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Chilmark Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

The Franklin Hotel Martha's Vineyard
Price was $1,443, price is now $1,336 per person
$1,336
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.

Vineyard Harbor Motel - Private Beach
Price was $2,111, price is now $1,929 per person
$1,929
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.

Harbor View Hotel
Price was $2,984, price is now $2,795 per person
$2,795
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.

Faraway Martha's Vineyard
Price was $1,507, price is now $1,414 per person
$1,414
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
I enjoyed my stay in the Chappy House – Room 409, a suite with its on entrance from the outside. It was very well appointed and similar to a spacious one bedroom apartment without the kitchen. Must be capable of maneuvering stone pathways and steps to access it. Very nice for a long-term stay. I’d be interested in purchasing one! (Luxury vinyl plank flooring needs repairing in one hallway spot — barely noticeable.) 🙂
Reviewed on Aug 20, 2026

The Christopher, The Edgartown Collection
Price was $2,622, price is now $2,476 per person
$2,476
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Vineyard Haven (MVY)
Stay at this B&B in Edgartown. Enjoy free breakfast, free WiFi, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Vincent House Museum are located nearby.

Morgan Hotel
Price was $2,433, price is now $2,307 per person
$2,307
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (MDW) 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.
I enjoyed my one night stay at the Morgan Hotel, previous to my arrival I received communication via text to give me the instructions of how to check-in. The instructions were clear and concise and easy to follow. My room was nice and clean it had a microwave and there were plenty towels and I received a complimentary beach bag and water bottles. The amenities offered were super convenient some of which included the cutest little ice machine, coffee, plates, plasticware, cups, etc. Housekeeping staff were very pleasant and accommodating and there were plenty of nearby dining and shopping options. Overall it was a great experience and I would definitely stay there again, I wholeheartedly recommend the Morgan Hotel.
Reviewed on Aug 27, 2026

The Island Inn on Martha's Vineyard
Price was $1,510, price is now $1,467 per person
$1,467
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) 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 Attleboro House
Price was $2,118, price is now $2,091 per person
$2,091
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Vineyard Haven (MVY)
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, housekeeping, and air conditioning. Popular attractions Inkwell Beach and Cottage Museum are located nearby.
The property sits where all the action is. The room is very clean however the bed mattress gave us severe back problems. The mattress needs to be change because we were stuck in the middle like a taco. The host flipped it but the mattresses needed to be replaced. The property is straight to the point with needing somewhere to sleep and bathe and the host was lovely but to save my back maybe not.
Reviewed on Jul 16, 2026
Chilmark Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



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