Chappaquiddick Island Romantic Vacations

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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

$564
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.6/10 Excellent! (733 reviews)
Room as beautiful. There was a lot to do with young kids as well! Will come again. Great location to

Reviewed on Sep 8, 2026

Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$883
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
9.4/10 Exceptional! (270 reviews)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

$1,711
per person
Oct 12 - Oct 16
found 1 day 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

Harbor View Hotel

Harbor View Hotel

$1,734
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Doubletree by Hilton Cape Cod - Hyannis

Doubletree by Hilton Cape Cod - Hyannis

$1,347
per person
Nov 20 - Nov 22
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
8.4/10 Very Good! (938 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

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5* Romantic vacations in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$883
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
9.4/10 Exceptional! (270 reviews)
Harbor View Hotel

Harbor View Hotel

$1,734
per person
Oct 12 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
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3 Night Romantic vacations in Chappaquiddick Island

Price found within the past 48 hours. Click for updated prices.
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

$883
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hyannis (HYA)
9.4/10 Exceptional! (270 reviews)
Harbor View Hotel

Harbor View Hotel

$1,845
per person
Oct 22 - Oct 25
found 1 day 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

$1,740
per person
Oct 22 - Oct 25
found 1 day 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

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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 7 hours 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

Harbor View Hotel

Harbor View Hotel

$1,754
per person
Dec 4 - Dec 8
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

$1,614
per person
Dec 4 - Dec 8
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.4/10 Very Good! (53 reviews)
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How to find a romantic Chappaquiddick Island vacation

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.

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 $564. 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.

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 Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
Marthas Vineyard Luxury Tour

Marthas Vineyard Luxury Tour (2hrs)

$550
per traveler
Marthas Vineyard Luxury Tour (2hrs)
See all activities in Chappaquiddick Island

More vacations you might like

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