Winona Vacation Rentals

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Vacation Rentals in Winona

Cold Spring Resort
3.5 star property
9.0 out of 10, Wonderful, (85)
"I wish I knew about the property when my kids were younger "
Cold Spring Resort
Easiest location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
10.0 out of 10, Exceptional, (18)
"Chris was great. Home was great location and clean and so much room to spread out! Communication was amazing!"
Easiest location! Rent a Boat, Attend a Wedding! 2600sqft on Main St Meredith
Rustic cottage in private location - Pet friendly!
9.8 out of 10, Exceptional, (89)
"This was an awesome place to stay and unwind. John was a great host and helped us get settled in quickly. It was nice that he provided a boat, kayak, and paddle boat to enjoy the river with. This location is very quiet and relaxing. All the conveniences of a small town are just a short easy drive away. I would recommend this vacation spot to anyone."
Rustic cottage in private location - Pet friendly!
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Dog-friendly home with a pool table, washer/dryer, firepit & beach access
9.0 out of 10, Wonderful, (4)
"We stayed her with our five kids and a dog. The place had a great game room set away from the living room for our three teenage boys to hang out in and be boys. The girls had the living room so plenty of space when they needed a break from each other. It was pretty expensive tho. Figured it would be nice to have toilet paper, some dishwasher tabs, paper towels...basic stuff that most vrbo homes to start out with. All in all it good stay."
Dog-friendly home with a pool table, washer/dryer, firepit & beach access
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (148)
"Hi Malini, Thank you so much for a wonderful stay! It was exactly what we wanted/needed for the weekend. Cheers, Gabe"
The price is CA $1,638
CA $3,290 total
includes taxes & fees
Jun 4 - Jun 5
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
White Mountain Cozy Cottage with Touch of Modern
9.8 out of 10, Exceptional, (28)
"Overall, we enjoyed our stay. We were delighted to find the beautiful Pemi River just minutes away via a short walk through the woods adjacent to the property. It was an unseasonably warm and wet winter weekend, and the driveway / parking areas were muddy, so just a bit of a warning for other guests to expect this."
The price is CA $258
CA $463 total
includes taxes & fees
Jun 16 - Jun 17
White Mountain Cozy Cottage with Touch of Modern
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
9.0 out of 10, Wonderful, (16)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
Amazing lakefront retreat with fireplace & stunning views - near skiing & golf
Amazing lakefront retreat with fireplace & stunning views - near skiing & golf
Waterfront Ashland Home ~ 2 Mi to Downtown!
9.6 out of 10, Exceptional, (4)
"My familly stayed at the property for a wedding in Meredith and the location and proximity to the wedding venue was perfect. The house is huge, clean, provides every amenity imaginable and the deck and waterfront setting was ideal for a family gathering. We enjoyed having plenty of room to cook and eat together, sit out on the deck and converse and ended each evening around the fire pit with s'mores! This property is perfect for a quiet famiy gathering but I would not recommend it for a large...
Waterfront Ashland Home ~ 2 Mi to Downtown!
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
9.6 out of 10, Exceptional, (119)
"If you are seeing a concert at Bank of NH pavilion, look no further. Venue is a quick walk (no more then 10 minutes) on a tiny, lit path behind the motel. Steps away from a gorgeous beach with chairs provided. We were so happy we came a day early to enjoy it. Lake view from the balcony. Place was not fancy by any means but very clean and had everything you may need. We will be back!"
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
Vrbo Property
7.4 out of 10, Good, (3)
"Great lake access. The house was in a good location. The house needs a little TLC."
Vrbo Property
Fully renovated, dog-friendly home with private beach access & golf nearby
8.8 out of 10, Excellent, (3)
"Outdoor deck was not safe especially the steps leading to deck. The house was clean and exactly as it appeared on site. Not enough towels or toilet paper for 7 people. We had to run out and purchase toilet paper, only 2 already opened rolls were at property. Overall a beautiful place and neighborhood. Would definitely stay again."
Fully renovated, dog-friendly home with private beach access & golf nearby
Beautiful cottage in the Lakes Region on Hermit Lake
10.0 out of 10, Exceptional, (6)
"Gray stay! Central to 93 N to get up the the White Mountains and about 30 minutes from the major lake towns. Beautiful property!"
Beautiful cottage in the Lakes Region on Hermit Lake
Lakefront & ski retreat with wrap-around deck, wood fireplace, & private beach
10.0 out of 10, Exceptional, (1)
Lakefront & ski retreat with wrap-around deck, wood fireplace, & private beach
My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷
10.0 out of 10, Exceptional, (5)
"Our group really enjoyed the large house and balcony. It was comfortable cooking in the kitchen, especially with the island for surface space. The living room library and movie selections and nearby community center was a plus as well. Josh was an excellent host."
My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷
Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates
9.4 out of 10, Exceptional, (190)
"The house is beautifully located with amazing views. De house is well organized and had everything we needed. Highly recommend staying here. The owner was very attentive."
Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates
Cozy Lake Retreat: Shell Camp Lake Couples get way. Centrally located
10.0 out of 10, Exceptional, (27)
"Lisa is a spectacular host and her property was gorgeous! My boyfriend, pup and I had a quiet, relaxing getaway from our busy lives. We walked the neighborhood and enjoyed the views of the pond. I wish we had stayed longer, but we would definitely come back! Thank you again!! 😊"
The price is CA $224
CA $386 total
includes taxes & fees
May 31 - Jun 1
Cozy Lake Retreat: Shell Camp Lake Couples get way. Centrally located
Gorgeous Waterfront Condo with Lake Access & Views
10.0 out of 10, Exceptional, (15)
"We loved our stay at this cozy home. My husband and I stayed there for six nights. they were very accommodating to our needs . the house had everything we needed. It s two bedrooms, two baths was the perfect size for us . We were able to have meals and cook or go out to each. in a wonderful fireplace. Beautiful views. Everything we needed was close . We would definitely stay here again. Thank you to Rahna and staff. Awesome!"
The price is CA $185
CA $467 total
includes taxes & fees
Jun 3 - Jun 4
Gorgeous Waterfront Condo with Lake Access & Views
Lake Winnipesaukee, Boat Dock, Hot Tub and Game Room
10.0 out of 10, Exceptional, (2)
"Amazing house, host & location. Great proximity to Gunstock."
Lake Winnipesaukee, Boat Dock, Hot Tub and Game Room
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
10.0 out of 10, Exceptional, (138)
"The Meredith Cottage is an oasis away from home. The owners have considered all the details and amenities one needs while staying there. The house is very well stocked, beautifully decorated and comfortable. Location is walking distance to great shops and restaurants. Highly recommend!"
The price is CA $547
CA $1,020 total
includes taxes & fees
Jun 27 - Jun 28
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
Don't see what you're looking for?
See all available properties in Winona
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.

Other types of properties in Winona you may be interested in

Mill Falls at the Lake
3.0 star property
8.2 out of 10, Very good, (512)
"We had a wonderful time!"
The price is CA $207
CA $279 total
includes taxes & fees
Jun 26 - Jun 27
Mill Falls at the Lake
Fireside Inn & Suites Gilford
2.5 star property
8.8 out of 10, Excellent, (551)
"Easy drive to stores and restaurants"
The price is CA $180
CA $195 total
includes taxes & fees
Jun 2 - Jun 3
Fireside Inn & Suites Gilford
Best Western Plymouth Inn-White Mountains
2.5 star property
9.0 out of 10, Wonderful, (513)
"My family and I stayed here for 1-night enroute to a vacation in northern New Hampshire. We were quite pleased with this hotel, clean, reasonably priced, and friendly staff. The breakfast was nice, better than typically found in an American chain hotel. My family and I agreed that we would happily stay here, again, if we needed a 1- or 2-night stay in the area."
The price is CA $150
CA $163 total
includes taxes & fees
Jun 4 - Jun 5
Best Western Plymouth Inn-White Mountains
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.

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

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

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we have vacation rentals close to top sights in Winona, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Winona has to offer?

Dog-friendly home with a pool table, washer/dryer, firepit & beach access: This vacation home rental outside of Winona is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the pool table in this rental home to help you unwind.

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 larger area, you’ll find Lake Winnipesaukee and Winnipesaukee Playhouse.

What’s a vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.

Recent reviews of Winona properties
Expedia verified reviews