Default HTG hotel image

Winona Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winona holiday rentals

A row of brown single-story buildings with a parking lot in front.

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (271 reviews)
"Had a great weekend stay."
United States
Armand
The price is HK$1,038
HK$1,127 total
includes taxes & fees
27 Oct - 28 Oct
Cold Spring Plymouth Resort
A lakeside view with a boat on the water, a table with chairs, and a tent.

2. 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 HK$1,703
HK$3,065 total
includes taxes & fees
7 Oct - 8 Oct
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
A two-story house with a covered porch and a small deck.

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, (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 HK$1,596
HK$2,915 total
includes taxes & fees
5 Oct - 6 Oct
Meredith Bay - Brand New 1st Floor Apartment In Private Home
A wooden cabin with a hot tub and a deck area.

4. 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, (5 reviews)
"Place was clean and nice. "
United States
Bryan K.
The price is HK$3,609
HK$7,347 total
includes taxes & fees
6 Oct - 7 Oct
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!
A wooden cabin with a hot tub and a deck area.

5. 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$1,841
HK$3,453 total
includes taxes & fees
26 Oct - 27 Oct
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.
A spacious living area with a dining table, chairs, and a sofa.

6. Spacious Lakes Region Retreat—Game Room & Gazebo

Spacious Lakes Region Retreat—Game Room & Gazebo
Meredith
9.6 out of 10, Exceptional, (10 reviews)
"House was immaculate with all the amenities we needed. Beautiful home."
United States
Bernadette M.
The price is HK$5,210
HK$10,344 total
includes taxes & fees
4 Oct - 5 Oct
Spacious Lakes Region Retreat—Game Room & Gazebo
A beach with clear water, a dock, and boats.

7. 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$4,336 total
includes taxes & fees
12 Oct - 13 Oct
Bear Cub Cabin- Waterfront Cabin
A hotel with a swimming pool, solar panels, and a parking lot.

8. 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 HK$863
HK$1,916 total
includes taxes & fees
9 Oct - 10 Oct
Cedar Lodge Condo w/ Loft and private balcony
A lakeside cabin with a dock, surrounded by dense trees and a sandy beach area with lounge chairs.

9. 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$2,494
HK$3,586 total
includes taxes & fees
12 Oct - 13 Oct
Squam waterfront 2 bed 2 bath (Suite 8)
A beach with three wooden lounge chairs facing a lake, surrounded by trees.

10. Squam Suite - Waterfront

Squam Suite - Waterfront
Holderness
10.0 out of 10, Exceptional, (2 reviews)
"Great stay here. What an amazing place!"
United States
Gib J.
The price is HK$2,494
HK$3,586 total
includes taxes & fees
12 Oct - 13 Oct
Squam Suite - Waterfront
A beach with boats, a sandy shore, and a clear sky.

11. 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 HK$1,426
HK$3,523 total
includes taxes & fees
6 Oct - 7 Oct
Newly Renovated June 2026 2BR/2BA Laconia Condo with AC & WiFi
A beach with three wooden lounge chairs facing a lake, surrounded by trees.

12. 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$4,722 total
includes taxes & fees
12 Oct - 13 Oct
Squam Lake 3 bed 3 bath (Suite #7)
A large building with multiple sections, surrounded by snow-covered ground and trees, overlooking a large body of water.

13. Cedar Lodge condo with mountain & lake Winnipesauke views!

Cedar Lodge condo with mountain & lake Winnipesauke views!
Weirs Beach
9.2 out of 10, Wonderful, (58 reviews)
"The room was adequate. Clean but not superclean!"
United States
Walter
The price is HK$1,165
HK$2,279 total
includes taxes & fees
4 Oct - 5 Oct
Cedar Lodge condo with mountain & lake Winnipesauke views!
A beach with three wooden lounge chairs facing a lake, surrounded by trees.

14. Loon Lodge - Waterfront Cabin

Loon Lodge - Waterfront Cabin
Holderness
8.0 out of 10, Very good, (2 reviews)
"Absolutely stunning views"
United States
kathy t.
The price is HK$3,107
HK$4,336 total
includes taxes & fees
12 Oct - 13 Oct
Loon Lodge - Waterfront Cabin
A lakeside property with a sandy beach, a wooden dock, and a building with a balcony overlooking the water.

15. Squam waterfront 2 bed 2bath (Suite 9)

Squam waterfront 2 bed 2bath (Suite 9)
Holderness
10.0 out of 10, Exceptional, (1 review)
"The only thing i was disappointed that going down to lake was impossible for me as i am handcaped i wish it was more accessible to me . If it was i wouls stay there next year too "
United States
Pam D.
The price is HK$2,494
HK$3,586 total
includes taxes & fees
12 Oct - 13 Oct
Squam waterfront 2 bed 2bath (Suite 9)
A beach with clear water, a dock, and boats.

16. Waterfront 2 bedroom 2 bath at Squam (Suite 11)

Waterfront 2 bedroom 2 bath at Squam (Suite 11)
Holderness
8.4 out of 10, Very good, (6 reviews)
"Thanks so much for hosting us! we have been coming to squam for 20+ years and never stayed at the boulders. The space was great for the price and right on the lake. We had no issues whatsoever and would highly recommend for anyone looking for a cabin type weekend by the water. "
United States
Anonymous traveller
The price is HK$2,494
HK$3,499 total
includes taxes & fees
13 Oct - 14 Oct
Waterfront 2 bedroom 2 bath at Squam (Suite 11)
A living room with a gray sectional sofa, a coffee table with decorative items, a painting on the wall, and a dining area with a wooden table and chairs.

17. Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Sanbornton
10.0 out of 10, Exceptional, (19 reviews)
"Great place for the extended family getaway. Clean, great location and has all the essentials you need.We had a great time with our teenage and young adults kids for NYE."
United States
Valerie A.
The price is HK$2,472
HK$5,738 total
includes taxes & fees
2 Oct - 3 Oct
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
A waterfront town with a large ferry dock, residential buildings, and a marina.

18. 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, (60 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
2 Bdrm Condo walking distance to Weirs Beach and much more!!
A lakeside seating area with chairs and a fire pit, surrounded by trees and a view of the lake.

19. Waterfront home on Squam Lake

Waterfront home on Squam Lake
Holderness
9.6 out of 10, Exceptional, (4 reviews)
"The location was amazing! We were 9 people with 4 kids ages 4-14 and two grandparents. The beach and its amenities (kayaks, canoes, fire pits, sand toys) made our stay well worth it and had something for all ages to enjoy. Kyle was available at a moments notice to provide anything we needed. "
United States
Christina M.
The price is HK$5,610
HK$7,859 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront home on Squam Lake
A beach with clear water, a dock, and boats.

20. Waterfront 2 bedroom on Squam (Suite 12)

Waterfront 2 bedroom on Squam (Suite 12)
Holderness
8.8 out of 10, Excellent, (6 reviews)
"We loved our little getaway here! "
United States
Kelsey P.
The price is HK$2,494
HK$3,499 total
includes taxes & fees
12 Oct - 13 Oct
Waterfront 2 bedroom on Squam (Suite 12)
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winona Hotel Reviews

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

8/10 Good
"The woman at the front desk was really nice! The room itself was pretty good. The bathroom could have been cleaned a bit better but the main part of the room was clean. We did use the pool as well and that was a nice space. We would stay again!"
Julia 1-night trip
Posted 1 day ago
Best Western Plus Landmark Inn

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?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This holiday home rental outside of Winona is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games 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.