Winter Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Winter

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
Exterior

Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin

8.6 out of 10, Excellent, (25)
"Everyone was polite and very according definitely going again this summer"
Bucktail Lodge Riverview Cabin on Barker Lake in Winter, Wisconsin
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Property grounds

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

10.0 out of 10, Exceptional, (65)
"Everything you need and more for all ages"
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Smart TV

EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River

10.0 out of 10, Exceptional, (16)
"Beautiful views, beautiful cabins. Great resort bar that is always full of fun people. "
EAGLE LODGE - Cozy Cabin Overlooking the Beautiful E. Fork of the Chippewa River
Telemark Northwoods Lodging
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

Telemark Northwoods Lodging

3.5 star property
9.0 out of 10, Wonderful, (304)
"Perfect lodging option in a wonderful location."
The price is ￥21,787
￥23,857 total
includes taxes & fees
Sep 29 - Sep 30
Telemark Northwoods Lodging
Round Lake Cabin Retreat
TV, fireplace, DVD player, books

Round Lake Cabin Retreat

9.4 out of 10, Exceptional, (72)
"Loves the location and beautiful Round Lake! Our family could all be together and relax with plenty of space!"
Round Lake Cabin Retreat
A-frame Cabin w/ Private Boat Dock!
House (3 Bedrooms) | Interior

A-frame Cabin w/ Private Boat Dock!

3.0 star property
A-frame Cabin w/ Private Boat Dock!
Executive Custom Log Lodge on Little Round Lake
Bar (on property)

Executive Custom Log Lodge on Little Round Lake

10.0 out of 10, Exceptional, (99)
"Great space, well organized. So many options for things to do together as a family. Our large family of 22 people make it an annual trip there. It perfect for us"
Executive Custom Log Lodge on Little Round Lake
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Property grounds

Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

10.0 out of 10, Exceptional, (70)
"Loved our stay for Birkie weekend!"
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Dining

Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

9.6 out of 10, Exceptional, (203)
"It would be difficult to find a cottage with a better lake view than this one. It's our second time here and we love it. Very comfortable in every respect."
The price is ￥19,795
￥50,629 total
includes taxes & fees
Oct 8 - Oct 9
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
Dining

Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward

9.8 out of 10, Exceptional, (113)
"Very nice property on a lake great for paddle boarding. We had a great time."
Lake Hayward. Private Lakefront Within Walking Distance To Downtown Hayward
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Exterior

500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent

9.8 out of 10, Exceptional, (62)
"We had a wonderful time during our stay. The home was excellent for a large family. The waterfront was amazing with a great shoreline."
500' Lakeshore, 2 Docks, Sand Beach, Sleeps 10, A/C, Pontoon Boat for Rent
Modern Cabin located between Grindstone and Lac Courte Oreilles
Outdoor dining

Modern Cabin located between Grindstone and Lac Courte Oreilles

10.0 out of 10, Exceptional, (74)
"The screened porch was amazing"
Modern Cabin located between Grindstone and Lac Courte Oreilles
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Fridge, microwave, oven, stovetop

Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres

10.0 out of 10, Exceptional, (258)
"we enjoyed our 3 night stay hot tube was nice was a chilly rainy snowy weekend fireplace was awesome to sit around stay warm would go back and stay again "
Beautiful Ponderosa Pine Log Cabin - Northwoods Retreat On 10 Acres
Breezy Bay Beach On Round Lake
Smart TV, fireplace, DVD player, books

Breezy Bay Beach On Round Lake

10.0 out of 10, Exceptional, (60)
"We had a week stay with our family at this place and it was perfect! "
Breezy Bay Beach On Round Lake
Cozy Cabin on Secluded Peninsula
Interior

Cozy Cabin on Secluded Peninsula

9.8 out of 10, Exceptional, (42)
"We really enjoyed the stay in the cabin. The location is great and very private."
Cozy Cabin on Secluded Peninsula
Cabin on peaceful soo lake, phillips wi. Enjoy waking up in the great northwood
Dining

Cabin on peaceful soo lake, phillips wi. Enjoy waking up in the great northwood

9.2 out of 10, Wonderful, (7)
"Enjoyed "
Cabin on peaceful soo lake, phillips wi. Enjoy waking up in the great northwood
Grand View Lodge -New Listing With Room For The Family
Dining

Grand View Lodge -New Listing With Room For The Family

9.4 out of 10, Exceptional, (8)
"Over all it was a very nice stay the lake was a little over run with weeds but we enjoyed none the less!"
Grand View Lodge -New Listing With Room For The Family
Lake House & Cottage-2 Docks, Firepits, Kitchens
Terrace/patio

Lake House & Cottage-2 Docks, Firepits, Kitchens

9.8 out of 10, Exceptional, (18)
"The house was perfect for a weekend get away up north!"
Lake House & Cottage-2 Docks, Firepits, Kitchens
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
Smart TV, fireplace, DVD player

Rustic and Charming one Bedroom cabin. Upgraded pontoon!

9.8 out of 10, Exceptional, (96)
"Had a wonderful time in this wonderful cabin! Would stay again!"
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
The Getaway on Grindstone Lake
Exterior

The Getaway on Grindstone Lake

9.8 out of 10, Exceptional, (16)
"clean, cozy cabin. great lake. perfect for a couple"
The Getaway on Grindstone Lake
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 Winter Hotel Reviews

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

10/10 Excellent
"This house is absolutely amazing! Beautiful inside and out. We loved the pool table and shuffleboard in the garage! We also played card games, went fishing on the great pontoon, watched a movie and sports! It rained a bit but there were beautiful rainbows! This was our second stay and definitely will be back. Our family consisted of 8 people ages 50 to 91! Thanks you! "
Aly B. 4-night trip
Posted 3 days ago
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.

Find out more about Winter

Find out more about Winter

Search for holiday rentals in Winter on Expedia! You can easily find your home rentals, villas, holiday apartments in Winter using one of the methods below:

  • View our selection of featured holiday rentals in Winter
  • Use the map to find apartments and other holiday homes in the Winter neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winter while they last

Look no further and take a look at our great range of rental properties in Winter!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Winter?

Yes, you can find vacation rentals near top attractions in Winter, or you can choose a more secluded option if you're looking for relaxation.

What's the top vacation rental in Winter?

5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.: This Winter vacation home rental is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Winter?

Choose from 12 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Lake Winter and Chequamegon National Forest are a couple of lovely local spots to get outside and enjoy nature. Flambeau River and Ojibwa State Park are other places to visit while you're in town.

What are vacation rentals like in Winter?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Winter. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.