Name: Wellsworth Hotel
Price range: CA $161

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.

The Westin Boston Seaport District

Seaport District

CA $577

per person

Oct 29 - Nov 1

found 22 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

9/10 Wonderful! (2,130 reviews)

Great hotel in a nice area. It’s not too far from the airport. They have a conference center so they do host events. Breakfast buffet was really good. There’s a Starbucks as well. They have a restaurant and laugh Boston on sight. Staff was great and accommodating. Just good experience overall. I recommend if you’re visiting Boston.

Reviewed on Sep. 2, 2025

Boston Harbor Hotel

North End

CA $784

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Boston (BOS)

9.8/10 Exceptional! (1,013 reviews)

Great harbor views! Room service was superb as well. Everyday we came back to an organized room and sometimes sweets, creams. The reception desk was also good in answering any questions. Excellent location. Would stay again.

Reviewed on Sep. 3, 2025

Raffles Boston

Back Bay

CA $2,080

per person

Oct 9 - Oct 13

found 9 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

9.6/10 Exceptional! (154 reviews)

Staff went above and beyond everyday! The dining options and location were amazing.

Reviewed on Sep. 2, 2025

Staypineapple, A Delightful Hotel, South End

South End

CA $637

per person

Oct 11 - Oct 13

found 21 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

8.8/10 Excellent! (1,001 reviews)

Rooms are very small, restaurant bar was just below our room and open til 1am-very loud, restaurant for breakfast has very limited menu and coffee is terrible.

Reviewed on Sep. 1, 2025

Maverick Suites at 245 Newbury St

Back Bay

CA $672

per person

Oct 29 - Nov 1

found 22 hours ago

Roundtrip flight included

Detroit (DTW) to Boston (BOS)

8.2/10 Very Good! (139 reviews)

Clean. Great location.

Reviewed on Jul. 31, 2025

Ready to book your vacation to Dudley?

Choose your dates

Dudley Hotel Deals

Publick House Historic Inn and Country Motor Lodge

277 Main Street (RT 131), Sturbridge, MA

Fully refundableReserve now, pay when you stay

CA $123

CA $137 total

Sep 7 - Sep 8

includes taxes & fees

Wellsworth Hotel

14 Mechanic St, Southbridge, MA

Fully refundableReserve now, pay when you stay

CA $161

CA $180 total

Sep 14 - Sep 15

includes taxes & fees

Sturbridge Host Hotel & Conference Center

366 Main St, Sturbridge, MA

Fully refundableReserve now, pay when you stay

CA $151

CA $169 total

Sep 7 - Sep 8

includes taxes & fees

See all 319 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.