Dudley Vacations from $382

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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.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $532, price is now $382 per person
$382
per person
Mar 27 - Mar 31
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Nice place. Clean and comfortable bed. Nice shower. Only issue was the heating/air system was a older wall mounted split which was very loud and in sorely in need of maintenance. Hard to get to sleep and it kept waking me up ss it turned on and off. The check in person, Franklin, was very nice and efficient.

Reviewed on Jan 29, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,441, price is now $960 per person
$960
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $880, price is now $592 per person
$592
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,891 reviews)
Spotless and perfect balcony

Reviewed on Jan 31, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $882, price is now $595 per person
$595
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Thank you for the cool corner suite on the 9th floor! We stayed over after attending a Bruins game. Short stay but nice place. Good location for our adventures. We’ll stay again if when we are back in Boston! Ty

Reviewed on Jan 29, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was $634, price is now $451 per person
$451
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

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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

Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Feb 2 to Feb 3
$113 total
Feb 2 - Feb 3
Total with taxes and fees
9/10 Wonderful! (1,404 reviews)
Great place

Reviewed on Jan 28, 2026

Wellsworth Hotel
Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

3 out of 5
35 Major Taylor Boulevard Worcester MA
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $145 total per night from Feb 10 to Feb 11
$145 total
Feb 10 - Feb 11
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
Clean spacious room, pool was clean, food was good. Quiet rooms. I could actually sleep during a cheer competition.

Reviewed on Jan 25, 2026

Hilton Garden Inn Worcester
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
$151 nightly
The price is $173 total per night from Feb 15 to Feb 16
$173 total
Feb 15 - Feb 16
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Clean, spacious rooms, nice restaurant next door. Good customer service

Reviewed on Jan 25, 2026

AC Hotel by Marriott Worcester
See all 349 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.

Find the Best Dudley Vacation Packages

Dudley Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
11,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Breezy Picnic Grounds & Waterslides, Wells State Park and TriState Speedway

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Frequently asked questions

How much does a Dudley vacation package cost?
You'll find cheap prices from $382 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.

Explore a world of travel with Expedia

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