Chappaquiddick Island Vacation Packages

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Top Chappaquiddick Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was CA $1,882, price is now CA $1,489 per person
CA $1,489
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Hyannis (HYA)
9.4/10 Exceptional! (1,004 reviews)
They were very nice. The room was clean. The lobby and breakfast area were great. The breakfast selection had a wide variety and I appreciated that as a diabetic who cannot have a lot of the high carb selections. My husband DID enjoy the delicious looking muffins/cake slices.

Reviewed on Jun 23, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was CA $2,225, price is now CA $1,508 per person
CA $1,508
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Hyannis (HYA)
8.8/10 Excellent! (597 reviews)
Very nice property. Room was very good. Had all the amenities you need for a good comfortable stay. I would stay there again.

Reviewed on Jun 25, 2026

Chapter House

Chapter House

3.5 out of 5
Price was CA $2,131, price is now CA $1,594 per person
CA $1,594
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Hyannis (HYA)
9.2/10 Wonderful! (170 reviews)
DO NOT hesitate to book this beautiful Inn! Bill was so pleasant as soon as we entered the property! Will definitely stay again!

Reviewed on Jun 23, 2026

Inn on Main

Inn on Main

3.5 out of 5
Price was CA $2,355, price is now CA $1,823 per person
CA $1,823
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Hyannis (HYA)
10/10 Exceptional! (74 reviews)
I cannot recommend this property enough. David and Ruta are amazing hosts. They are so considerate and helpful. Breakfast is wonderful and they are more than willing to accommodate any dietary needs. The property is beautiful and well maintained. They have drawers full of travel supplies, and there are fresh baked cookies every day, in your room! The Inn is very well situated and walkable to some good restaurants (plan ahead to have dinner at the Old Yarmouth Inn). The Inn on Main is really not to be missed. Thank you for the amazing weekend!

Reviewed on Jun 22, 2026

Courtyard By Marriott Cape Cod Hyannis

Courtyard By Marriott Cape Cod Hyannis

3 out of 5
Price was CA $1,897, price is now CA $1,588 per person
CA $1,588
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTT) to Hyannis (HYA)
9/10 Wonderful! (502 reviews)
The hotel was clean and neat. The service was very good. I always enjoyed stay at this property.

Reviewed on May 30, 2026

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Chappaquiddick Island Hotel Deals

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $255 per night from Jul 26 to Jul 27
CA $255
CA $292 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (268 reviews)
"I did not use the amenities. The breakfast was nice. It was a comfortable, safe, clean place, good value for the dollar."

Reviewed on Jun 23, 2026

Iris Hotel Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is CA $529 per night from Jun 29 to Jun 30
CA $529
CA $686 total
Jun 29 - Jun 30
includes taxes & fees
7.8/10 Good! (329 reviews)
"We had an okay stay overall. The rooms were clean, and the restaurant was excellent. Unfortunately, one day during our visit the property lost power from 9:00 a.m. until 1:00 p.m., which was inconvenient. We stayed after Memorial Day and were disappointed to find that some of the advertised amenities, ..."

Reviewed on Jun 25, 2026

Sea Crest Beach Resort
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is CA $412 per night from Jul 27 to Jul 28
CA $412
CA $460 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (653 reviews)
"Everything good and clean the staff very helpful"

Reviewed on Jun 24, 2026

Vineyard Harbor Motel - Private Beach
See all 3,507 properties in Chappaquiddick Island
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.
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What to do in Chappaquiddick Island

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

CA $69
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chappaquiddick Island

Frequently asked questions

Can I cancel my flight booking to Chappaquiddick Island due to COVID-19?
Many airlines now offer greater flexibility due to COVID-19. Our convenient Customer Service Portal will help find an answer to most queries about which policies apply to your flight. It's also worth reading through the terms and conditions of your chosen carrier — preferably before locking in your seat!
What's the best way to find cheap flights to Chappaquiddick Island that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to deliver you the most flexible fares around town. Just tick the "No change fee" box directly under the "Flexible change policies" subheading to find your ideal flight to Chappaquiddick Island.
What are some of the general tips for travelers to Chappaquiddick Island during the COVID-19 outbreak?
The COVID-19 pandemic has changed how the world works in all sorts of ways, including our approach to travel. These tips will help you navigate these new challenges and prepare you for your escape to Chappaquiddick Island:
  • Before booking anything, see if any travel bans or restrictions apply — in both your origin and destination. Get up-to-date information by checking government and travel websites.
  • Wear a face mask during airport screening. A TSA employee will ask you to adjust your mask for identification purposes.
  • Do not hand your boarding pass directly to a TSA officer. Instead, position the pass on the scanner and then hold it up so the agent can inspect it.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will have to be removed from your bag for screening.
  • To minimize handling during screening, place items such as your phone, keys and wallet into your carry-on instead of into the bins.
  • Separate any food you're carrying for screening. Putting it in a clear plastic bag and into a bin reduces the need for a TSA employee to touch and inspect your belongings.

Which airlines fly to Chappaquiddick Island?
Reserve your ticket with Cape Air and then start piecing together your Chappaquiddick Island travel itinerary. This popular carrier runs 438 flights every month to Martha's Vineyard Airport (MVY), a key gateway.
How can I find cheap tickets to Chappaquiddick Island?
You'll always pick up an epic deal with Expedia, but our "flexible dates" search function makes it even easier. Enter your preferred travel date, then check the flexible dates box above to see the cheapest prices for nearby days. was the cheapest price for a flight to Chappaquiddick Island in the last seven days.
How much is a flight to Chappaquiddick Island?
There were lots of affordable fares for the taking in the last seven days, with the price of a return flight to Chappaquiddick Island ranging between and . Many lucky travelers nabbed one-way tickets from () for just .
What are the most popular airports to fly into in Chappaquiddick Island?
Pack your bags and fly into Martha's Vineyard Airport (MVY), Chappaquiddick Island's primary flight hub. Lock in a seat on one of the 838 flights that land at this awesome destination every month.
When is the cheapest time to fly to Chappaquiddick Island?
Consider traveling early on in the week to get a bargain fare to Chappaquiddick Island. Tuesday is routinely the most cost-effective day to fly, with Monday a close second. Saturday typically has the highest ticket prices. This is because lots of travelers choose to kick off their getaway on a weekend.
How much is a plane ticket to Chappaquiddick Island?
Plane tickets ranged from to over the last seven days. When you're ready to book, we're ready to help you pick up the best deal to Chappaquiddick Island.
Which airlines with flights to Chappaquiddick Island employ COVID-19 cleanliness policies?
In response to the COVID-19 pandemic, most airlines have implemented enhanced measures and standards to help their passengers and crew fly with extra peace of mind. Check out what these carriers are doing:
  • Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant.
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Tradewind Aviation - this airline is known for providing passenger masks and cleaning with disinfectant.

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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.