Winter Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Winter vacation rentals

Deluxe Suite, 1 Bedroom, Kitchen | Terrace/patio

Telemark Northwoods Lodging

Telemark Northwoods Lodging
3.5 star property
Cable
9.0 out of 10, Wonderful, (318 reviews)
"Beautiful setting, relaxing stay, comfortable and clean accommodations, super nice staff."
United States
Sarah
$307 nightly
The price is $336
Jun 16 - Jun 17
Total with taxes and fees
Telemark Northwoods Lodging
House (4 Bedrooms) | Interior

Northwoods Escape: Lakeside Retreat w/ Deck

Northwoods Escape: Lakeside Retreat w/ Deck
3.0 star property
Stone Lake
$578 nightly
The price is $608
Jun 7 - Jun 8
Total with taxes and fees
Northwoods Escape: Lakeside Retreat w/ Deck
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

AmericInn by Wyndham Ladysmith

AmericInn by Wyndham Ladysmith

2/10 Terrible
"If possible I would give this hotel 0 stars but I have to give it 1 star. I booked this hotel through Expedia and got trip insurance just in case my family visiting from across the world had a delay. When I attempted to call to cancel or change my stay, a freshly graduated 18 year old from the school I teach at said she was unable to do anything on her end to help, didn’t have a manager answering, and didn’t have advice for me. (I don’t blame the child as I know she is smart, she clearly had poor supervisors). When I got the key to my room, I entered and immediately was hit in the face with the smell of water damage and mold. When I went to inform the front desk the same girl said they were booked out. I have a severe allergy to mold, and needed to take my inhaler from 2 minutes in the dirty room. I asked for a manager to call me as I would not be staying there and wanted a refund for the room. I never got a call back, and my family paid almost $400 plus the cost of another hotel 20 miles away because of the mold."
Kayla 2-night trip
Posted 13 hours ago
AmericInn by Wyndham Ladysmith

Find out more about Winter

Everything you need to know about Winter vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winter vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winter vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winter vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winter. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winter in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $299 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winter rentals

At Expedia, we put the best Winter vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winter rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winter vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winter. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Bears Den on the private lake: This Winter vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Winter?

Choose from 11 Expedia vacation rentals in Winter for a memorable vacation.

What can I see and do in Winter?

Perch Lake and Barker Lake are a couple of lovely local spots to get outside and enjoy nature. Bluegill Lake and Fishtrap Lake 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.