East Dennis Vacations from $849

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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.

The Latest East Dennis vacation packages

Price found within the past 48 hours. Click for updated prices.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $1,265, price is now $849 per person
$849
per person
Jul 21 - Jul 26
found 14 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (1,009 reviews)
Clean room, helpful staff!

Reviewed on May 5, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $4,498, price is now $2,771 per person
$2,771
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,411, price is now $907 per person
$907
per person
Jul 13 - Jul 18
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (77 reviews)
New hotel, very good curation of products and decor. Staff is very friendly.

Reviewed on May 7, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was $1,520, price is now $989 per person
$989
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

The Hotel Portsmouth

The Hotel Portsmouth

3 out of 5
Downtown
Save 100% on your flight
Price was $1,323, price is now $896 per person
$896
per person
Jul 19 - Jul 25
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (1,000 reviews)
Beautifully kept old style hotel. Great woodwork natural light, sitting rooms with fireplaces. Rooms are clean and well maintained, nice breakfast/ buffet. Excellent location

Reviewed on May 8, 2026

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Discover the most popular places to visit in East Dennis

Cape Cod Rail Trail

4.5/5(8 reviews)

Enjoy a trip to Cape Cod Rail Trail and popular activities like golfing in South Dennis. Wander the beautiful beaches and waterfront in this family-friendly area.

Cape Cod Rail Trail

What to do in East Dennis

Cape Cod Self-Guided Driving Audio Tour

Cape Cod Self-Guided Driving Audio Tour

$17
per traveler
100% of travellers recommend
Cape Cod Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
See all activities in East Dennis

East Dennis Hotel Deals

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
1421 Main Street Dennis MA
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $212 total per night from May 12 to May 13
$212 total
May 12 - May 13
Total with taxes and fees
9.6/10 Exceptional! (178 reviews)
We only stayed for 2 quick nights, but the property is lovely and impeccably maintained. The fact that the owner, Phil, is onsite and shares his personal cell phone is great. They also share a different text line for any needs that arise during your stay. We were able to get to various parts of the ...

Reviewed on Oct 13, 2025

Sesuit Harbor House
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
$202 nightly
The price is $231 total per night from May 17 to May 18
$231 total
May 17 - May 18
Total with taxes and fees
8.6/10 Excellent! (559 reviews)
👌

Reviewed on May 6, 2026

Margaritaville Resort Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $153 total per night from May 10 to May 11
$153 total
May 10 - May 11
Total with taxes and fees
8.8/10 Excellent! (1,538 reviews)
Good

Reviewed on May 1, 2026

Bayside Resort Hotel
See all 5,710 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.

Find the Best East Dennis Vacation Packages

East Dennis Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Barnstable Municipal Airport (HYA)
Population
2,800
Max Temp Winter
40ºF
Max Temp Summer
70ºF

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Frequently asked questions

How much does an East Dennis vacation package cost?
Offering excellent value package deals from $849 on Expedia, you'll be pleasantly surprised at how much a vacation to East Dennis costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to East Dennis?
If you're looking to book a cheap East Dennis vacation package, consider planning a trip in October, November and December. You're likely to find better rates on hotels and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for East Dennis?
With a well-organized itinerary, you can easily tick off the top East Dennis sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your East Dennis vacation for longer.
How to find the best East Dennis package deals?
Begin your search for an East Dennis package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect East Dennis package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your East Dennis escape off to a flying start.
Is it cheaper to book an East Dennis vacation as a package?
You can enjoy significant savings on your next East Dennis retreat by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to East Dennis?
Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment East Dennis escape.
Does Expedia offer Book Now, Pay Later East Dennis vacation packages?
Your East Dennis break is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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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.