
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.

Anchor In Distinctive Waterfront Lodging
Price was $1,876, price is now $1,670 per person
$1,670
per person
Oct 9 - Oct 14
found 15 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Hyannis (HYA)
My daughter and I stayed at the Anchor In and had the most wonderful, relaxing experience from the time we arrived to checkout. We were greeted by Christine and Mary who were so welcoming and friendly. Our room was very clean and the Cape Cod decor and furniture were beautiful. The property is very well-maintained and provided us magnificent views of the harbor and pool.
The next day at breakfast we met Dale who was the most delightful host. We enjoyed our conversations with Dale and looked forward to seeing her at breakfast.
The front desk staff provided awesome service. Christine responded quickly to my room request. We also met Sandi who recommended and called a nearby restaurant to check on availability. She also offered to take pictures of us on the outdoor deck with the harbor in the background.
We had an amazing time at the Anchor In and can’t wait to return!
Reviewed on Aug 26, 2026

Faraway Martha's Vineyard
Price was $2,649, price is now $2,270 per person
$2,270
per person
Oct 4 - Oct 10
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) 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


The Franklin Hotel Martha's Vineyard
Price was $2,256, price is now $1,976 per person
$1,976
per person
Oct 4 - Oct 10
found 21 hours ago
Roundtrip flight included
Raleigh (RDU) 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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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.

