Dorchester Vacations from $675

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The Latest Dorchester vacation packages

Price found within the past 48 hours. Click for updated prices.
AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

3 out of 5
Northside
Price was $752, price is now $675 per person
$675
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
7.6/10 Good! (1,004 reviews)
Seems more run down than it used to be.

Reviewed on May 10, 2026

Hatchery Riverside Hotel & Event Venue

Hatchery Riverside Hotel & Event Venue

3 out of 5
Historic Downtown La Crosse
Price was $1,407, price is now $1,089 per person
$1,089
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
10/10 Exceptional! (92 reviews)
The Hatchery was such a great stay!! Adorable boutique hotel with stylish decor, comfortable amenities, and an overall amazing place. Super easy check in, extra perks like a Victrola in the room with vibing records paired with it, free snacks in the common area (coffee, scones, bags of chips, sodas, etc), great water pressure, and many more!!

Reviewed on Mar 8, 2026

Pearl Street Hotel & Suites

Pearl Street Hotel & Suites

2.5 out of 5
Historic Downtown La Crosse
Price was $1,346, price is now $1,182 per person
$1,182
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
8/10 Very Good! (474 reviews)
Clean and comfortable rooms

Reviewed on May 24, 2026

The Charmant Hotel

The Charmant Hotel

4 out of 5
Historic Downtown La Crosse
Price was $1,001, price is now $886 per person
$886
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
9.8/10 Exceptional! (1,004 reviews)
Everything about this property was top notch. From the hotel room to the restaurant and bar. And fabulous location!

Reviewed on May 25, 2026

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
Price was $780, price is now $711 per person
$711
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
9/10 Wonderful! (1,556 reviews)
We arrived to a surprise free upgrade to a king bedroom with whirlpool tub in the room! Free breakfast each morning was delicious and had a great variety -pancales, eggs, potatoes, cereal, pastries, breads, coffee, juice etc. The pool and HUGE hot tub were beautiful! The giant desktop bell is super fun! The property is very well maintained, clean and has a woodsy, rustic feel!

Reviewed on May 28, 2026

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Dorchester Hotel Deals

Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool

Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool

Dorchester IA
$559 nightly
The price is $626 total per night from Jun 21 to Jun 22
$626 total
Jun 21 - Jun 22
Total with taxes and fees
Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool
Sportsmen Motel

Sportsmen Motel

2 out of 5
2753 Iowa 76 Dorchester IA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Jun 10 to Jun 11
$94 total
Jun 10 - Jun 11
Total with taxes and fees
9/10 Wonderful! (54 reviews)
"It’s a nice, clean, comfortable room, with good wifi and simple amenities that are well maintained. Just make sure you have WiFi calling enabled because you will not have service and you need to call to get into your room. (Not the motel’s fault at all, the online bookings don’t give them any ..."

Reviewed on May 6, 2026

Sportsmen Motel
Lazy River Cabin

Lazy River Cabin

Dorchester IA
$216 nightly
The price is $241 total per night from May 31 to Jun 1
$241 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (60 reviews)
"We stayed during the off season, spending our spring break exploring the driftless area. House was warm & welcoming and we enjoyed the hot tub. Very hands off communication with the host. We had everything we needed. Roadway was busy but the noise didn’t bother us. Fun spot!"

Reviewed on Apr 2, 2026

Lazy River Cabin
See all 237 properties in Dorchester
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 Dorchester Vacation Packages

Dorchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
La Crosse Municipal Airport (LSE)

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Frequently asked questions

How much does a Dorchester vacation package cost?
You'll find cheap prices from $675 on Expedia for your Dorchester getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Dorchester costs.
What are the cheapest months to go to Dorchester?
If you'd like to score a cheap Dorchester vacation package, consider planning a trip in June, November and December. You're likely to find better rates on hotels and airfares during these months — perfect for budget-conscious travelers.
How many days is enough for Dorchester?
The ideal length of your Dorchester vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Dorchester package deals?
Landing a cheap Dorchester package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Dorchester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Dorchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Dorchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Dorchester?
Secure incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Dorchester getaway.
Does Expedia offer Book Now, Pay Later Dorchester vacation packages?
If you're like us, you love traveling but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Dorchester vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap 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.