private Balcony Close to Weirs!

Cedar Lodge Room-Private Balcony Close to Weirs!
Weirs Beach
9.6 out of 10, Exceptional, (5 reviews)
"Very clean, quiet and good location to points of interest. Nice beds!!"
United States
Deborah J.
The price is CA $154
CA $310 total
includes taxes & fees
Nov 8 - Nov 9
Cedar Lodge Room-Private Balcony Close to Weirs!

3. Weirs beach retreat

Weirs beach retreat
Weirs Beach
9.8 out of 10, Exceptional, (8 reviews)
"Just a minutes drive to the waterfront and shops. Great location "
United States
Wayne W.
The price is CA $147
CA $380 total
includes taxes & fees
Nov 8 - Nov 9
Weirs beach retreat

4. Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi

Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi
Weirs Beach
9.6 out of 10, Exceptional, (5 reviews)
"Condo was very clean, rooms her good sized, each having a separate bathroom was ideal. Also centrally located for attending Laconia bike week. About 4 miles from Weirs beach, walking distance to Cumberland Farms. The host, Margaret, was exceptional. Would highly recommend."
United States
Darren
The price is CA $127
CA $449 total
includes taxes & fees
Nov 10 - Nov 11
Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi

5. Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach

Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach
Weirs Beach
10.0 out of 10, Exceptional, (3 reviews)
"Good location with clean and comfortable beds. Thx!"
United States
Phil C.
The price is CA $140
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
Ground-Floor Lakes Region Getaway | Patio Near Weirs Beach

6. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is CA $154
CA $310 total
includes taxes & fees
Nov 8 - Nov 9
Cedar Lodge Room 2 Queen Beds & Private Balcony

7. 1 Bedroom Lake Winnipesaukee Condo

1 Bedroom Lake Winnipesaukee Condo
Gilford
9.6 out of 10, Exceptional, (32 reviews)
"Great experience"
United States
Radu
The price is CA $168
CA $380 total
includes taxes & fees
Nov 8 - Nov 9
1 Bedroom Lake Winnipesaukee Condo

8. 2 Bedroom Cedar Lodge Condo w/ Loft & private balcony

2 Bedroom Cedar Lodge Condo w/ Loft & private balcony
Weirs Beach
The price is CA $173
CA $383 total
includes taxes & fees
Dec 8 - Dec 9
2 Bedroom Cedar Lodge Condo w/ Loft & private balcony

9. Inviting 1BR Lakeview 2nd-Floor - Balcony

Inviting 1BR Lakeview 2nd-Floor - Balcony
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 CA $108
CA $378 total
includes taxes & fees
Nov 8 - Nov 9
Inviting 1BR Lakeview 2nd-Floor - Balcony

10. 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, (176 reviews)
"We loved our stay. Very clean and in a great location in Meredith."
United States
Rebecca R.
The price is CA $209
CA $433 total
includes taxes & fees
Nov 8 - Nov 9
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

11. Cedar Lodge Condo w/ Loft and private balcony

Cedar Lodge Condo w/ Loft and private balcony
Weirs Beach
10.0 out of 10, Exceptional, (1 review)
"Had an incredible stay for a Father/Son overnight trip to Laconia. The property was clean, incredibly safe, quiet and relaxing, the amenities were very nice and perfect for a vacation of any length. Perfect for family trips, couples getaways, solo adventures and friend getaways. This property is close to anything you want to do in that area. Has a nice pool, basketball, firepit, BBQ spots, places to relax and enjoy your drink or coffee to watch the sunset over the lake or sit under the starry...
United States
Steven F.
The price is CA $154
CA $310 total
includes taxes & fees
Nov 8 - Nov 9
Cedar Lodge Condo w/ Loft and private balcony

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

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
10.0 out of 10, Exceptional, (53 reviews)
"The apartment was very comfortable and just as pictured. We had a wonderful stay! It’s a great location for walking in Meredith and an easy drive to ski at Gunstock. "
United States
Karen O.
The price is CA $188
CA $408 total
includes taxes & fees
Nov 10 - Nov 11
Meredith Bay - Brand New 1st Floor Apartment In Private Home

13. Lakeside Cabin 1 with Kitchenette, Not Dog Friendly

Lakeside Cabin 1 with Kitchenette, Not Dog Friendly
Holderness
The price is CA $202
CA $449 total
includes taxes & fees
Nov 9 - Nov 10
Lakeside Cabin 1 with Kitchenette, Not Dog Friendly

14. Lake Views Close to Weirs in Cedar Lodge Complex

Lake Views Close to Weirs in Cedar Lodge Complex
Weirs Beach
The price is CA $154
CA $310 total
includes taxes & fees
Nov 8 - Nov 9
Lake Views Close to Weirs in Cedar Lodge Complex

15. Lakes Region Escape | Private Balcony Near Weirs Beach

Lakes Region Escape | Private Balcony Near Weirs Beach
Weirs Beach
10.0 out of 10, Exceptional, (1 review)
"Great location. Close to the strip"
United States
Adam C.
The price is CA $140
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
Lakes Region Escape | Private Balcony Near Weirs Beach

16. Cozy Studio w/king bed, close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

Cozy Studio w/king bed, close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
Laconia
10.0 out of 10, Exceptional, (34 reviews)
"Easy process and great location"
United States
Daniel
The price is CA $191
CA $436 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Studio w/king bed, close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

17. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (7 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
Gilford Perfect Getaway Pool, WIFI & Free Parking

18. 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, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is CA $202
CA $379 total
includes taxes & fees
Nov 16 - Nov 17
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

19. 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, (71 reviews)
"Stay was great ! Little small for multiple people but great place for a couple getaway weekend"
United States
Jesse C.
The price is CA $226
CA $420 total
includes taxes & fees
Nov 8 - Nov 9
The Gnome Home Cottage located near white mountain NH

20. Lakeside Cabin 6 with Kitchen

Lakeside Cabin 6 with Kitchen
Holderness
10.0 out of 10, Exceptional, (2 reviews)
"The two bedroom cottage I stayed in at Cottage Place during a relocation was really nice. It was very quiet, comfortable, and had everything you could want for a relaxing and memorable stay. The staff was very nice and helpful, and the location right next to Squam Lake was terrific. I look forward to staying there again in the Fall."
United States
david
The price is CA $281
CA $541 total
includes taxes & fees
Nov 10 - Nov 11
Lakeside Cabin 6 with Kitchen
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winona Hotel Reviews

Find out more about Winona

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This vacation home rental outside of Winona is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games 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 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.