Dudley Vacations from $231

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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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $404, price is now $231 per person
$231
per person
Feb 26 - Mar 1
found 10 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Nice room with separate living room. We enjoyed the gym, pool and hot tub. We stayed on second floor and there is only one elevator, so you have to wait sometime. I wish there is stairs to walk down.

Reviewed on Jan 6, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,474, price is now $823 per person
$823
per person
Mar 13 - Mar 18
found 10 hours ago
Roundtrip flight included
Dallas (DFW) 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

citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was $823, price is now $476 per person
$476
per person
Feb 13 - Feb 20
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (2,013 reviews)
Really sharp, modern looking room. Excellent sound isolation from street noise. Bathroom isn't super private.

Reviewed on Jan 7, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $831, price is now $484 per person
$484
per person
Mar 20 - Mar 23
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Such a warm and cozy place with great amenities!

Reviewed on Dec 31, 2025

Ashworth by the Sea

Ashworth by the Sea

3 out of 5
Hampton Beach
Save 100% on your flight
Price was $421, price is now $283 per person
$283
per person
Mar 17 - Mar 21
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.2/10 Very Good! (1,319 reviews)
Clean and comfortable

Reviewed on Jan 4, 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

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
$118 nightly
The price is $135 total per night from Jan 12 to Jan 13
$135 total
Jan 12 - Jan 13
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Staff

Reviewed on Jan 4, 2026

Hilton Garden Inn Worcester
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
$89 nightly
The price is $99 total per night from Jan 9 to Jan 10
$99 total
Jan 9 - Jan 10
Total with taxes and fees
9/10 Wonderful! (1,599 reviews)
This was a quick overnight visit. the room was clean and warm. The continental breakfast was tasty and the coffee was good. The staff were pleasant.

Reviewed on Jan 6, 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
$101 nightly
The price is $113 total per night from Jan 11 to Jan 12
$113 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,389 reviews)
Very clean room

Reviewed on Jan 4, 2026

Wellsworth Hotel
See all 351 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 $231 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.