Deals on vacations and trips to East Dennis

Save when you book East Dennis package deals

Choose two or more items and save on your trip:

East Dennis flight + hotel vacation packages

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

The McKernan Inn

3 out of 5
Price was $807, price is now $619 per person
$619
per person
Feb 13 - Feb 16
found 1 hour ago
Roundtrip non-stop flight included
Kansas City (MCI) to Boston (BOS)
This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,474, price is now $1,030 per person
$1,030
per person
Feb 9 - Feb 12
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,185, price is now $868 per person
$868
per person
Feb 9 - Feb 12
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.
The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was $891, price is now $666 per person
$666
per person
Feb 9 - Feb 12
found 2 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a garden, and a lobby fireplace are also offered.

Top East Dennis hotels deals

Cozy Condo close to Sesuit

Cozy Condo close to Sesuit

Dennis MA
Get rates
This condo featured laundry facilities and barbecue grills.
Kitchen
Air conditioning
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
867 Iyannough Road Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$112 nightly
The price is $128 total per night
$128 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Pool
Breakfast included
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$196 nightly
The price is $224 total per night
$224 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Pool
Hot Tub
Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $85 total per night
$85 total
Dec 30 - Dec 31
Total with taxes and fees
This motel features an indoor pool and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the hot tub and perks like free self parking and free WiFi.
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$467 nightly
The price is $535 total per night
$535 total
Dec 30 - Dec 31
Total with taxes and fees
A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free valet parking and a free beach shuttle.
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28 West Yarmouth MA
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $114 total per night
$114 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Don't see what you're looking for?
See all available properties in East Dennis
View all properties
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.

Popular places to visit

Cape Cod Rail Trail

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

Frequently asked questions

How much are vacation packages to East Dennis?
With deals starting at just $619, hotel and flight packages are a fabulous way to make your vacation budget stretch further. East Dennis, here you come!
How long should my East Dennis vacation be?
If you're looking for some guidance, most visitors spend about 2 nights vacationing in East Dennis. But to uncover the true spirit of this destination, stay a few extra nights. You'll be able to get to more attractions and really immerse yourself in the local vibe.
Where can I get the best vacation package deals for East Dennis?
It's hard to beat Travelocity when it comes to piecing together your East Dennis package deal. There are as many as 400 partner airlines and 1,000,000 properties around the world to choose from. Book your vacation now and get ready to cross another amazing place off your travel bucket list.
Why should I purchase my East Dennis vacation bundle via Travelocity?
Because life is one amazing journey, and we offer everything you need to help you on your way. With our first-rate service and Price Match Guarantee, you can organize your trip with confidence. Plus, you can rest easy while you're on the road knowing we're always available to chat via our 24/7 support.
Can I save money on my East Dennis car rental if I combine it with hotels and flights?
With an East Dennis vacation package, you can bundle your hotel, car and flight bookings and save a nice amount. If you're in the mood to discover the best of this impressive region, why not head to Fenway Park? This famous attraction is 65 mi from East Dennis. With a rental car, you'll be there in a flash.
Which airport is best for East Dennis?
Logan Intl. Airport (BOS), around 60 mi northwest of downtown East Dennis, is most likely where you'll arrive. Your other choices are Martha's Vineyard Airport (MVY) (35 mi away from central East Dennis) and Nantucket Memorial Airport (ACK) (35 mi away from central East Dennis).
Where should I stay when visiting East Dennis?
Many visitors spend their nights at the Sesuit Harbor House. It's an excellent base for your East Dennis getaway.

Photos of local treasures

Browse East Dennis vacation photos for more inspiration

East Dennis
East Dennis
East Dennis
East Dennis
East Dennis