Dudley Vacations from $500

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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.
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
Price was $846, price is now $500 per person
$500
per person
Jan 15 - Jan 18
found 9 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
8.4/10 Very Good! (431 reviews)

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,565, price is now $768 per person
$768
per person
Dec 21 - Dec 26
just found
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,816, price is now $1,707 per person
$1,707
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was $993, price is now $617 per person
$617
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The room was clean but unfortunately they chose to assign me to building 5 which was an ancillary building in the parking lot with no doorman. No help and I struggled through two sets of heavy doors alone. View of parking lot. I paid $350 to stay at a waterfront hotel, if I wanted a parking lot view I could have gotten it at Motel 6.

Reviewed on Nov 3, 2026

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $886, price is now $614 per person
$614
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.2/10 Wonderful! (2,088 reviews)
Room : clean Breakfast: variety of good choice Staff: polite and friendly Parking: plenty of available spots

Reviewed on Nov 4, 2026

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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.
See properties

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
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from Nov 9 to Nov 10
$88 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (1,800 reviews)
"."

Reviewed on Nov 3, 2026

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
$96 nightly
The price is $108 total per night from Nov 22 to Nov 23
$108 total
Nov 22 - Nov 23
Total with taxes and fees
Wellsworth Hotel
Comfort Inn Auburn - Worcester

Comfort Inn Auburn - Worcester

2.5 out of 5
426 Southbridge St Auburn MA
Fully refundable
$84 nightly
The price is $94 total per night from Nov 29 to Nov 30
$94 total
Nov 29 - Nov 30
Total with taxes and fees
Comfort Inn Auburn - Worcester
See all 391 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 $500 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.