Dorchester Vacation Packages

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Top Dorchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Edge Of The Woods Motel

Edge Of The Woods Motel

2 out of 5
per person
Sep 3 - Sep 9
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to La Crosse (LSE)
8.8/10 Excellent! (64 reviews)
staff was very nice and accommodating. hotel room was nice, clean, and spacious.

Reviewed on Jul. 14, 2025

Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
per person
Sep 3 - Sep 9
found 1 hour ago
Roundtrip non-stop flight included
Winnipeg (YWG) to La Crosse (LSE)
8.2/10 Very Good! (721 reviews)
Just off interstate with parking out front.

Reviewed on Jul. 12, 2025

Ready to book your vacation to Dorchester?

 

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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
The price is CA $185 per night from Jul 20 to Jul 21
CA $185
CA $491 total
Jul 20 - Jul 21
includes taxes & fees
Hunters Hollow Lodge W/ Outdoor Hot Tub & New Swimming Pool
Lazy River Cabin
Lazy River Cabin
Dorchester
The price is CA $256 per night from Aug 3 to Aug 4
CA $256
CA $477 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (48 reviews)
Great property!
"10/10 recommend this house, great space. Very clean. Good parking."

Reviewed on Jun. 22, 2025

Lazy River Cabin
Tiny House on Upper Iowa River w/ hot tub
Tiny House on Upper Iowa River w/ hot tub
dorchester
The price is CA $171 per night from Aug 5 to Aug 6
CA $171
CA $328 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (36 reviews)
Wonderful stay on the Upper Iowa River!
"This was the perfect little house for me and my partner to stay at while we fished the driftless area. The tiny is house is adorable and functional. It was clean and had way more amenities than expected - tons of towels, bedding, extra toilet paper, fully stocked kitchen utensils. There is a ton ..."

Reviewed on Jun. 7, 2025

Tiny House on Upper Iowa River w/ hot tub
See all 227 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Dorchester vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,016 on Expedia. But how much your vacation to Dorchester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Dorchester?
To pick up cheap Dorchester vacation packages, plan your trip outside of busy periods like public holidays and major festivals. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Dorchester?
With a well-organized itinerary, you can easily hit the main Dorchester sights in a handful of days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Dorchester vacation for longer.
How to find the best Dorchester package deals?
Use Expedia's filters to help you find some tempting Dorchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Dorchester package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Dorchester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays separately. Better still, you can customize your Dorchester escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Dorchester?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Dorchester break.
How to plan a trip to Dorchester?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Dorchester.
  2. Plan your budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Dorchester.
  3. Set the duration of your trip: Start by listing all the attractions you want to get to in Dorchester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Dorchester vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.