Chappaquiddick Island Romantic Vacations 2026 | Expedia

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Top Romantic vacation packages in Chappaquiddick Island

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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$671

per person

Oct 23 - Oct 25

found 20 hours ago

Roundtrip flight included

Atlanta (ATL) to Hyannis (HYA)

8.6/10 Excellent! (733 reviews)

Harbor View Hotel

Harbor View Hotel

$1,986

per person

Oct 16 - Oct 20

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$2,165

per person

Oct 16 - Oct 20

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$2,095

per person

Oct 23 - Oct 25

found 8 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Hyannis (HYA)

9.4/10 Exceptional! (270 reviews)

Best resort

Reviewed on Sep 9, 2026

Doubletree by Hilton Cape Cod - Hyannis

Doubletree by Hilton Cape Cod - Hyannis

$898

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Hyannis (HYA)

8.4/10 Very Good! (943 reviews)

The pool outside was nowhere near the size in the photos. The inside pool was closed until 4pm so we could not get a swim and that’s why we booked this hotel. The outdoor pool was not only small but also unclean Very disappointed in this hotel.

Reviewed on Sep 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chappaquiddick Island

5* Romantic vacations in Chappaquiddick Island

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

Harbor View Hotel

Harbor View Hotel

$1,986

per person

Oct 16 - Oct 20

found 16 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$2,095

per person

Oct 23 - Oct 25

found 8 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Hyannis (HYA)

9.4/10 Exceptional! (270 reviews)

Best resort

Reviewed on Sep 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chappaquiddick Island

3 Night Romantic vacations in Chappaquiddick Island

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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

$776

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hyannis (HYA)

8.6/10 Excellent! (733 reviews)

Harbor View Hotel

Harbor View Hotel

$2,012

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$2,202

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chappaquiddick Island

4 Night Romantic vacations in Chappaquiddick Island

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

Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,526

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

9/10 Wonderful! (1,000 reviews)

The Faraway hotel in Edgartown is one of the nicest hotels on Martha's Vineyard. The location is unbeatable. They have their own parking lot which is key on the island. From the time you walk into the stunning lobby you are met by attentive staff and the hotels own signature fragrance. The rooms are spacious, updated and very clean. And the pool is an oasis in itself. I wouldn't stay anywhere else on the island.

Reviewed on Sep 8, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

Save 100% on your flight

$3,123

per person

Oct 10 - Oct 14

found 6 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Hyannis (HYA)

9.4/10 Exceptional! (270 reviews)

Best resort

Reviewed on Sep 9, 2026

Harbor View Hotel

Harbor View Hotel

$1,754

per person

Dec 4 - Dec 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Chappaquiddick Island

How can I find the best Chappaquiddick Island vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Chappaquiddick Island romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .

How can I plan a great romantic trip to Chappaquiddick Island?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Chappaquiddick Island?

Put a price on love with stunning deals for duos starting at just $671. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.

Can I book Chappaquiddick Island spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

What’s the best time of year for a romantic vacation in Chappaquiddick Island?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

How can I book romantic weekend getaway packages in Chappaquiddick Island?

To book a loved-up break in Chappaquiddick Island, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Chappaquiddick Island with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Chappaquiddick Island romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Things to do

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$50

per adult

Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50

per traveler

Marthas Vineyard Luxury Tour

Marthas Vineyard Luxury Tour (2hrs)

$550

per traveler

See all activities in Chappaquiddick Island

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Chappaquiddick Island Vacations

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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