Westby Vacations from $963

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Your Westby Vacation

Our Westby vacation packages give you endless opportunities to discover new sights, sounds and flavors. And with all the details worked out, you can relax and enjoy your city break without a care in the world. Any trip to Westby needs a well-thought-out itinerary. Fill yours with major attractions such as Branches Winery, Snowflake Ski & Golf Club and Dregnes Scandinavian Gifts. Whoever you're heading away with and whatever you plan to spend, your ultimate Westby vacation is just clicks away with Expedia.

The Latest Westby vacation packages

Price found within the past 48 hours. Click for updated prices.
Gundersen Hotel & Suites

Gundersen Hotel & Suites

2.5 out of 5
Powell-Poage-Hamilton
Price was $1,135, price is now $963 per person
$963
per person
Jan 16 - Jan 19
found 11 hours ago
Roundtrip flight included
Billings (BIL) to La Crosse (LSE)
9.4/10 Exceptional! (1,003 reviews)
Room was very clean. Staff was friendly.

Reviewed on Dec 8, 2025

The Charmant Hotel

The Charmant Hotel

4 out of 5
Historic Downtown La Crosse
Price was $1,195, price is now $1,065 per person
$1,065
per person
Jan 16 - Jan 19
found 11 hours ago
Roundtrip flight included
Billings (BIL) to La Crosse (LSE)
9.6/10 Exceptional! (1,002 reviews)
Great staff, wonderful room

Reviewed on Dec 16, 2025

GrandStay Hotel & Suites

GrandStay Hotel & Suites

2.5 out of 5
Historic Downtown La Crosse
Price was $1,130, price is now $1,012 per person
$1,012
per person
Jan 16 - Jan 19
found 11 hours ago
Roundtrip flight included
Billings (BIL) to La Crosse (LSE)
9/10 Wonderful! (1,028 reviews)
Great location & nice large suite

Reviewed on Dec 15, 2025

Country Inn & Suites by Radisson, Sparta, WI

Country Inn & Suites by Radisson, Sparta, WI

2.5 out of 5
Price was $1,105, price is now $991 per person
$991
per person
Jan 16 - Jan 19
found 11 hours ago
Roundtrip flight included
Billings (BIL) to La Crosse (LSE)
7.6/10 Good! (225 reviews)
Last time I stayed there it was great this time. It was still good, but I wanted to use the fridge and then get very cold. The water took forever to heat up for the shower, but that also might be because it was colder outside.

Reviewed on Nov 20, 2025

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
Price was $1,126, price is now $1,013 per person
$1,013
per person
Jan 16 - Jan 19
found 11 hours ago
Roundtrip flight included
Billings (BIL) to La Crosse (LSE)
9/10 Wonderful! (1,577 reviews)
Always enjoy staying at Stoney Creek when visiting the La Crosse area!

Reviewed on Dec 16, 2025

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Discover the most popular places to visit in Westby

Branches Winery

4.5/5(3 reviews)

You can enjoy a tasting or tour at Branches Winery during your travels to Westby. Wander around the forests in this relaxing area, or simply enjoy its restaurants.

Branches Winery

Snowflake Ski & Golf Club

Enjoy a round of golf in Westby at Snowflake Ski & Golf Club. You can enjoy the restaurants while in the area.

Snowflake Ski & Golf Club

Dregne's Scandinavian Gifts

3/5(1 review)

Take the family on an outing to Dregne's Scandinavian Gifts during your trip to Westby. Wander around the forests in this relaxing area, or simply enjoy its restaurants.

Dregne's Scandinavian Gifts

Westby Hotel Deals

Old Towne Motel

Old Towne Motel

2 out of 5
Hwy. 14, 61 & 27 South Westby WI
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $73 total per night from Dec 18 to Dec 19
$73 total
Dec 18 - Dec 19
Total with taxes and fees
7.8/10 Good! (241 reviews)
Clean and spacious

Reviewed on Dec 12, 2025

Old Towne Motel
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.

Westby WI
9.8/10 Exceptional! (14 reviews)
Clean - nice amenities-

Reviewed on Nov 27, 2025

Get rates
Westby Hideaway: Charming & Cozy 2-Bedroom Cabin on a Peaceful Dead-End Road.
Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
3060 S Kinney Coulee Rd Onalaska WI
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $112 total per night from Dec 24 to Dec 25
$112 total
Dec 24 - Dec 25
Total with taxes and fees
8.8/10 Excellent! (1,587 reviews)
Nice, clean, good breakfast

Reviewed on Dec 9, 2025

Stoney Creek Hotel La Crosse - Onalaska
See all 427 properties in Westby
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.

Find the Best Westby Vacation Packages

Westby Essential Information

Language
English
Currency
U.S dollars
Closest Airport
La Crosse Municipal Airport (LSE)
Population
2,300
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Vernon Vineyards, Branches Winery and Fortney Underground Theater

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Frequently asked questions

How much does a Westby vacation package cost?
You'll find cheap prices from $963 on Expedia for your Westby break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Westby costs.
What are the cheapest months to go to Westby?
November, December and January are the best times to search for cheap Westby vacation packages. Traveling in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Westby?
With a well-organized travel plan, you can easily tick off the top Westby sights in a few days. But if you want to discover hidden gems or take day trips, consider booking your Westby vacation for longer.
How to find the best Westby package deals?
Start your search for a Westby package deal by entering your destination and travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Westby package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Westby escape off to a flying start.
Is it cheaper to book a Westby vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking hotels and flights individually. Better still, you can tailor your Westby getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Westby?
If you have your Westby vacation dates locked in, book early to grab some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Westby vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Westby trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.