Dudley Vacation Packages
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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 Harbor Hotel
North End
Price was CA $3,342, price is now CA $2,076 per person
CA $2,076
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.
Reviewed on Mar 23, 2026
The Langham, Boston
Downtown Boston
Price was CA $2,837, price is now CA $1,836 per person
CA $1,836
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Room was spacious, clean & well set up. Nice that they use Dyptique hand soap shampoo & shower gel. That is a 5 star touch.
Bed was nice and very quiet location.
Reviewed on Mar 22, 2026
Fairmont Copley Plaza, Boston
Back Bay
Price was CA $2,731, price is now CA $1,935 per person
CA $1,935
per person
Jun 2 - Jun 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Boston (BOS)
9/10 Wonderful! (1,196 reviews)
Great experience here, staff was fantastic, rooms were clean and comfortable.
Reviewed on Mar 23, 2026
Dudley Hotel Deals
Wellsworth Hotel
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Mar 31 to Apr 1
CA $148
CA $165 total
Mar 31 - Apr 1
includes taxes & fees
9.2/10 Wonderful! (1,457 reviews)
Awesome
Reviewed on Mar 24, 2026
Publick House Historic Inn and Country Motor Lodge
277 Main Street (RT 131) Sturbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from Mar 30 to Mar 31
CA $111
CA $124 total
Mar 30 - Mar 31
includes taxes & fees
9/10 Wonderful! (1,620 reviews)
We were just there to sleep, got in late, left early. Beds were really comfortable and really nice pillows. Beds and bathroom really clean. We had a pet friendly room, which is nice to have as we had our dog. But room did smell of dog, and carpet not too fresh. Still all in all would stay again
Reviewed on Mar 26, 2026
Comfort Inn Auburn - Worcester
426 Southbridge St Auburn MA
Fully refundable
The price is CA $117 per night from Mar 30 to Mar 31
CA $117
CA $130 total
Mar 30 - Mar 31
includes taxes & fees
7.8/10 Good! (1,082 reviews)
Great room
Reviewed on Mar 22, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
