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Winona Holiday Rentals

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Our top choices for Winona holiday rentals

1. Cold Spring Plymouth Resort

Cold Spring Plymouth Resort
3.5 star property
Ashland
9.2 out of 10, Wonderful, (261 reviews)
"Had a great weekend stay."
United States
Armand
The price is NZ$257
includes taxes & fees
8 Sept - 9 Sept
Cold Spring Plymouth Resort

2. 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 NZ$524
includes taxes & fees
8 Sept - 9 Sept
Cedar Lodge Condo w/ Loft and private balcony

3. Cute Cedar Lodge Studio with Balcony & Lake Views!

Cute Cedar Lodge Studio with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (20 reviews)
"The room was nice. Great view of the lake."
United States
Brandy a.
The price is NZ$380
includes taxes & fees
22 Sept - 23 Sept
Cute Cedar Lodge Studio with Balcony & Lake Views!

4. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (6 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
The price is NZ$367
includes taxes & fees
16 Sept - 17 Sept
Gilford Perfect Getaway Pool, WIFI & Free Parking

5. Inviting 1BR Lakeview 2nd-Floor | Balcony

Inviting 1BR Lakeview 2nd-Floor | Balcony
Gilford
The price is NZ$495
includes taxes & fees
8 Sept - 9 Sept
Inviting 1BR Lakeview 2nd-Floor | Balcony

6. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is NZ$477
includes taxes & fees
8 Sept - 9 Sept
Cedar Lodge Room 2 Queen Beds & Private Balcony

7. 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, (173 reviews)
"We loved our stay. Very clean and in a great location in Meredith."
United States
Rebecca R.
The price is NZ$684
includes taxes & fees
8 Sept - 9 Sept
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

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

Cedar Lodge condo with mountain & lake Winnipesauke views!
Weirs Beach
9.4 out of 10, Exceptional, (56 reviews)
"The room was adequate. Clean but not superclean!"
United States
Walter
The price is NZ$420
includes taxes & fees
22 Sept - 23 Sept
Cedar Lodge condo with mountain & lake Winnipesauke views!

9. 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, (30 reviews)
"Easy process and great location"
United States
Daniel
The price is NZ$600
includes taxes & fees
8 Sept - 9 Sept
Cozy Studio w/ Pool. Close to Weirs Beach, Concerts,Lake, & Gunstock Mountain

10. 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 NZ$636
includes taxes & fees
21 Sept - 22 Sept
Meredith Bay - Brand New 1st Floor Apartment In Private Home

11. 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, (76 reviews)
"Nice clean place. Easy to get in and out. 10 minute drive to Bank of New Hampshire Pavillion."
United States
Kevin G.
The price is NZ$693
includes taxes & fees
21 Sept - 22 Sept
Spacious 2 Bdrm Condo Walking distance to Weirs Beach!!

12. 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, (31 reviews)
"Perfect property for us right across from the lake Very well decorated and clean The owner was very attentive and answered every question I had! Will definitely be staying there again"
United States
Richard
The price is NZ$410
includes taxes & fees
5 Oct - 6 Oct
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

13. 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, (59 reviews)
"Great location, easy and smooth stay!"
United States
Aimee M.
The price is NZ$705
includes taxes & fees
15 Sept - 16 Sept
2 Bdrm Condo walking distance to Weirs Beach and much more!!

14. Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
The price is NZ$368
includes taxes & fees
21 Sept - 22 Sept
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

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 NZ$422
includes taxes & fees
22 Sept - 23 Sept
Lake View Cedar Lodge Room w/ Private Balcony

16. 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 NZ$757
includes taxes & fees
13 Sept - 14 Sept
Squam Suite - Waterfront

17. 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, (65 reviews)
"Stay was great ! Little small for multiple people but great place for a couple getaway weekend"
United States
Jesse C.
The price is NZ$338
includes taxes & fees
13 Sept - 14 Sept
The Gnome Home Cottage located near white mountain NH

18. 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 NZ$895
includes taxes & fees
20 Sept - 21 Sept
Lakeside Cabin 6 with Kitchen

19. Gorgeous Waterfront Condo with Lake Access & Views

Gorgeous Waterfront Condo with Lake Access & Views
Tilton
9.8 out of 10, Exceptional, (50 reviews)
"Lake View is beautiful and unobstructed inside very clean and inviting keurig and regular coffee maker. Very nice place wish we could’ve stayed longer."
United States
Catherine
The price is NZ$526
includes taxes & fees
21 Sept - 22 Sept
Gorgeous Waterfront Condo with Lake Access & Views

20. Best value on Newfound Lake NH 2 day min

Best value on Newfound Lake NH 2 day min
Bristol
8.8 out of 10, Excellent, (30 reviews)
"Perfect stay! Exactly as described, great little cabin and was perfect for a family weekend "
United States
Kasey C.
The price is NZ$670
includes taxes & fees
1 Oct - 2 Oct
Best value on Newfound Lake NH 2 day min
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

Find out more about Winona

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winona holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winona. 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 Winona. 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 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 holiday 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 Winona short-term rentals, that won’t be hard to do.

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 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.