Holiday Rentals in Winona

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Holiday Rentals in Winona

Cold Spring Plymouth Resort

3.5 star property
9.0 out of 10, Wonderful, (139)
"Perfect place for a family vacation in New Hampshire "
Cold Spring Plymouth Resort

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

9.8 out of 10, Exceptional, (175)
"Fantastic stay! The house was spotless, beautifully decorated, and had all the amenities we needed for a comfortable stay. The location was perfect—close to everything yet peaceful and relaxing. The host was responsive and made the check-in process seamless. Highly recommend and would definitely stay again!"
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

great location weirs beach area rental

9.4 out of 10, Exceptional, (21)
"The property was exactly as it was listed, The host was great"
The price is €393
includes taxes & fees
27 Aug - 28 Aug
great location weirs beach area rental

Best value on Newfound Lake NH 2 day min

9.2 out of 10, Wonderful, (21)
"We had a great time staying at this house. The house was clean, had plenty of room for everyone in the group, and was a great location. "
The price is €331
includes taxes & fees
2 Sept - 3 Sept
Best value on Newfound Lake NH 2 day min

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is €273
includes taxes & fees
1 Sept - 2 Sept
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

9.4 out of 10, Exceptional, (139)
"Everything was clean & convenient. Such a beautiful beach also! "
Misty Harbor Resort, walk to concerts at NH Bank Pavilion beach on Lake Winni.

Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

10.0 out of 10, Exceptional, (54)
"This property is beautifully situated on a peninsula with a great beach and large dock. The management was very easy to communicate with and made the check-in/check-out process extremely guest friendly. Great for large groups as each bedroom essentially has its own bathroom."
Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

Stunning lakefront gem with full water view, beach access & dock

10.0 out of 10, Exceptional, (11)
"A perfect little cottage for a getaway for two, to the lake. Great experience and would happily return someday."
Stunning lakefront gem with full water view, beach access & dock

Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates

9.6 out of 10, Exceptional, (223)
"Cozy cabin with great privacy and great views for a large group. "
Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates

Secluded cozy Waterfront - Dams Beach

9.0 out of 10, Wonderful, (44)
"I came for Laconia bike week, and it was the perfect spot to be close to the action but also retreat when needed! Very relaxing and host was very accommodating!"
Secluded cozy Waterfront - Dams Beach

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

9.0 out of 10, Wonderful, (21)
"Excellent"
The price is €247
includes taxes & fees
1 Sept - 2 Sept
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6

9.2 out of 10, Wonderful, (25)
"This lovely lake house was right in the middle of our 5 other relatives' lake houses. We have been going to this lake community for many years & staying with relatives, but we wanted to rent our own place this time. The house was very clean & well-appointed, & we really enjoyed our stay there. The brook was directly outside in back! The weather was a bit cool, so we didnt kayak or go to the beautiful beach, but that made for more family time with our 30 relatives!"
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6

Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

10.0 out of 10, Exceptional, (12)
"Great place to stay. Was the perfect spot to git the white mountains/conway. While also being super close to the pavilion to take in a concert. Would definitely stay here again/recommend!"
Come & enjoy beautiful Lake Winni! Concerts are within 5 min. Economy pricing

White Mountain Cozy Cottage with Touch of Modern

9.6 out of 10, Exceptional, (44)
"Great stay in the NH white mountains! Really enjoyed our stay! Check in and check out process was very easy. Would stay again. "
White Mountain Cozy Cottage with Touch of Modern

🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊

9.6 out of 10, Exceptional, (21)
"What a unique and fun stay! The use of the property is really the gem here, Beautiful clean property that checks all the boxes! "
🌟 Unique Houseboat Experience on Lake Winnipesaukee - Harborside 🚤🌊

The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

10.0 out of 10, Exceptional, (15)
"Great cottage right by the lake. Host was incredibly responsive and helpful. Fun back yard for games and grilling. 5/5 would recommend a stay here!"
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

10.0 out of 10, Exceptional, (179)
"Amazing property and great location. The host could not have been nicer- we will be back! "
Walk to wedding venues, shops, dining, hiking, movies, ice cream & dog friendly.

The Gnome Home Cottage located near white mountain NH

9.6 out of 10, Exceptional, (49)
"enjoyed my stay. Property was in a great location and everything was as advertised. "
The price is €267
includes taxes & fees
2 Sept - 3 Sept
The Gnome Home Cottage located near white mountain NH

4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

8.6 out of 10, Excellent, (9)
"Loved the place. Shallow beach was perfect for the kids and the dock was great for our boat. Plenty of beds for everyone and the ping pong table was a big hit. Communication from the property manager was easy and helpful."
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.

9.6 out of 10, Exceptional, (20)
"As advertised and more. Terrific place."
Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.
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

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as €247 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cold Spring Plymouth Resort: This holiday home rental outside of Winona is located in the mountains, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. You can relax into your holiday with an outdoor tennis court and 1 hot tub.

What’s there to see and do in Winona?

Lake Waukewan and Winona Lake are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Lake Winnipesaukee and Winnipesaukee Playhouse.

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.