Dudley Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Hotel Ivy Boston Common
Bay Village
Price was CA $1,447, price is now CA $924 per person
CA $924
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
Great accommodations if you are simply looking for just a place to lay your head without the bell and whistles of the major hotels. The location is walking distance to the a lot of major locations in the city.
Reviewed on May 12, 2026
The Langham, Boston
Downtown Boston
Price was CA $1,908, price is now CA $1,255 per person
CA $1,255
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had
Reviewed on May 2, 2026
Dudley Hotel Deals
Wellsworth Hotel
14 Mechanic St Southbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from May 24 to May 25
CA $133
CA $149 total
May 24 - May 25
includes taxes & fees
9.2/10 Wonderful! (1,506 reviews)
Very clean, staff very nice
Reviewed on May 10, 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 $107 per night from May 24 to May 25
CA $107
CA $120 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (1,656 reviews)
Lovely place to stay and the warmth and feel of an old Inn is wonderful. Happy and hope to return for a longer stay some day.
Reviewed on May 11, 2026
Comfort Inn Auburn - Worcester
426 Southbridge St Auburn MA
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from May 24 to May 25
CA $154
CA $172 total
May 24 - May 25
includes taxes & fees
7.8/10 Good! (1,135 reviews)
Too expensive
Reviewed on May 8, 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.
