Dudley Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

Top Dudley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,504, price is now CA $667 per person
CA $667
per person
Dec 20 - Dec 23
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very good! (194 reviews)
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,120, price is now CA $1,142 per person
CA $1,142
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
!

Reviewed on Nov 10, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $1,556, price is now CA $1,032 per person
CA $1,032
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was CA $3,232, price is now CA $2,174 per person
CA $2,174
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was CA $1,890, price is now CA $1,305 per person
CA $1,305
per person
Jan 31 - Feb 3
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)

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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
The price is CA $126 per night from Nov 15 to Nov 16
CA $126
CA $141 total
Nov 15 - Nov 16
includes taxes & fees
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
The price is CA $130 per night from Dec 13 to Dec 14
CA $130
CA $146 total
Dec 13 - Dec 14
includes taxes & fees
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
The price is CA $116 per night from Nov 29 to Nov 30
CA $116
CA $130 total
Nov 29 - Nov 30
includes taxes & fees
La Quinta Inn by Wyndham Auburn Worcester
See all 398 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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Stay near popular Dudley attractions

Nichols College

Explore the campus of Nichols College during your stay in Dudley.
See properties

Frequently asked questions

How much does a Dudley vacation package cost?
You can snap up a vacation package to this popular destination from CA $667 on Expedia. However, how much your vacation to Dudley costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Dudley?
If you're hoping to score a cheap Dudley vacation package, consider visiting in January, February and November. You're likely to find better prices on airfares and hotels during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Dudley?
Usually, a handful of days is enough to tick off the top attractions during your Dudley vacation. But if you'd like to have some time to rest or take day trips, think about extending your itinerary.
How to find the best Dudley package deals?
Use Expedia's handy filters to find some great Dudley package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Dudley package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Dudley vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Dudley getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Dudley?
If you're planning a spontaneous Dudley trip, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Dudley?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite season and the available activities will also help you decide when to visit Dudley.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your accommodations will probably be the biggest expense during your trip to Dudley.
  3. Decide how long to go for: Now that you know more about Dudley, you can work out the perfect length of your vacation. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, lock in the perfect Dudley vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.