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.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $1,327, price is now $1,140 per person
$1,140
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,825, price is now $1,515 per person
$1,515
per person
Sep 28 - Oct 2
found 11 hours 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

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $2,115, price is now $1,879 per person
$1,879
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
Price was $1,922, price is now $1,721 per person
$1,721
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
Price was $1,741, price is now $1,564 per person
$1,564
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

The Sydney, The Edgartown Collection

The Sydney, The Edgartown Collection

3.5 out of 5
Price was $1,586, price is now $1,430 per person
$1,430
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
Great boutique hotel right near everything

Reviewed on Aug 28, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was $1,597, price is now $1,477 per person
$1,477
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)

The Edgartown Inn, The Edgartown Collection

The Edgartown Inn, The Edgartown Collection

3.5 out of 5
Price was $1,618, price is now $1,500 per person
$1,500
per person
Sep 28 - Oct 2
found 11 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Vineyard Haven (MVY)
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Reviewed on Aug 27, 2026

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Best Lodging Options Near Oak Bluffs Harbor

Summercamp

Summercamp

3.5 out of 5
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

MV Surfside Hotel

2.5 out of 5
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

Morgan Hotel

2.5 out of 5
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

The Attleboro House

2.5 out of 5
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 ...
Pequot Hotel

Pequot Hotel

3 out of 5
19 Pequot Avenue Oak Bluffs MA
0.87 km from Oak Bluffs Harbor
Stay at this hotel in Oak Bluffs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Madison Inn

Madison Inn

2.5 out of 5
18 Kennebeck Avenue Oak Bluffs MA
0.47 km from Oak Bluffs Harbor
Stay at this guesthouse in Oak Bluffs. Enjoy free WiFi, daily housekeeping, and a fireplace in the lobby. Popular attractions Inkwell Beach and Circuit Avenue ...
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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.