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Winona Holiday 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 holiday rentals

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 HK$1,039
HK$1,127 total
includes taxes & fees
7 Sept - 8 Sept
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 HK$6,529
HK$10,864 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.
The price is HK$1,687
HK$3,065 total
includes taxes & fees
2 Sept - 3 Sept
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.
The price is HK$4,133
HK$6,000 total
includes taxes & fees
25 Aug - 26 Aug
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 HK$3,610
HK$7,348 total
includes taxes & fees
13 Sept - 14 Sept
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 traveller
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 HK$549
HK$2,101 total
includes taxes & fees
8 Sept - 9 Sept
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.
The price is HK$6,968
HK$12,371 total
includes taxes & fees
19 Aug - 20 Aug
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 HK$3,271
HK$4,782 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$2,495
HK$3,637 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$3,107
HK$4,396 total
includes taxes & fees
8 Sept - 9 Sept
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 HK$22,395
HK$27,440 total
includes taxes & fees
2 Sept - 3 Sept
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 HK$1,623
HK$3,245 total
includes taxes & fees
15 Sept - 16 Sept
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 HK$975
HK$2,462 total
includes taxes & fees
15 Sept - 16 Sept
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 HK$1,001
HK$2,022 total
includes taxes & fees
15 Sept - 16 Sept
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 HK$816
HK$2,103 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 HK$2,158
HK$4,138 total
includes taxes & fees
31 Aug - 1 Sept
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 HK$1,334
HK$2,818 total
includes taxes & fees
14 Sept - 15 Sept
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 HK$2,338
HK$4,172 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 HK$1,519
HK$3,115 total
includes taxes & fees
15 Sept - 16 Sept
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 8 hours ago
The Naswa Resort

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:

  • View our selection of featured holiday rentals in Winona
  • Use the map to find apartments and other holiday homes in the Winona neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winona while they last

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

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?

Beautiful and wonderful location. Premier lVRBO host.: This holiday home rental outside of Winona is located on the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Winnipesaukee and Lake Waukewan.

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.