Dorchester Vacations from $320
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Your Dorchester Vacation
When a city escape is calling your name, answer it with a vacation package to Dorchester. With all your travel needs worked out before you go, all you have to do here is concentrate on having a ball. Wondering what you should see or do first during your trip to Dorchester? Head for well-known attractions such as Dorchester Park. Whatever your travel plans or the size of your budget, organizing a tailored Dorchester vacation is easy with Expedia.
The Latest Dorchester vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Flamingo Bay Resort
Spring Valley
Save 100% on your flight
Price was $689, price is now $320 per person
$320
per person
Aug 5 - Aug 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Las Vegas (LAS)
8.8/10 Excellent! (1,001 reviews)
This was a cool place to stay. I like the gated community feel with security upon entry. There's Smiths for groceries less than a quarter mile away and plenty of places for shopping. Staff is good. The only thing I'd say about is that TVs you can only watch local channels ( no Netflix access or any other app).Full kitchen, washer, and dryer in unit.
Reviewed on Jun 3, 2026
Casablanca Miami Beach
North Beach
Price was $5,979, price is now $2,554 per person
$2,554
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
The Yellow Penthouse
Price was $2,810, price is now $1,338 per person
$1,338
per person
Aug 6 - Aug 12
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
6.2/10 (181 reviews)
Muy tranquilo y muy buena onda el muchacho que atiende
Reviewed on May 17, 2026
Dorchester Hotel Deals
Rodeway Inn Abbotsford
300 East Elderberry Road Colby WI
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $94 total per night from Jun 7 to Jun 8
$94 total
Jun 7 - Jun 8
Total with taxes and fees
7.4/10 Good! (323 reviews)
"Undergoing renovations and the contractor and hotel have the place looking like a complete mess. Crap all over the place. Extremely loud all night with a lot of inconsiderate guests and no staff anywhere."
Reviewed on May 24, 2026
FairBridge Inn & Suites in Thorp, WI
203 West Hill St Thorp WI
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $152 total per night from Jun 14 to Jun 15
$152 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (330 reviews)
"Breakfast was empty first time I came out. 2nd time was there but was cold. Need bigger and better stuff for breakfast. Room was clean."
Reviewed on May 6, 2026
Woodlands Inn & Suites
854 N. 8th Street Medford WI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $99 total per night from Jun 7 to Jun 8
$99 total
Jun 7 - Jun 8
Total with taxes and fees
7.8/10 Good! (337 reviews)
"It was a cute hotel. My only prom was the mattress needs to be replaced they’re pretty worn out."
Reviewed on May 31, 2026
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 |
Population | 860 |
Max Temp Winter | 20ºF |
Max Temp Summer | 75ºF |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.