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Winona Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Winona vacation rentals

Deluxe Apartment, 2 Bedrooms, Kitchen | Mountain view

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (248 reviews)
"The room and resort was great! The staff was excellent and sweet! We will definitely be back!"
United States
Stacey
The price is AED 486
AED 527 total
includes taxes & fees
7 Sep - 8 Sep
Cold Spring Plymouth Resort
Outdoor spa tub

2. Walk to Downtown Meredith | Private Pool & Hot Tub

Walk to Downtown Meredith | Private Pool & Hot Tub
Meredith
9.8 out of 10, Exceptional, (64 reviews)
"Stayed for a ski weekend at Gunstock. It was my second time at this house & everything was fantastic."
United States
Jessica H.
The price is AED 3,056
AED 5,085 total
includes taxes & fees
23 Aug - 24 Aug
Walk to Downtown Meredith | Private Pool & Hot Tub
Exterior

3. 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, (51 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.
Meredith Bay - Brand New 1st Floor Apartment In Private Home
Terrace/patio

4. Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.

Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.
Holderness
10.0 out of 10, Exceptional, (2 reviews)
"Everything was wonderful!! "
United States
Scott O.
Escape to Central Escape’s 2-bedroom option, perfectly located in New Hampshire’s Lakes Region. Enjoy a private year-round hot tub, spacious backyard with yard games, and easy access to downtown Meredith, Squam Lake, and summer concerts.
Terrace/patio

5. Central Escape is a spacious Lakes Region retreat just 5 minutes from downtown Meredith, less than a mile to Squam Lake and 20 minutes to concerts at the Bank of New Hampshire Pavilion. Enjoy the private year-round hot tub, fire pit, yard games!

Central Escape is a spacious Lakes Region retreat just 5 minutes from downtown Meredith, less than a mile to Squam Lake and 20 minutes to concerts at the Bank of New Hampshire Pavilion. Enjoy the private year-round hot tub, fire pit, yard games!
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at Central Escape. It fit our needs perfectly. The hosts were very easy to communicate with and helpful. We would definitely stay here again."
United States
Laurie O.
The price is AED 1,690
AED 3,439 total
includes taxes & fees
9 Sep - 10 Sep
Central Escape is a spacious Lakes Region retreat just 5 minutes from downtown Meredith, less than a mile to Squam Lake and 20 minutes to concerts at the Bank of New Hampshire Pavilion. Enjoy the private year-round hot tub, fire pit, yard games!
Property grounds

6. Lakefront Retreat: Swim, Kayak, Fish, and more!

Lakefront Retreat: Swim, Kayak, Fish, and more!
Sanbornton
10.0 out of 10, Exceptional, (14 reviews)
"Great space to enjoy family & friends."
United States
Anonymous traveler
Lakefront Retreat: Swim, Kayak, Fish, and more!
Pool

7. 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 AED 257
AED 984 total
includes taxes & fees
8 Sep - 9 Sep
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Dining

8. Spacious Lakes Region Retreat—Game Room & Gazebo

Spacious Lakes Region Retreat—Game Room & Gazebo
Meredith
10.0 out of 10, Exceptional, (9 reviews)
"House was immaculate with all the amenities we needed. Beautiful home."
United States
Bernadette M.
Spacious Lakes Region Retreat—Game Room & Gazebo
Beach nearby

9. Squam Lake 3 bed 3 bath (Suite #7)

Squam Lake 3 bed 3 bath (Suite #7)
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"Great spot for a fun long weekend."
United States
katherine c.
The price is AED 1,531
AED 2,238 total
includes taxes & fees
8 Sep - 9 Sep
Squam Lake 3 bed 3 bath (Suite #7)
Beach nearby

10. Squam waterfront 2 bed 2 bath (Suite 8)

Squam waterfront 2 bed 2 bath (Suite 8)
Holderness
10.0 out of 10, Exceptional, (3 reviews)
"Right on the water! Great views, wonderful beach/dock, great little place to stay!"
United States
colette c.
The price is AED 1,168
AED 1,702 total
includes taxes & fees
8 Sep - 9 Sep
Squam waterfront 2 bed 2 bath (Suite 8)
Beach nearby

11. Bear Cub Cabin- Waterfront Cabin

Bear Cub Cabin- Waterfront Cabin
Holderness
10.0 out of 10, Exceptional, (1 review)
"A Perfect cabin. It was very beautiful location im sad it was only for one night. We'll definitely booke here again! We loved it!"
United States
Bruce D.
The price is AED 1,454
AED 2,058 total
includes taxes & fees
8 Sep - 9 Sep
Bear Cub Cabin- Waterfront Cabin
Exterior

12. Luxury Lakefront w/Hot Tub, Beach, Mountain Views!

Luxury Lakefront w/Hot Tub, Beach, Mountain Views!
Moultonborough
10.0 out of 10, Exceptional, (64 reviews)
"This was a great place to stay, loved it!!"
United States
Kenton M.
The price is AED 10,606
AED 12,993 total
includes taxes & fees
2 Sep - 3 Sep
Luxury Lakefront w/Hot Tub, Beach, Mountain Views!
Marina

13. Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!

Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
Weirs Beach
9.6 out of 10, Exceptional, (74 reviews)
"Great location, only 5 miles from our concert venue and off the main routes so it was quite quiet."
United States
VERNON
The price is AED 784
AED 1,545 total
includes taxes & fees
14 Sep - 15 Sep
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!
Smart TV, video games

14. Cozy condo with WiFi, fitness room in enjoyable Laconia

Cozy condo with WiFi, fitness room in enjoyable Laconia
Weirs Beach
9.4 out of 10, Exceptional, (8 reviews)
"The condo was clean and much larger than expected! We had a wonderful stay! "
United States
Beth M.
The price is AED 476
AED 1,178 total
includes taxes & fees
14 Sep - 15 Sep
Cozy condo with WiFi, fitness room in enjoyable Laconia
Exterior

15. Lake View Cedar Lodge Room w/ Private Balcony

Lake View Cedar Lodge Room w/ Private Balcony
Weirs Beach
9.4 out of 10, Exceptional, (20 reviews)
"Clean, convenient, and comfortable. I was very happy with my stay and would definitely recommend this place!"
United States
Rider
The price is AED 481
AED 960 total
includes taxes & fees
14 Sep - 15 Sep
Lake View Cedar Lodge Room w/ Private Balcony
Beach

16. Lake Getaway: Walk Across Street to Private Beach!

Lake Getaway: Walk Across Street to Private Beach!
Gilford
9.4 out of 10, Exceptional, (26 reviews)
"Nice property and great location "
United States
William R.
The price is AED 382
AED 984 total
includes taxes & fees
17 Aug - 18 Aug
Lake Getaway: Walk Across Street to Private Beach!
Property grounds

17. Lake Kanasatka - Private beach access. Your perfect vacation starts right here!

Lake Kanasatka - Private beach access. Your perfect vacation starts right here!
Moultonborough
9.8 out of 10, Exceptional, (10 reviews)
"Absolute amazing weekend. The host was extremely helpful in telling you where all the items were in the welcome packet. House is very well furnished super clean. I had a wonderful snowmobile weekend will definitely rent this property again!"
United States
David H.
The price is AED 1,010
AED 1,937 total
includes taxes & fees
31 Aug - 1 Sep
Lake Kanasatka - Private beach access. Your perfect vacation starts right here!
Interior

18. Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
Laconia
10.0 out of 10, Exceptional, (28 reviews)
"Easy process and great location"
United States
Daniel
The price is AED 624
AED 1,323 total
includes taxes & fees
17 Aug - 18 Aug
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain
Beach

19. Lakeside Cabin 7 with Kitchen

Lakeside Cabin 7 with Kitchen
Holderness
The price is AED 1,095
AED 1,953 total
includes taxes & fees
25 Aug - 26 Aug
Lakeside Cabin 7 with Kitchen
Marina

20. 2 Bdrm Condo walking distance to Weirs Beach and much more!!

2 Bdrm Condo walking distance to Weirs Beach and much more!!
Weirs Beach
9.6 out of 10, Exceptional, (58 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
The price is AED 735
AED 1,485 total
includes taxes & fees
14 Sep - 15 Sep
2 Bdrm Condo walking distance to Weirs Beach and much more!!
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

The Naswa Resort

The Naswa Resort

10/10 Excellent
"Basically, every thing was perfect,"
Wayne 2-night trip
Posted 7 hours ago
The Naswa Resort

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?

Beautiful and wonderful location. Premier lVRBO host.: This vacation home rental outside of Winona is located on the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Winnipesaukee and Lake Waukewan.

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.