Dudley Vacations from $696

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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.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $984, price is now $696 per person
$696
per person
Apr 5 - Apr 10
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (4,672 reviews)
Friendly staff, clean room, good location.

Reviewed on Jan 27, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,341, price is now $884 per person
$884
per person
Apr 5 - Apr 10
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
The staff was fantastic!

Reviewed on Jan 24, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $2,458, price is now $1,672 per person
$1,672
per person
Apr 16 - Apr 22
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,206, price is now $825 per person
$825
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
beautiful, clean rooms, well appointed

Reviewed on Jan 23, 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 Jan 29 to Jan 30
$113 total
Jan 29 - Jan 30
Total with taxes and fees
9/10 Wonderful! (1,398 reviews)
Great hotel for the money. No complaints.

Reviewed on Jan 24, 2026

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
$159 nightly
The price is $182 total per night from Jan 29 to Jan 30
$182 total
Jan 29 - Jan 30
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Brand new / excellent

Reviewed on Jan 19, 2026

AC Hotel by Marriott Worcester
Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St Auburn MA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $94 total per night from Jan 31 to Feb 1
$94 total
Jan 31 - Feb 1
Total with taxes and fees
7.6/10 Good! (1,023 reviews)
Yes

Reviewed on Jan 18, 2026

Comfort Inn Auburn - Worcester
See all 352 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 $696 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.

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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.