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A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark
Massachusetts
United States of America
North America
Hotwire.com

Chilmark Flight + Hotel Packages

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

Vineyard Harbor Motel - Private Beach

2.5 out of 5

Price was $713, price is now $616 per person

$616

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Book a stay at this beach motel in Vineyard Haven. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Inkwell Beach and Woods Hole Ferry Terminal are located nearby.

Thanks!

Reviewed on Oct 15, 2026

Harbor View Hotel

5 out of 5

Price was $874, price is now $754 per person

$754

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Book a stay at this luxury hotel in Edgartown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Edgartown Lighthouse are located nearby.

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 Island Inn on Martha's Vineyard

2.5 out of 5

Price was $818, price is now $709 per person

$709

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Book a stay at this golf resort in Oak Bluffs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Inkwell Beach and Farm Neck Golf Club are located nearby.

The Franklin Hotel Martha's Vineyard

2 out of 5

Price was $732, price is now $673 per person

$673

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Stay at this hotel in Edgartown. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Inkwell Beach and Edgartown Public Library are located nearby.

Faraway Martha's Vineyard

4 out of 5

Price was $836, price is now $774 per person

$774

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Book a stay at this business-friendly hotel in Edgartown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Vincent House Museum are located nearby.

Morgan Hotel

2.5 out of 5

Price was $696, price is now $651 per person

$651

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Stay at this hotel in Oak Bluffs. Enjoy free WiFi, concierge services, and cable TV channels. Popular attractions Inkwell Beach and Circuit Avenue are located nearby.

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

3 out of 5

Price was $804, price is now $755 per person

$755

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

St. Louis (STL) to Vineyard Haven (MVY)

Stay at this hotel in Edgartown. Enjoy free WiFi, free parking, and room service. Popular attractions Inkwell Beach and Edgartown Public Library are located nearby.