Winter Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Winter

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

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

Winter
10.0 out of 10, Exceptional, (68)
"We had a great time at the cabin! We had our whole family there and the kids and adults loved the game room, the screened in porch, fire pit, water trampoline, and all the yard space. Lots of games were played and tons of fun was had by all! Thank you for a great stay!"
United States
Emily B.
5 bedroom 3- bath 8 people capacity pontoon included in Winter Wis.
Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio
Telemark Northwoods Lodging

Telemark Northwoods Lodging

3.5 star property
Cable
9.0 out of 10, Wonderful, (316)
"Great room excellent people to worh with."
United States
Doyle
The price is ￥22,739
￥48,008 total
includes taxes & fees
Nov 27 - Nov 28
Telemark Northwoods Lodging
House (3 Bedrooms) | Interior
A-frame Cabin w/ Private Boat Dock!

A-frame Cabin w/ Private Boat Dock!

3.0 star property
Butternut
A-frame Cabin w/ Private Boat Dock!
Dining
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!

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

Hayward
9.6 out of 10, Exceptional, (210)
"Nice property in a great location. Problem is there was no air conditioning and with the extensive heat at the beginning of our stay and the bad air quality due to the Canadian fires we were not able to enjoy the cabin as we would have liked. We ended up leaving one night early. "
United States
Jim H.
Very Private Cabin on Upper Twin Lake...Great Views...Close to Trails!
Property grounds
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!

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

Hayward
10.0 out of 10, Exceptional, (75)
"Loved our stay for Birkie weekend!"
United States
Christine S.
Hayward, Round Lake Retreat! Private dock, 3 kayaks, beautifully maintained!
Property grounds
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring

LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring

Northwoods Beach
10.0 out of 10, Exceptional, (32)
"We had a wonderful stay in the cabin. It is on a crystal clear lake that we love to that swim in and kayak and paddle boarding!! Our 3rd summer staying here. Zach is an excellent host especially with communication! We’ve already planned another visit next summer."
United States
Stacy Z.
LCO Lakefront Cabin - Discounted for the Fall, Winter, & Spring
Interior
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests

Hayward
9.6 out of 10, Exceptional, (79)
"Great location, lots of room, and cute cabins."
United States
Stephanie C.
Hayward Lakefront - Gorgeous Cabin, Four Seasons of Fun for up to 21 guests
Exterior
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake

Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake

Hayward
10.0 out of 10, Exceptional, (18)
"Wonderful stay - very peaceful. Terrific communication with the host. "
United States
Jason
Big Sisu - Newly Remodeled Nordic Hideaway on Silverthorn Lake
Bar (on property)
Executive Custom Log Lodge on Little Round Lake

Executive Custom Log Lodge on Little Round Lake

Hayward
10.0 out of 10, Exceptional, (102)
"An excellent place for our family. We enjoyed the many areas for our family to play board games, card games and plenty of places for quiet time for our group. The extra fridge space was a luxury for our family meals. Our group enjoyed the outdoor decks and fire pit! Everything was as expected or better. "
United States
Steph L.
Executive Custom Log Lodge on Little Round Lake
Outdoor dining
Modern Cabin located between Grindstone and Lac Courte Oreilles

Modern Cabin located between Grindstone and Lac Courte Oreilles

Northwoods Beach
10.0 out of 10, Exceptional, (76)
"Wonderful and extremely clean cabin! It had everything we needed for a great stay!"
United States
Brian F.
Modern Cabin located between Grindstone and Lac Courte Oreilles
Exterior
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake

2.0 star property
Hayward
10.0 out of 10, Exceptional, (9)
"Simple Checkin, Responsive Host, Nice Location and property equipped to host 20+ person. Stayed 2 memorable and fun nights...."
United States
SANTHOSH KUMAR M.
Charming 5-bedroom cabin just outside Hayward near OO, Tiger Cat,and Spider Lake
Interior
Cozy Cabin on Secluded Peninsula

Cozy Cabin on Secluded Peninsula

Hayward
9.8 out of 10, Exceptional, (48)
"We rented this cabin because we needed a place that would allow our dogs and this was that and so much more. The cabin is set back in the woods so its quiet and secluded, really gives you that upnorth feel. Everything was just as described and would absolutely stay again."
United States
James G.
Cozy Cabin on Secluded Peninsula
Terrace/patio
Lake House & Cottage-2 Docks, Firepits, Kitchens

Lake House & Cottage-2 Docks, Firepits, Kitchens

Hayward
9.8 out of 10, Exceptional, (18)
"We had a wonderful family getaway with our adult children and grandchildren. We all had a cozy place to sleep and great spaces to gather this chilly fall weekend. We would highly recommended this cabin and lake views."
United States
Delores W.
The price is ￥120,660
￥151,018 total
includes taxes & fees
Nov 17 - Nov 18
Lake House & Cottage-2 Docks, Firepits, Kitchens
Smart TV, fireplace, DVD player, books
Breezy Bay Beach On Round Lake

Breezy Bay Beach On Round Lake

Hayward
10.0 out of 10, Exceptional, (61)
"Family of nine thoroughly enjoyed our stay. Great accommodations and beach. Paddle boat was a treat. Great location for fireworks."
United States
Dan W.
Breezy Bay Beach On Round Lake
Outdoor dining
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.

Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.

Hayward
10.0 out of 10, Exceptional, (3)
"Beautiful, beautiful home! Absolutely everything was provided, other than food. Soft water in the house, great TVs and furniture. Very comfortable! Rent the boat or bring your own, as you need to get out on that clean, clear water! Deer came through the yard morning and night, eating up the acorns, otters playing in the water out on the lake. Dave had the firepit ready to go for us, as well as the sauna tent. It's located on a back bay, so nice and quiet. Close to town, but not too...
United States
Diane H.
Northwoods Hayward Haven. Private 3 bedroom 3 bath, sleeps 8 very comfortably.
Smart TV, fireplace, DVD player
Rustic and Charming one Bedroom cabin. Upgraded pontoon!

Rustic and Charming one Bedroom cabin. Upgraded pontoon!

Hayward
9.8 out of 10, Exceptional, (97)
"This was our 3rd stay! We love it. "
United States
Paulina L.
Rustic and Charming one Bedroom cabin. Upgraded pontoon!
Interior
Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

Sandalwood Retreat on Round Lake - Waterfront property with screened porch 

Hayward
10.0 out of 10, Exceptional, (41)
"We used to own a home in this area, and our grown children wanted to revisit the area with their families. This property was perfect for the 10 of us. The property provided all the necessary features to provide fun on a rainy day, along with the outdoor activities later in the week. We would definitely recommend this property and will look forward to returning in the future. "
United States
Margie Z.
Sandalwood Retreat on Round Lake - Waterfront property with screened porch 
Smart TV, fireplace
Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles

Northwoods Beach
10.0 out of 10, Exceptional, (18)
"Brandon was great and place was exactly as advertised. "
United States
Richard C.
Charming 2-bedroom Hayward Cabin on Lac Courte Oreilles
Terrace/patio
Moose Lake Hayward WI

Moose Lake Hayward WI

2.0 star property
Hayward
10.0 out of 10, Exceptional, (11)
"Our first time staying here. Perfect cabin for our weekend of fishing. Wish we had booked a couple more days. Walleye fishing was excellent. We will be back."
United States
Tony S
Moose Lake Hayward WI
Exterior
1940’s Charming Vintage Cabin

1940’s Charming Vintage Cabin

Northwoods Beach
10.0 out of 10, Exceptional, (8)
"Did some river kayaking in the area. Perfect place to stay."
United States
Daniel F.
1940’s Charming Vintage Cabin
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Hotel Reviews

Holiday Inn Express & Suites Hayward by IHG

Holiday Inn Express & Suites Hayward by IHG

10/10 Excellent
"The staff is extremely friendly and efficient. Amanda at the Front Desk and attendant at breakfast on 11/11 were great!"
Patrick 2-night trip
Posted 1 day ago
Holiday Inn Express & Suites Hayward by IHG

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!

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.