Dudley Vacations from $571
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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.
Arcadian Hotel
Coolidge Corner
$571
per person
Dec 13 - Dec 18
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.2/10 Very Good! (4,438 reviews)
While we enjoyed our stay for that one night, we will put in a room that did not have any windows which I don't think it's safe... honestly we were too tired to worry about it so just spend the night and check out the next day. The room was clean.
Although they provide in room coffee, there were no cups to put the coffee in.
Reviewed on Sep 19, 2026
Boston Lodge and Suites
Dorchester
$1,455
per person
Dec 4 - Dec 7
found 16 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
$1,020
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.6/10 Exceptional! (265 reviews)
I had a King room with a fireplace, it was a nice size room and very clean. The bathroom was nice and they had a robe hanging for me. Little touches like personalized notes and soft drinks in the refrigerator and snacks to pick up for the room. The staff was very friendly. I'm not a breakfast eater so can't really comment on that although there was a nice continental spread and you could order off the menu. I will say that I was a bit disappointed in the restaurant. Had dinner there the night before and for the price, I felt the food was a little lackluster. The bartender was very nice and he was my server as well. All in all I really enjoyed my stay and if I go back to Lexington I would stay there again.
Reviewed on Sep 4, 2026
Stay near popular Dudley attractions
Nichols College
This business-focused private college in Dudley, Massachusetts offers a distinctive AACSB-accredited curriculum centered on leadership development. Explore the 220-acre campus with its classic New England architecture.
Dudley Hill Golf Club at Nichols College
This historic 9-hole course from 1926 challenges golfers with its small greens and wide fairways. Enjoy a round followed by refreshments at the "Bison Den" clubhouse with its welcoming restaurant and bar.
Conant Library
Conant Library at Nichols College offers extensive academic resources in a serene study environment. Access research materials, computers, and expert help during less crowded weekday mornings.
Stevens Park
After visiting Stevens Park, make a plan to see the other sights and activities in Dudley.
Berthol Field
Berthol Field offers a quiet retreat from the tourist crowds, frequented mainly by locals. Enjoy the authentic neighborhood atmosphere while watching community sports or events.
Slater Woods
Slater Woods offers 200 acres of protected wilderness with pristine Peter Pond shoreline. Hike the peaceful 2.5-mile trail through diverse habitats while spotting local wildlife in this tranquil Massachusetts retreat.
Tufts Branch Valley Wildlife Sanctuary
This tranquil sanctuary features a loop trail through meadows and woodlands ideal for wildlife observation. Morning visits offer cooler temperatures and more animal activity along well-maintained paths.
Hiland Park
Hiland Park's 52.8 acres of woodland trails offer a serene escape for nature lovers in Dudley, Massachusetts. Perfect for birdwatching, photography, and peaceful walks through changing seasonal beauty.
Dudley Hotel Deals
Wellsworth Hotel
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
$125 nightly
$140 total
Oct 4 - Oct 5
Total with taxes and fees
La Quinta Inn by Wyndham Auburn Worcester
446 Southbridge St Auburn MA
Fully refundableReserve now, pay when you stay
$89 nightly
$99 total
Sep 28 - Sep 29
Total with taxes and fees
Comfort Inn Auburn - Worcester
426 Southbridge St Auburn MA
Fully refundable
$84 nightly
$94 total
Oct 18 - Oct 19
Total with taxes and fees
8/10 Very Good! (1,264 reviews)
"Excellent"
Reviewed on Sep 19, 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 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 $571 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
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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.
