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.
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
Save 100% on your flight
Price was $757, price is now $500 per person
$500
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
8.8/10 Excellent! (1,007 reviews)
good place, location, room was nicely decorated; good bar and lobby

Reviewed on May 25, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $7,421, price is now $4,739 per person
$4,739
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Save 100% on your flight
Price was $1,064, price is now $699 per person
$699
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,451 reviews)
The location was perfect for me. I got there early and they got the room available as soon as possible. The manager went up to do a pre release inspection.

Reviewed on May 27, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $2,055, price is now $1,368 per person
$1,368
per person
Jul 29 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Fantastic Hotel. Loved the location, room was clean, staff was helpful, and loved the amenities.

Reviewed on May 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,637, price is now $1,139 per person
$1,139
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Gorgeous property, excellent restaurants and the staff was very attentive and very kind....we'll definitely be back the next time we visit Boston! We loved our stay!

Reviewed on May 26, 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

Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
$108 nightly
The price is $121 total per night from May 28 to May 29
$121 total
May 28 - May 29
Total with taxes and fees
9.2/10 Wonderful! (1,520 reviews)
"Clean Room, Quick Check in"

Reviewed on May 26, 2026

Wellsworth Hotel
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 Jun 9 to Jun 10
$89 total
Jun 9 - Jun 10
Total with taxes and fees
9/10 Wonderful! (1,652 reviews)
"I almost never write hotel reviews. Typically, the hotels are less than expected. This was exactly the opposite--a stay that exceeded our expectations in every way. The room was spacious, with beds and linens of good quality. We had a fabulous dinner at the Publick House restaurant, and then pastries ..."

Reviewed on May 27, 2026

Publick House Historic Inn and Country Motor Lodge
Spark By Hilton Northborough

Spark By Hilton Northborough

3 out of 5
27 Belmont Street Northborough MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Jun 21 to Jun 22
$118 total
Jun 21 - Jun 22
Total with taxes and fees
9/10 Wonderful! (84 reviews)
"Clean"

Reviewed on May 25, 2026

Spark By Hilton Northborough
See all 352 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.