Dorchester Vacations from $1,034

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Dorchester 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 $1,164, price is now $1,034 per person
$1,034
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to La Crosse (LSE)
9.4/10 Exceptional! (1,003 reviews)
Clean and comfortable

Reviewed on Nov 12, 2025

Hatchery Riverside Hotel & Event Venue

Hatchery Riverside Hotel & Event Venue

3 out of 5
Historic Downtown La Crosse
Price was $1,278, price is now $1,102 per person
$1,102
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to La Crosse (LSE)
10/10 Exceptional! (72 reviews)
Very unique property, comfortable and cozy, very personable experience

Reviewed on Oct 15, 2025

Hampton Inn Lacrosse/Onalaska

Hampton Inn Lacrosse/Onalaska

2.5 out of 5
Price was $1,307, price is now $1,172 per person
$1,172
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to La Crosse (LSE)
9/10 Wonderful! (741 reviews)
The staff were very friendly; the place was clean and had a good variety of breakfast items.

Reviewed on Oct 27, 2025

Home2 Suites by Hilton La Crosse

Home2 Suites by Hilton La Crosse

3 out of 5
Historic Downtown La Crosse
Price was $1,218, price is now $1,124 per person
$1,124
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to La Crosse (LSE)
9.4/10 Exceptional! (807 reviews)
Breakfast was great choices

Reviewed on Nov 2, 2025

Hampton Inn & Suites La Crosse Downtown

Hampton Inn & Suites La Crosse Downtown

2.5 out of 5
Historic Downtown La Crosse
Price was $1,171, price is now $1,087 per person
$1,087
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to La Crosse (LSE)
9.6/10 Exceptional! (1,003 reviews)
The breakfast had everything you could imagine including mini scones!

Reviewed on Nov 7, 2025

Don't see what you're looking for?
See all available trips from Columbus to Dorchester
View all trips

Dorchester Hotel Deals

Tiny House on Upper Iowa River w/ hot tub

Tiny House on Upper Iowa River w/ hot tub

dorchester
$204 nightly
The price is $228 total per night from Nov 16 to Nov 17
$228 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (41 reviews)
Great place. Loved sitting in hot tub watching the river at sunset.

Reviewed on Sep 4, 2025

Tiny House on Upper Iowa River w/ hot tub
Sportsmen Motel

Sportsmen Motel

2 out of 5
2753 Iowa 76, Dorchester, IA
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $102 total per night from Nov 15 to Nov 16
$102 total
Nov 15 - Nov 16
Total with taxes and fees
8.8/10 Excellent! (46 reviews)
Love this place it’s nice and quiet

Reviewed on Nov 10, 2025

Sportsmen Motel
Lazy River Cabin

Lazy River Cabin

Dorchester
$216 nightly
The price is $241 total per night from Nov 16 to Nov 17
$241 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (50 reviews)
Cabin was very clean and had everything you needed for a vacation or getaway

Reviewed on Sep 5, 2025

Lazy River Cabin
See all 235 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)

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Dorchester vacation package cost?
You'll find cheap prices from $1,034 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.