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.
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
Price was $601, price is now $532 per person
$532
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Great owner and great staff. Location was good. Helpful tips to get us around. Would definitely recommend. Thank you Liam and staff for making our extra memorable

Reviewed on Aug 25, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,168, price is now $935 per person
$935
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)

Chapter House

Chapter House

3.5 out of 5
Price was $1,364, price is now $1,111 per person
$1,111
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
A beautiful inn and lovely gardens and deck to enjoy. A bar and on some nights live music makes it even better.

Reviewed on Aug 21, 2026

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $1,328, price is now $1,084 per person
$1,084
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Old , run down. Pool shut during our stay. Overall , needs a massive renovation.

Reviewed on Aug 22, 2026

Heritage House Inn on Cape Cod, an Ascend Collection Hotel

Heritage House Inn on Cape Cod, an Ascend Collection Hotel

2.5 out of 5
Price was $727, price is now $619 per person
$619
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)

The Villa Callo Inn

The Villa Callo Inn

3 out of 5
Price was $1,405, price is now $1,229 per person
$1,229
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Really enjoyed our stay. Staff went above and beyond, breakfast was top notch and the Location was great.

Reviewed on Aug 11, 2026

Courtyard Resort

Courtyard Resort

2 out of 5
Price was $653, price is now $575 per person
$575
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

3 out of 5
Price was $907, price is now $825 per person
$825
per person
Sep 29 - Oct 4
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Hyannis (HYA)
Great location!

Reviewed on Aug 24, 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 Oak Bluffs Harbor 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.