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Oak Bluffs Vacation Packages

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Oak Bluffs Flight + Hotel Packages

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

Courtyard Resort

2 out of 5
Price was $786, price is now $701 per person
$701
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Book a stay at this business-friendly hotel in Hyannis. Enjoy free WiFi, free parking, and a garden. Popular attractions Hyannis Harbor and John F. Kennedy Hyannis Museum are located nearby.
Nice place. Staff was lovely.

Reviewed on Sep 25, 2026

Inn on Main

Inn on Main

3.5 out of 5
Price was $1,298, price is now $1,143 per person
$1,143
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Stay at this B&B in Yarmouth Port. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mayflower Beach and Hyannis Harbor are located nearby.
Very accommodating hosts , Dave & Ruta. Delicious 2 course breakfast.Room was clean, very comfortable and great amenities. Hosts were very helpful regarding dining and touring ideas. Highly recommend

Reviewed on Aug 8, 2026

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,293, price is now $1,144 per person
$1,144
per person
Nov 26 - Nov 29
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Book a stay at this spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions Hyannis Harbor and Cape Codder Water Park are located nearby.

Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $918, price is now $823 per person
$823
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Stay at this hotel in Hyannis. Enjoy free WiFi, an outdoor pool, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hyannis Harbor and Main Street Hyannis are located nearby.
No microwave in room. LG TV only had LG stations. Unusual for hotels these days. Breakfast was nice.

Reviewed on Sep 25, 2026

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Price was $1,800, price is now $1,623 per person
$1,623
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Book a stay at this beach motel in Vineyard Haven. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Inkwell Beach and Woods Hole Ferry Terminal are located nearby.
No additional comments.

Reviewed on Sep 25, 2026

Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $2,039, price is now $1,878 per person
$1,878
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Book a stay at this luxury hotel in Edgartown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Edgartown Lighthouse are located nearby.

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $2,009, price is now $1,855 per person
$1,855
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Book a stay at this golf resort in Oak Bluffs. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Inkwell Beach and Farm Neck Golf Club are located nearby.
Nice quaint hotel with easy access to transit. However, walking at night to restaurant was dark. $5 for a bag of ice to store where? No outside porch lights. Drain issue in shower but did report when checked out.

Reviewed on Sep 24, 2026

Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,858, price is now $1,720 per person
$1,720
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Book a stay at this business-friendly hotel in Edgartown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Inkwell Beach and Vincent House Museum are located nearby.

Oak Bluffs Vacation Packages 3-4 Night Stays

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

Courtyard Resort

2 out of 5
Price was $786, price is now $701 per person
$701
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Inn on Main

Inn on Main

3.5 out of 5
Price was $1,298, price is now $1,143 per person
$1,143
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
Price was $1,293, price is now $1,144 per person
$1,144
per person
Nov 26 - Nov 29
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)
Anchor In Distinctive Waterfront Lodging

Anchor In Distinctive Waterfront Lodging

3 out of 5
Price was $918, price is now $823 per person
$823
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Hyannis (HYA)

Oak Bluffs Vacation Packages 5-7 Night Stays

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 $1,800, price is now $1,623 per person
$1,623
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Harbor View Hotel

Harbor View Hotel

5 out of 5
Price was $2,039, price is now $1,878 per person
$1,878
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $2,009, price is now $1,855 per person
$1,855
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
Price was $1,858, price is now $1,720 per person
$1,720
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Mon, Oct 12 - Thu, Oct 15
JFK
John F. Kennedy Intl.
ACK
Nantucket Memorial
$403 Roundtrip, found 4 days ago
$403
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Oct 12 from John F. Kennedy Intl. to Nantucket Memorial, returning Thu, Oct 15, priced at $403 found 4 days ago
JetBlue Airways
Sun, Sep 27 - Thu, Oct 8
LGA
LaGuardia
ACK
Nantucket Memorial
$458 Roundtrip, found 4 days ago
$458
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sun, Sep 27 from LaGuardia to Nantucket Memorial, returning Thu, Oct 8, priced at $458 found 4 days ago
JetBlue Airways
Mon, Sep 28 - Tue, Oct 6
DCA
Ronald Reagan Washington National
ACK
Nantucket Memorial
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 28 from Ronald Reagan Washington National to Nantucket Memorial, returning Tue, Oct 6, priced at $514 found 1 day ago
JetBlue Airways
Thu, Oct 8 - Sun, Oct 11
JFK
John F. Kennedy Intl.
HYA
Barnstable Municipal
$570 Roundtrip, found 3 days ago
$570
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Oct 8 from John F. Kennedy Intl. to Barnstable Municipal, returning Sun, Oct 11, priced at $570 found 3 days ago