Winona holiday rentals

We found 715 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Winona to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, which might include parking and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Winona

Showing deals for:1 Jan - 8 Jan

First floor en suite
Back of house from dock
Living area
Porch
Exceptional
(39 reviews)

Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 10

Sanbornton

8% off
AU$9,835
for 7 nights, 1 home
AU$1,405 per night
includes taxes & fees
Gorgeous Waterfront with Dock & Mountain Views on Winnisquam - Sleeps 10
Dining
Exterior
Living area
Private kitchen
Exceptional
(27 reviews)

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Laconia

8% off
AU$19,379
for 7 nights, 1 home
AU$2,768 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(10 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
AU$10,879
for 7 nights, 1 home
AU$1,554 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
Living area
Gather by the Firepit
Living area
Exterior
Wonderful
(51 reviews)

Lake House Private Waterfront - Lake & Beach life in Winnipesaukee

Laconia

8% off
AU$8,758
for 7 nights, 1 home
AU$1,251 per night
includes taxes & fees
Lake House Private Waterfront - Lake & Beach life in Winnipesaukee
Fall colors overlooking the lake from the deck October 2022
Sunroom 4 Season
Private kitchen
Awesome guest sent photo of vase and flowers they bought for dining room table.
Exceptional
(26 reviews)

Kayak, walk or swim to Meredith town center

Meredith

8% off
AU$10,177
for 7 nights, 1 home
AU$1,454 per night
includes taxes & fees
Kayak, walk or swim to Meredith town center
View of the house from the beach.
Comfy seats around one of two fire pits.
Exterior
Interior
Exceptional
(190 reviews)

Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey

Moultonborough

8% off
AU$4,221
for 7 nights, 1 home
AU$603 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Exterior
Living area
1000020392.jpg lower level shops and restaurants
Private kitchen
Excellent
(54 reviews)

Condo at Paugus Bay. Pool area. Near Weirs Bch,Gunstock mtn, NH Bank Pavillion.

Gilford

8% off
AU$1,790
for 7 nights, 1 apartment
AU$256 per night
includes taxes & fees
Condo at Paugus Bay. Pool area. Near Weirs Bch,Gunstock mtn, NH Bank Pavillion.
Side garden
sunroom
View of house from driveway.
Living room
Exceptional
(60 reviews)

NH Mountain Getaway! Secluded Location Near Squam Lake

Holderness

8% off
AU$3,247
for 7 nights, 1 home
AU$464 per night
includes taxes & fees
NH Mountain Getaway! Secluded Location Near Squam Lake
Living area
Pool
Property grounds
Property grounds
Exceptional
(11 reviews)

4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7

Laconia

7% off
AU$2,290
for 7 nights, 1 home
AU$327 per night
includes taxes & fees
4-Season Lake Winni Townhome + Dock, Pool, Hiking + Slopes + Sleeps 7
Bedroom #2 Queen size bed
Walk out to enjoy the beautiful covered deck and beautiful vie of Lake Hermit.
Lighting over kitchen counter
Welcome to you “Home Away from Home”
Exceptional
(305 reviews)

Beautiful and wonderful location. Premier lVRBO host.

Sanbornton

8% off
AU$3,246
for 7 nights, 1 home
AU$464 per night
includes taxes & fees
Beautiful and wonderful location. Premier lVRBO host.
Playing at the beach
View of Pasquanney Bay from our beach
Looking north from our beach
A perfect beach day
Exceptional
(106 reviews)

Camp At Newfound Lake - Lake access

Bristol

9% off
AU$3,526
for 7 nights, 1 home
AU$504 per night
includes taxes & fees
Camp At Newfound Lake - Lake access
Exterior
Marina
Property grounds
Interior
Wonderful
(12 reviews)

Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's

Laconia

8% off
AU$3,203
for 7 nights, 1 apartment
AU$458 per night
includes taxes & fees
Cozy 3-bdrm/2bth condo with balcony, lake views, pool and short walk to Weir's
Living area
Exterior
Dining
Private kitchen
Exceptional
(53 reviews)

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

Meredith

8% off
AU$2,856
for 7 nights, 1 home
AU$408 per night
includes taxes & fees
Meredith Bay - Brand New 1st Floor Apartment In Private Home

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Winona getaway

Learn about the unique charm of Winona with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Winona

Are you looking for attractions to see in the area? Venture out of your holiday home and experience everything that makes Winona a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Cascade Spa (3.2 mi / 5.2 km)
  • Squam Lakes Natural Science Center (4.9 mi / 7.9 km)
  • Kellerhaus (6.1 mi / 9.9 km)
  • Ellacoya State Park (12.1 mi / 19.4 km)
  • Gunstock Mountain Resort (12.9 mi / 20.8 km)
  • Owl's Nest Resort & Golf Club (14.9 mi / 24 km)

Exploring the natural landscape of Winona

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Winona. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Waukewan (1.8 mi / 2.9 km)
  • Little Squam Lake (4.3 mi / 6.9 km)
  • Squam Lake (5.7 mi / 9.2 km)
  • Weirs Beach (6.6 mi / 10.7 km)
  • Paugus Bay (8.3 mi / 13.3 km)
  • Lake Winnisquam (9.7 mi / 15.6 km)

Travelling to and around Winona

Fly into Laconia, NH (LCI-Laconia Municipal), the closest airport, located 9.2 mi (14.8 km) from the city centre.

Frequently asked questions

What is the best area to stay in Winona when booking a holiday rental?
When considering a holiday rental in Winona, New Hampshire, the area around Lake Winona is certainly a top choice. This picturesque neighbourhood offers a serene lakeside experience, superb for those looking to unwind in nature. The local scenery is stunning, with opportunities for swimming, kayaking, and leisurely walks along the shoreline.Another appealing option is the vicinity of the Belknap Mountain Range, where you can find charming properties located in the woods. This area is ideal for outdoor enthusiasts, providing access to numerous hiking trails and breathtaking views from the mountain summits.In terms of attractions, the nearby Weirs Beach is a popular spot, particularly during the summer months, where visitors can enjoy beach activities and the local boardwalk. Additionally, the scenic beauty of the Lake Winnipesaukee region is just a short drive away, offering further recreational options and vibrant local culture.
What are the top attractions in Winona?
In Winona, New Hampshire, visitors can enjoy a range of attractions that showcase the natural beauty and cultural heritage of the area. The stunning Lake Winona is a primary highlight, offering opportunities for boating, swimming, and fishing. The nearby Mount Major provides excellent hiking trails with rewarding views of the lake and surrounding mountains, making it a popular spot for outdoor enthusiasts.In the heart of the region, the charming town of Meredith is just a short drive away and features quaint shops, restaurants, and the scenic Meredith Marina. Additionally, the annual New Hampshire Lakes Region Winter Games draw visitors to partake in seasonal activities like ice fishing and snowshoeing, providing a great experience during the colder months.For those interested in local history, the Winona Historic District offers a glimpse into the area's past with its beautifully preserved architecture and historical landmarks.
Are all fees included in the Winona holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Winona holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winona with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Winona holiday homes?
You can find great discounts on holiday homes in Winona on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Winona holiday home booking on Stayz?
To find Winona holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winona?
A long-stay holiday home in Winona is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Winona holiday home?
Book your Winona holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winona?
Prices for holiday homes in Winona vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winona to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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