Vacations Close To Oak Bluffs Harbor
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Oak Bluffs Harbor Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Cape Cod
Price was $1,088, price is now $933 per person
$933
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Hyannis (HYA)
Fantastic staff very helpful. Wife using a walker they accommodated us with a better room that she had easy access to.
Reviewed on Aug 27, 2026
Faraway Martha's Vineyard
Price was $1,792, price is now $1,483 per person
$1,483
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
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
Morgan Hotel
Price was $1,344, price is now $1,167 per person
$1,167
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
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 Franklin Hotel Martha's Vineyard
Price was $1,464, price is now $1,311 per person
$1,311
per person
Sep 28 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
Great place to stay. Very nice and private room. We stayed in room 19 and it had a private patio with a kitchenette in our room. Place was easy to find and had plenty of parking. Would recommend again
Reviewed on Aug 25, 2026
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View all tripsBest Lodging Options Near Oak Bluffs Harbor
Summercamp
70 Lake Avenue Oak Bluffs MA
0.25 km from Oak Bluffs Harbor
Book a stay at this beach hotel in Oak Bluffs. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
MV Surfside Hotel
7 Oak Bluffs Avenue Oak Bluffs MA
0.39 km from Oak Bluffs Harbor
Stay at this hotel in Oak Bluffs. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
Morgan Hotel
9 Healy Way Oak Bluffs MA
0.49 km from Oak Bluffs Harbor
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 ...
The Attleboro House
42 Lake Ave Oak Bluffs MA
0.3 km from Oak Bluffs Harbor
Stay at this hotel in Oak Bluffs. Enjoy free WiFi, housekeeping, and air conditioning. Popular attractions Inkwell Beach and Cottage Museum are located ...
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See all available properties in Oak Bluffs Harbor
View all propertiesLowest 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.