Oak Bluffs Town Beach Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.

Hyannis Plaza Hotel

$573

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

Margaritaville Resort Cape Cod

$1,129

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

Inn on Main

$1,255

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

It is a wonderful Inn and the owners truly care that you are happy there. Breakfast was amazing and other complementary items such as beer and wine along with snacks were greatly appreciated. It is right in the center of the town and there are nice walks to be had from the Inn's location. Very glad we stayed there.

Reviewed on Oct 21, 2026

Anchor In Distinctive Waterfront Lodging

$650

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

Courtyard Resort

$625

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

$633

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

Holiday Inn Hyannis by IHG

$599

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

The Villa Callo Inn

$1,360

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Hyannis (HYA)

John was amazing, made the whole experience worth it. Room was cozy and staff were attentive.

Reviewed on Sep 8, 2026

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Best Lodging Options Near Oak Bluffs Town Beach

Summercamp

70 Lake Avenue Oak Bluffs MA

0.38 km from Oak Bluffs Town Beach

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

0.17 km from Oak Bluffs Town Beach

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

0.38 km from Oak Bluffs Town Beach

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

0.32 km from Oak Bluffs Town Beach

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

19 Pequot Avenue Oak Bluffs MA

0.73 km from Oak Bluffs Town Beach

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

18 Kennebeck Avenue Oak Bluffs MA

0.35 km from Oak Bluffs Town Beach

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 ...

The Oak Bluffs Inn

64 Circuit Ave Oak Bluffs MA

0.59 km from Oak Bluffs Town Beach

Stay at this guesthouse in Oak Bluffs. Enjoy free WiFi, an airport shuttle (surcharge), and daily housekeeping. Popular attractions Inkwell Beach and Circuit ...

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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.