Montgomery Cottages - Vacation Rentals in Winona

LAKEFRONT 3 BDRM, 2 LOFTS, BEACH, DOCK, close to town From US $451
         

Luxury Places to Stay in Winona

Over 74+ Luxury Places to Stay in or Near Winona
1/4 Acre Woods on Lake Waukewan! From US $1,043
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hot Tub and Walk to Lakeside Dining Meredith Home! From US $1,005
         

Kayak, walk or swim to Meredith town center From US $781
         

10.0 (24 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Seven Gables Farm! Gorgeous home near Lake Waukewan! From US $778
         

60 Shades of Water, Lake Waukewan Waterfront From US $764
         

9.8 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Winona

Over 2+ Top-Rated Vacation Rentals with a Pool in or Near Winona
Mill Falls Resort Collection at the Lake From US $192
         

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8.4 (911 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Mill Falls Resort Collection at the Lake From US $568
         

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7.5 (366 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Winona

Over 23+ Pet-Friendly Vacation Rentals in or Near Winona
Kayaks, kids secret room, fishing, fire pit, ev charger. From US $399
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Pet Friendly Escape to Lake Waukewan for Your Next Getaway From US $611
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Meredith Bay Views in the heart of Downtown! Home in Meredith, NH. From US $729
         

3-bedroom house in charming Meredith with WiFi, AC. Enjoy your stay From US $279
         

Downtown Meredith Hideaway! Lake Winnipesaukee and Lake Waukewan! From US $202
         

See More Pet-Friendly Vacation Rentals in Winona on PetFriendly.io

Large Vacation Homes & Villas in Winona

Over 18+ Large Vacation Homes & Villas in or Near Winona
Hot Tub + Walk to Lakeside Dining: Meredith Home! From US $552
         

Historic Meredith Home Walk to Town Center! From US $592
         

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7.8 (6 Reviews)
House
  • Parking
  • Accessibility
  • Security/Safety
Ski Season is Coming! 4-BR, Sleeps 14, Large Yard From US $434
         

Historic Meredith Home: Walk to Town Center! From US $310
         

8.0 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Wheelchair Accessible Vacation Homes in Winona

Over 2+ Wheelchair Accessible Vacation Homes in or Near Winona
Charming Meredith Village Antique Brick Home For Rent From US $179
         

4.5 (30 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Meredith Home - Walk to Lakes and Restaurants! From US $454
         

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1.0 (1 Review)
Apartment
  • Parking
  • View
  • Wheelchair Accessible

Winona Varoom and Airbnb Places to Stay Under $200

Over 9+ Winona Varoom and Airbnb Places to Stay Under $200
Serenity of the Lake From US $134
         

9.6 (34 Reviews)
Cabin
  • Parking
  • TV
  • View
Berta's Lake Front Cottage on Winona Lake! From US $186
         

New
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Tuckernuck Inn From US $195
         

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9.2 (99 Reviews)
Bed & Breakfast
  • Parking
  • Security/Safety
  • Guest Services
Luxurious and Sunny Apt at Main Street, Meredith From US $150
         

10.0 (15 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Completely renovated house near lake From US $145
         

9.4 (6 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Bedding/Linens
Time for Hygge at Downtown Meredith From US $142
         

5.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Kitchen

Instantly Bookable Vacation Homes in Winona

Over 17+ Instantly Bookable Vacation Homes in or Near Winona
Uptown Charmer, Meredith near Winnipesaukee! From US $343
         

9.4 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Peaceful Meredith Getaway - 2 BR w/Wifi & Charm From US $707
         

7.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Cozy Corners Meredith Home - With Wifi From US $463
         

About Winona Vacation Rentals

With more than 6 Winona vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winona.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Winona, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winona. Places to stay near Winona are 607.5 ft² on average, with prices averaging $275 a night.

Montgomerycottages makes it easy and safe to find and compare vacation rentals in Winona with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winona

Type Count
Cottages 6

Use these Quick Filters to Find a Vacation Rental in Winona

Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winona.

Weather in Winona

View the weather forecast for Winona before booking your Winona Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F