Dudley Vacations from $395

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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.
Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
Price was $683, price is now $395 per person
$395
per person
Feb 12 - Feb 17
found 12 hours ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
15.2/10 Exceptional! (2,303 reviews)
Great value right on lakefront and super nice staff!!

Reviewed on Nov 16, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Price was $1,646, price is now $848 per person
$848
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
18.8/10 Exceptional! (460 reviews)
I haven’t stayed in a hotel this amazing for a long while! Everything about it was perfect, the staff, the facilities, the location / we had a room with a small kitchen area for a week and it was worth it. We hardly saw any other guests, and definitely didn’t hear anyone / it was a fantastic stay, had the gym to myself and there’s laundry facilities on most floors, I honestly didn’t want to leave! I would highly recommend to anyone visiting the area. The area itself has tons of shops and restaurants and feels very safe.

Reviewed on Nov 20, 2025

The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $880, price is now $511 per person
$511
per person
Dec 31 - Jan 6
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
18.8/10 Exceptional! (1,002 reviews)
The people and relaxing atmosphere were superb. Also a very comfortable bed.

Reviewed on Nov 20, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Save 100% on your flight
Price was $1,618, price is now $949 per person
$949
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
19.2/10 Exceptional! (482 reviews)
The room was wonderful, the bed was heaven. Room service was delicious and the overall aesthetic and ambience of the lobby and common areas were fabulous

Reviewed on Nov 18, 2025

Hotel 1620 Plymouth Harbor

Hotel 1620 Plymouth Harbor

3 out of 5
Plymouth Downtown Waterfront District
Save 100% on your flight
Price was $842, price is now $513 per person
$513
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
16.4/10 Exceptional! (1,000 reviews)
Great stay clean friendly and kids loved splash pad and pool!

Reviewed on Nov 19, 2025

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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
$89 nightly
The price is $100 total per night from Nov 23 to Nov 24
$100 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (1,557 reviews)
Love it

Reviewed on Nov 20, 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
$107 nightly
The price is $120 total per night from Dec 1 to Dec 2
$120 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,337 reviews)
Amazing stay

Reviewed on Nov 15, 2025

Wellsworth Hotel
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
$123 nightly
The price is $141 total per night from Dec 14 to Dec 15
$141 total
Dec 14 - Dec 15
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
Great location, polite and helpful staff the room was great, everything worked properly.

Reviewed on Nov 17, 2025

Hilton Garden Inn Worcester
See all 340 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 $395 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.