Dudley Vacations from $439

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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 Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $690, price is now $439 per person
$439
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (1,170 reviews)
Free parking, beautiful property, cafe on site and friendly staff

Reviewed on Jul 12, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,933, price is now $1,075 per person
$1,075
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,028, price is now $1,146 per person
$1,146
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (722 reviews)
The staff and amenities at The Nantucket Inn were excellent. In particular, we give a 'shout out' to Balford, who went the extra mile (more than once!) to ensure that my physically challenged husband was accommodated in the best possible and most comfortable way during our transportation to/from town, and to Lisa at the front desk, who was responsive and speedy to our every request for information. Convenient access to the airport (walking-distance) was a bonus, as was the availability of delicious breakfast options (for a cost) and evening cocktails. The kiddoes enjoyed both pools. We would choose to stay here again.

Reviewed on Jul 11, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,286, price is now $795 per person
$795
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $994, price is now $630 per person
$630
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (195 reviews)
The location couldn’t have been more perfect and despite it being a holiday weekend the parking lot/BNB never felt crowded. Everyone we encountered was lovely and helpful, and the room was a perfect place to take a midday nap or unwind after hours on the beach! We would definitely stay again.

Reviewed on Jul 6, 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
$80 nightly
The price is $89 total per night from Aug 12 to Aug 13
$89 total
Aug 12 - Aug 13
Total with taxes and fees
9/10 Wonderful! (1,731 reviews)
"Staff was very friendly and helpful"

Reviewed on Jul 12, 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
$113 nightly
The price is $126 total per night from Jul 27 to Jul 28
$126 total
Jul 27 - Jul 28
Total with taxes and fees
9.2/10 Wonderful! (1,596 reviews)
"Beautiful property but the air conditioning wasn’t working properly. The food at the restaurant was delicious. The pool area was extremely hot and strong smell of chlorine so we were unable to use the pool."

Reviewed on Jul 11, 2026

Wellsworth Hotel
La Quinta Inn by Wyndham Auburn Worcester

La Quinta Inn by Wyndham Auburn Worcester

3 out of 5
446 Southbridge St Auburn MA
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $83 total per night from Jul 26 to Jul 27
$83 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (7 reviews)
"Bright light outside windows at night shone through top of windows, no total darkness at night."

Reviewed on Jul 9, 2026

La Quinta Inn by Wyndham Auburn Worcester
See all 361 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 $439 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.