Dudley Vacations from $179

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Your Dudley Vacation

Cuisine, art, entertainment and more … There's a whole lot to discover with a Dudley vacation package. And with the ability to customize your city adventure, it's guaranteed to be one that's tough to forget. Indian Ranch, Lake Chaubunagungamaug and Lake Webster are just some of the many attractions you'll want to explore during your trip to Dudley. Whoever you're escaping with and whatever your bank balance, your ultimate Dudley vacation is just a few clicks away with Expedia.

The Latest Dudley vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
Price was $292, price is now $179 per person
$179
per person
Oct 23 - Oct 26
just found
Roundtrip flight included
Miami (MIA) to Boston (BOS)
7.8/10 Good! (779 reviews)
We stayed in the Annex which is the old section. The floor in our room was absolutely filthy. Threw away socks and put shoes on whenever we had to walk around. Non smoking but could smell smoke in the room from other guests. Air conditioner was very loud as unit was old. However, bed was very comfortable. Would I stay here again? Not too sure!

Reviewed on Aug 22, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $650, price is now $329 per person
$329
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $698, price is now $430 per person
$430
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.2/10 Very Good! (1,007 reviews)
people and property where great the bathroom was spotless but needs upgrade

Reviewed on Aug 23, 2025

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $514, price is now $317 per person
$317
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,226 reviews)
Consistently excellent stay

Reviewed on Aug 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
Price was $387, price is now $245 per person
$245
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great location, very comfortable beds. The lighting in the room could be better.

Reviewed on Aug 14, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Dudley

TriState Speedway

Take the family on an outing to TriState Speedway during your trip to Dudley. While in this quaint area, you can savor the top-notch restaurants.

TriState Speedway

Dudley Hotel Deals

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
$99 nightly
The price is $111 total per night from Aug 24 to Aug 25
$111 total
Aug 24 - Aug 25
Total with taxes and fees
8.8/10 Excellent! (1,471 reviews)
A great place to stay and visit history, too!
"This historic Inn is a visit into history. There are original room available, but plenty of modern ones, too. The grounds are well maintained. The staff is very friendly and just waiting to help you. Do not overlook the bakery! Old and new recipes right there. The food is excellent."

Reviewed on Aug 21, 2025

Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $140 total per night from Aug 25 to Aug 26
$140 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (1,274 reviews)
"Consistently excellent stay and value"

Reviewed on Aug 22, 2025

Wellsworth Hotel
AC Hotel by Marriott Worcester

AC Hotel by Marriott Worcester

3.5 out of 5
125 Front St, Worcester, MA
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $205 total per night from Aug 31 to Sep 1
$205 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"very new, clean and updated. very upper class feel as far as design and staff..we had excellent experience with all."

Reviewed on Aug 14, 2025

AC Hotel by Marriott Worcester
See all 316 properties in Dudley
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.

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Frequently asked questions

How much does a Dudley vacation package cost?
You'll find cheap prices from $179 on Expedia for your Dudley break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Dudley costs.
What are the cheapest months to go to Dudley?
If you're looking to score a cheap Dudley vacation package, consider visiting in December, January and February. You'll usually find lower rates on hotels and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Dudley?
Generally, a handful of days is enough to check out the main attractions during your Dudley vacation. However, if you prefer to have more time to chill out or take day trips, consider extending your trip.
How to find the best Dudley package deals?
Bagging a cheap Dudley package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Dudley package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Dudley vacation as a package?
You can enjoy significant savings on your Dudley break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Dudley?
If you've got your Dudley vacation dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Dudley vacation packages?
Secure your ideal getaway to Dudley with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until your next payday — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stay on budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.