Chappaquiddick Island Vacation Packages 2025/2026 from $225

Chappaquiddick Island flight + hotel vacation packages

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

Hyannis Plaza Hotel

$225

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.

Anchor In Distinctive Waterfront Lodging

$379

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a snack bar/deli are also on offer.

Margaritaville Resort Cape Cod

$373

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

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.

Courtyard Resort

$268

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Free self parking and a computer station are also offered on site.

Holiday Inn Hyannis by IHG

$345

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

This hotel features an outdoor pool, an indoor pool, and a restaurant. Enjoy the gym and perks like free self parking and free WiFi. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Top Chappaquiddick Island hotels deals

Iris Hotel Cape Cod

291 Jones Rd, Falmouth, MA

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$158 total

Dec 4 - Dec 5

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Parking included

Falmouth Inn

824 Main Street, Route 28, Falmouth, MA

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$164 total

Nov 10 - Nov 11

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Faraway Martha's Vineyard

23 Kelly Street, Martha's Vineyard, Edgartown, MA

$247 nightly

$276 total

Nov 5 - Nov 6

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.

Pool

Pet friendly

Hyannis Travel Inn

18 North St, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$107 total

Nov 5 - Nov 6

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Enjoy the hot tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.

Pool

Hot Tub

Hyannis Harbor Hotel

213 Ocean St, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$174 total

Nov 5 - Nov 6

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.

Pool

Free WiFi

Sea Crest Beach Resort

350 Quaker Rd, North Falmouth, MA

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$166 total

Nov 17 - Nov 18

Total with taxes and fees

A private beach, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the picnic area.

On private beach

Pool

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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 Poge Lighthouse

Find out about the history of Edgartown when you spend time at Cape Poge Lighthouse. Wander the beautiful beaches and waterfront in the area.

Chappaquidick Dike Bridge

Find out about the history of Edgartown when you spend time at Chappaquidick Dike Bridge. Check out the wineries or top-notch restaurants in this walkable area.

Mytoi Garden

Explore the great outdoors at Mytoi Garden, a lovely green space in Edgartown. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Frequently asked questions

How much are vacation packages to Chappaquiddick Island?

Travelocity has flight and hotel packages from an incredible $225. With such huge savings, you'll be exploring all of Chappaquiddick Island in a flash.

Where can I get the best vacation package deals for Chappaquiddick Island?

Travelocity has all you need to score an awesome Chappaquiddick Island package deal. Take your pick of 400 partner airlines and 1,000,000 properties all over the globe and craft a vacation package that suits your style. With so many options at hand, you have inspiration galore for your next big adventure.

Why should I purchase my Chappaquiddick Island vacation bundle with Travelocity?

Whether you're in search of the ultimate unplugged getaway or after the fun and excitement of the big city, booking everything with Travelocity saves you time, hassle and money. No need to comb through hundreds of different websites to find the best deal — our Price Match Guarantee ensures you'll always score the lowest possible price, and our professional customer service experts are available 24/7.

Can I save money on my Chappaquiddick Island car rental if I combine it with hotels and flights?

You sure can with our Chappaquiddick Island vacation packages. With one of these, there are loads of ways to make your hard-earned cash go further. Combine any two or more car, hotel, flight and tour bookings and see the savings start to pile up. With your own set of wheels, all the landmarks around Chappaquiddick Island are within reach.