Holiday Rentals in Winona

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Winona

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (157)
"The location is exceptional. The pool area, steam room, sauna, and total recreation area were amazing. The pool temperature (air and water) was good for this time of year. The consistent 4 foot pool depth made it great for a community water volley ball game. (*We are all over 65) Having 5 "king bedrooms with three bathrooms in three different areas of the house allowed the entire adult group comfort and privacy. We also made use of the 2 bathrooms near the pool. The extra large living...
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Spacious Belmont Home w/ Seasonal Pool & Grill!
9.0 out of 10, Wonderful, (65)
"We had an amazing experience here! From booking to check-in to the weekend stay, everything was smooth and easy. Robert was excellent with answering questions, allowing an early check-in and an extended checkout, and was very responsive with communication. I met property managers Brandon, Jared, and Craig when I arrived and they were super helpful (and gave a great pizza delivery recommendation)! The house was exactly as advertised. Plenty of space for our group, clean and organized, and...
Spacious Belmont Home w/ Seasonal Pool & Grill!
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
8.8 out of 10, Excellent, (19)
"Great time."
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, Cable TV & Internet
Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates
9.6 out of 10, Exceptional, (204)
"Have a wonderful stay. It was great waking up every morning to mountain views. "
Spacious Mtn Top Contemporary - Spectacular Views - in Waterville Estates
My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷
9.8 out of 10, Exceptional, (9)
"Had a fun weekend with friends and Family. The house had everything that we need. The views are amazing. Thank you Joshua for hosting us. "
My Mountainside Mansion in Waterville Estates!🏔☀️🏊‍♀️⛷
Cozy, Pet-Friendly Escape Near Lake & Mountains
10.0 out of 10, Exceptional, (23)
"Beautiful home. Great weekend away!! "
Cozy, Pet-Friendly Escape Near Lake & Mountains
Cold Spring Resort
3.5 star property
9.0 out of 10, Wonderful, (98)
"2 level condo is nice. A little tricky to find in the dark. Arrive in the daylight or get additional details than what’s on the “map” at check in."
Cold Spring Resort
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
8.8 out of 10, Excellent, (15)
"We stay. In Alton Bay each year for a couple of concerts at Bank of NH Pavilion in Gilford. We extend it by staying for a couple of days at Lake Winnipesaukee The motel is perfectly located close to the venue and on the lake for swimming and boating while visiting BNH Pavilion. The motel is in a pine grove and is lake front. It's "!old school " feel reminds of my childhood. It's clean and quite, but no thrills. Don't expect first class accommodations but if you like the feel of a...
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
8.6 out of 10, Excellent, (24)
"Nice home, close to bank of NH pavilion, and Weirs beach. "
Stargazer's retreat with hot tub & decks - near Ellacoya State Beach
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
10.0 out of 10, Exceptional, (7)
"Great location, beautiful house , we were a bit upset that the outside hot tub was not available even though it was listed as part of the amenities."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Modern masterpiece on Squam featured in Dwell and Boston Magazine
10.0 out of 10, Exceptional, (70)
"We enjoyed three nights in this beautiful home on Squam Lake. Nestled in the pine forest on the edge of the Lake, it affords beautiful views of the surrounds. However, it is the house that is the winner. Beautifully and creatively designed and fully equipped, with a wonderful kitchen, we thoroughly enjoyed our stay. "
Modern masterpiece on Squam featured in Dwell and Boston Magazine
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D
6.8 out of 10, (9)
"I didn’t look close at the on-line pics so at first arrival I had concerns. It’s a charming older style lake house that could use a bit of pampering but it was very clean and comfortable for our group of 8. The host and management company were great and easy to communicate with. We came up for our daughter’s wedding and we all had a very nice weekend. Thank you"
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK
9.0 out of 10, Wonderful, (8)
"The house was clean and comfortable. It was roomy. The views were great. The owners were helpful and friendly. We would stay here again. "
4Bedrm Sleeps 12 Winnipesaukee Waterfront gradual sandy sloped shoreline Pets OK
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
10.0 out of 10, Exceptional, (160)
"Wouldn’t change a thing! The house was wonderful and Sharon was amazing. Had a great vacation and would definitely stay here again."
Custom Cottage Historic Meredith Village,walk to restaurants, shops Dog welcome
Serene Retreat near Lake Winnipesaukee with Hot Tub & Modern Amenities
9.4 out of 10, Exceptional, (10)
"Big house, clean, full furnished, comfortable bed, hot tub is great! love this place, will come back again"
Serene Retreat near Lake Winnipesaukee with Hot Tub & Modern Amenities
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
10.0 out of 10, Exceptional, (86)
"Hanna was a wonderful host! When we had an issue with water pressure in the shower, she responded within minutes and had someone out to fix it within about an hour. The place is rustic but charming with a great fireplace!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Waterfront Ashland Home ~ 2 Mi to Downtown!
8.4 out of 10, Very good, (7)
"We stayed for a short family vacation. The house was just as pictured. Everything we needed was supplied. The kids loved swimming and fishing right were we stayed!"
Waterfront Ashland Home ~ 2 Mi to Downtown!
Winnipesaukee Lakefront Home with Dock & Views!
9.4 out of 10, Exceptional, (61)
"Interior of the home was very nice. Access to water was difficult and made worse by the lack of pruning of the bushes that had grown into the already narrow stairway leading to the dock. Parking was difficult, additional information regarding possible places to park another vehicle or trailer would be helpful. A broom and functioning vaccum would also have been helpful. Dock boards, posts, and cletes, were loose in multiple locations with exposed nails facing upwards. Multiple dirty dishes in...
Winnipesaukee Lakefront Home with Dock & Views!
Cozy Cottage on Lake Winni
9.2 out of 10, Wonderful, (33)
"This cabin was close to most attractions in the area. The cabin was clean and was perfect for our stay!"
Cozy Cottage on Lake Winni
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
9.6 out of 10, Exceptional, (131)
"We really enjoyed our stay. The condo was comfortable, clean, had everything you needed and was in a great location. We enjoyed walking across the street to the lake and up the hill to go the concert next door. We were also a short drive from Weirs Beach. We had great communication and hope to stay there again."
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock
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.
Don't see what you're looking for?
See all available properties in Winona
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Winona you may be interested in

Best Western Plymouth Inn-White Mountains
2.5 star property
9.0 out of 10, Wonderful, (685)
"It was all wonderful!!"
The price is €98
includes taxes & fees
27 Nov - 28 Nov
Best Western Plymouth Inn-White Mountains
Steele Hill Resorts
3.0 star property
8.4 out of 10, Very good, (573)
"Beautiful place"
The price is €164
includes taxes & fees
24 Nov - 25 Nov
Steele Hill Resorts
Best Western Plus Landmark Inn
2.5 star property
7.6 out of 10, Good, (956)
"Convenient "
The price is €105
includes taxes & fees
3 Dec - 4 Dec
Best Western Plus Landmark Inn
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.

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Winona is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Winnipesaukee Playhouse and Little Squam Lake.

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.