Name: Chatham Wayside Inn
Price range: CA $183
Rating: 9.2

Your East Dennis Vacation

Create a custom vacation package to East Dennis and get ready for your next great adventure. Base yourself in the neighborhood of Northwest Harwich, which is great for nature and walking, for a true taste of this unique city. There's plenty to see and do during a trip to East Dennis, including Cape Cod Rail Trail and Eden Hand Arts. Whatever your travel plans or the size of your budget, organizing your ultimate tailored East Dennis vacation is a breeze with Expedia.

Top East Dennis Vacation Deals

Price found within the past 48 hours. Click for updated prices.

The Colonnade Hotel Back Bay

Back Bay

CA $800

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.2/10 Wonderful! (2,268 reviews)

Easy check in, courteous staff, clean rm and great view. Prudential mall across Huntington Ave..

Reviewed on Feb 2, 2026

Boston Harbor Hotel

North End

CA $1,643

per person

Apr 29 - May 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Langham, Boston

Downtown Boston

CA $1,072

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (1,004 reviews)

Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

Mandarin Oriental, Boston

Back Bay

CA $3,272

per person

Mar 30 - Apr 5

found 9 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Boston (BOS)

9.4/10 Exceptional! (376 reviews)

The rooms are spotless , staff are extremely welcoming. Everything and more you could want while staying in Boston

Reviewed on Feb 8, 2026

The Whitney Hotel

Beacon Hill

CA $1,005

per person

Mar 20 - Mar 23

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Boston (BOS)

9.6/10 Exceptional! (482 reviews)

Excellent property conveniently located in Beacon Hill. Rooms are a tad on the small side but well appointed and clean.

Reviewed on Feb 7, 2026

Ready to book your vacation to East Dennis?

Choose your dates

East Dennis Hotel Deals

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Fully refundableReserve now, pay when you stay

CA $211

CA $320 total

Feb 10 - Feb 11

includes taxes & fees

8.6/10 Excellent! (441 reviews)

Clean room, nice staff, the only problem was the internet was slow

Reviewed on Feb 2, 2026

Chatham Bars Inn

297 Shore Rd Chatham MA

CA $498

CA $570 total

Feb 11 - Feb 12

includes taxes & fees

9.2/10 Wonderful! (808 reviews)

Beautiful property

Reviewed on Jan 24, 2026

Chatham Wayside Inn

512 Main St Chatham MA

Fully refundableReserve now, pay when you stay

CA $183

CA $269 total

Feb 10 - Feb 11

includes taxes & fees

9.2/10 Wonderful! (630 reviews)

Courteous staff, helpful with dining suggestions. Loved the room. Very comfortable bed, warm and cozy.

Reviewed on Jan 29, 2026

See all 5,568 properties in East Dennis

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.