Cuttyhunk Vacation Packages 2026 from $998

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The Latest Cuttyhunk vacation packages

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

Vineyard Harbor Motel - Private Beach

$998

per person

Jan 5 - Jan 12

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Vineyard Haven (MVY)

9/10 Wonderful! (812 reviews)

Went to check in and the code given to me did not work. Called the property manager and no response for 3 straight days.

Reviewed on Oct 14, 2026

The Island Inn on Martha's Vineyard

$1,330

per person

Jan 5 - Jan 12

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Vineyard Haven (MVY)

8.2/10 Very Good! (58 reviews)

Faraway Martha's Vineyard

$1,327

per person

Jan 5 - Jan 12

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Vineyard Haven (MVY)

9/10 Wonderful! (1,001 reviews)

Harbor View Hotel

$1,339

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,001 reviews)

Beautiful Hotel and Venue with impeccable amenities. Beautiful water views and outstanding and friendly Staff. Disappointed we were not able to stay longer. Will definitely plan another trip in the near future!

Reviewed on Oct 10, 2026

The Franklin Hotel Martha's Vineyard

$1,077

per person

Jan 5 - Jan 12

found 16 hours ago

Roundtrip flight included

Chicago (ORD) to Vineyard Haven (MVY)

9.2/10 Wonderful! (215 reviews)

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Cuttyhunk Hotel Deals

New Bedford Harbor Hotel

222 Union St New Bedford MA

Fully refundableReserve now, pay when you stay

$127 nightly

$141 total

Oct 15 - Oct 16

Total with taxes and fees

8.2/10 Very Good! (1,015 reviews)

"Great place to stay if you’re in town"

Reviewed on Oct 13, 2026

Inn on the Square

40 North Main Street Falmouth MA

Fully refundableReserve now, pay when you stay

$142 nightly

$163 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (1,004 reviews)

"Great location. Nice rooms"

Reviewed on Oct 13, 2026

Vineyard Harbor Motel - Private Beach

60 Beach Road Vineyard Haven MA

$168 nightly

$188 total

Oct 22 - Oct 23

Total with taxes and fees

9/10 Wonderful! (825 reviews)

"Went to check in and the code given to me did not work. Called the property manager and no response for 3 straight days."

Reviewed on Oct 14, 2026

See all 1,213 properties in Cuttyhunk

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.