Dudley Vacations from $283

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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
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (2,262 reviews)
Nice hotel with mediocre breakfast

Reviewed on Aug 1, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Save 100% on your flight
per person
Oct 17 - Oct 22
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (301 reviews)
We love this lodge, it has been our go to for years when we visit Cape Cod.

Reviewed on Aug 2, 2025

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
Downtown Manchester
Save 100% on your flight
per person
Oct 17 - Oct 22
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,000 reviews)
Although I was only there for 1 night I I availed myself of the snack/drinks area in the lobby & the bar. Staff were knowledgeable & friendly. I will definitely go again.

Reviewed on Jul 30, 2025

Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
per person
Oct 17 - Oct 22
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
7.6/10 Good! (393 reviews)
Just a great place to stay at Sun Bird resort inn

Reviewed on Aug 2, 2025

Don't see what you're looking for?
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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

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
$99 nightly
The price is $111 total per night from Aug 3 to Aug 4
$111 total
Aug 3 - Aug 4
Total includes taxes and fees
8.8/10 Excellent! (1,455 reviews)
"Very dog friendly"

Reviewed on Jul 30, 2025

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
$119 nightly
The price is $133 total per night from Aug 3 to Aug 4
$133 total
Aug 3 - Aug 4
Total includes taxes and fees
9/10 Wonderful! (1,256 reviews)
"Clean facility, very spacious"

Reviewed on Aug 1, 2025

Wellsworth Hotel
Holiday Inn Express Hotel & Suites Auburn by IHG

Holiday Inn Express Hotel & Suites Auburn by IHG

2.5 out of 5
10-12 Johnson St, Auburn, MA
Fully refundable
$121 nightly
The price is $135 total per night from Aug 10 to Aug 11
$135 total
Aug 10 - Aug 11
Total includes taxes and fees
8.6/10 Excellent! (1,004 reviews)
"Another Holiday Inn Express excellent experience."

Reviewed on Aug 1, 2025

Holiday Inn Express Hotel & Suites Auburn by IHG
See all 317 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.

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Frequently asked questions

How much does a Dudley vacation package cost?
You'll find cheap prices from $283 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.