Flights To Dukes County - Cheap Flights Starting at CA $143

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An aerial view of a coastal area with a lighthouse, a sandy beach, and a marina.

Edgartown

Flights
Edgartown
A row of colorful, historic houses with a central path.

Oak Bluffs

Flights
Oak Bluffs

How Much Does it Cost To Fly To Dukes County?

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

Thu, Aug 20 - Wed, Aug 26
ORD
O'Hare Intl.
HYA
Barnstable Municipal
CA $323 Roundtrip, found 18 hours ago
CA $323
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Thu, Aug 20 from O'Hare Intl. to Barnstable Municipal, returning Wed, Aug 26, priced at CA $323 found 18 hours ago
Sat, Aug 22 - Sun, Aug 23
ORD
O'Hare Intl.
ACK
Nantucket Memorial
CA $461 Roundtrip, found 2 days ago
CA $461
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Aug 22 from O'Hare Intl. to Nantucket Memorial, returning Sun, Aug 23, priced at CA $461 found 2 days ago
Tue, Sep 1 - Sat, Sep 5
BTV
Burlington Intl.
MVY
Martha's Vineyard
CA $477 Roundtrip, found 1 day ago
CA $477
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 1 from Burlington Intl. to Martha's Vineyard, returning Sat, Sep 5, priced at CA $477 found 1 day ago
Wed, Sep 2 - Sat, Sep 5
BTV
Burlington Intl.
MVY
Martha's Vineyard
CA $488 Roundtrip, found 1 day ago
CA $488
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 2 from Burlington Intl. to Martha's Vineyard, returning Sat, Sep 5, priced at CA $488 found 1 day ago
Mon, Aug 31 - Sat, Sep 5
BTV
Burlington Intl.
MVY
Martha's Vineyard
CA $503 Roundtrip, found 1 day ago
CA $503
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Aug 31 from Burlington Intl. to Martha's Vineyard, returning Sat, Sep 5, priced at CA $503 found 1 day ago
Thu, Jul 16 - Mon, Jul 20
ORD
O'Hare Intl.
ACK
Nantucket Memorial
CA $574 Roundtrip, found 6 days ago
CA $574
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Jul 16 from O'Hare Intl. to Nantucket Memorial, returning Mon, Jul 20, priced at CA $574 found 6 days ago
Thu, Aug 13 - Mon, Aug 17
ORD
O'Hare Intl.
MVY
Martha's Vineyard
CA $582 Roundtrip, found 1 day ago
CA $582
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from O'Hare Intl. to Martha's Vineyard, returning Mon, Aug 17, priced at CA $582 found 1 day ago
Thu, Aug 13 - Mon, Aug 17
ORD
O'Hare Intl.
MVY
Martha's Vineyard
CA $598 Roundtrip, found 1 day ago
CA $598
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from O'Hare Intl. to Martha's Vineyard, returning Mon, Aug 17, priced at CA $598 found 1 day ago
Tue, Jul 28 - Wed, Aug 5
YUL
Pierre Elliott Trudeau Intl.
PVD
T.F. Green
CA $718 Roundtrip, found 5 days ago
CA $718
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jul 28 from Pierre Elliott Trudeau Intl. to T.F. Green, returning Wed, Aug 5, priced at CA $718 found 5 days ago
Wed, Jul 29 - Tue, Aug 4
YUL
Pierre Elliott Trudeau Intl.
PVD
T.F. Green
CA $859 Roundtrip, found 5 days ago
CA $859
Roundtrip
found 5 days ago
Select Air Canada flight, departing Wed, Jul 29 from Pierre Elliott Trudeau Intl. to T.F. Green, returning Tue, Aug 4, priced at CA $859 found 5 days ago
Thu, Jul 30 - Mon, Aug 3
YUL
Pierre Elliott Trudeau Intl.
PVD
T.F. Green
CA $881 Roundtrip, found 5 days ago
CA $881
Roundtrip
found 5 days ago
Select United flight, departing Thu, Jul 30 from Pierre Elliott Trudeau Intl. to T.F. Green, returning Mon, Aug 3, priced at CA $881 found 5 days ago
OriginDestinationTravel datesFlights from*
LGANantucketAugust 17 to August 21CA $294
DENNantucketAugust 29 to September 5CA $302
BOSNantucketSeptember 28 to October 1CA $322
JFKWarwickJuly 24 to July 25CA $345
IAHWarwickAugust 12 to August 18CA $346
JFKHyannisAugust 25 to September 2CA $357
JFKMassachusettsSeptember 1 to September 4CA $371
BOSHyannisJuly 24 to July 27CA $419
BOSWarwickAugust 14 to August 21CA $496
PHLNantucketAugust 28 to August 31CA $531
DENWarwickJuly 23 to July 27CA $716
DENMassachusettsSeptember 20 to September 27CA $1,903
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LGANantucketJuly 12 to July 16CA $402
BOSNantucketJuly 12 to July 15CA $530
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Atlantic Inn
3.5-star property

The Atlantic Inn

Jul 31 - Aug 3

3 night stay

Toronto (YYZ) to Providence (PVD)

United • Non-stop • Coach

Providence (PVD) to Toronto (YYZ)

Air Canada • Non-stop • Coach
Price was CA $2,437, price is now CA $1,689 per person
CA $1,689
per person
found 22 hours ago
Wayfinder Newport
4.0-star property

Wayfinder Newport

Jul 29 - Aug 3

5 night stay

Toronto (YYZ) to Providence (PVD)

Delta • Non-stop roundtrip • Coach
Price was CA $3,853, price is now CA $2,507 per person
CA $2,507
per person
found 18 hours ago
The Underwood-Hale House
4.0-star property

The Underwood-Hale House

Aug 11 - Aug 17

6 night stay

Toronto (YYZ) to Providence (PVD)

American Airlines • Non-stop roundtrip • Coach
Price was CA $2,857, price is now CA $1,989 per person
CA $1,989
per person
found 19 hours ago
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Travelers ❤️ These Dukes County 🏨

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
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 Oak Bluffs Harbor and Inkwell Beach are located nearby.
9/10 Wonderful! (669 reviews)
"I booked this motel through Expedia and paid more than 4 months in advance, expecting a quality room that matched the listing. Instead, I was extremely disappointed. The room was with a small window, about 75% of the view was completely blocked by a rusted metal building located only about 4 inches ..."

Reviewed on Jul 7, 2026

Opens in a new windowVineyard Harbor Motel - Private Beach
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
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 rooms in our reviews. Popular attractions Oak Bluffs Harbor and Inkwell Beach are located nearby.
9.4/10 Exceptional! (1,001 reviews)
"Amazing hotel in the perfect location! That staff made you feel so welcomed. The best part was having beach towels/chairs available to guests and the coffee, tea, and toys for the kids at no additional cost! I can’t say how much I loved it here enough!"

Reviewed on Jul 7, 2026

Opens in a new windowSummercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
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 Oak Bluffs Harbor and Inkwell Beach are located nearby.
8.8/10 Excellent! (861 reviews)
"close proximity to ferry, Circuit Ave and Inkwell."

Reviewed on Jul 8, 2026

Opens in a new windowMV Surfside Hotel
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Faraway Martha's Vineyard

Faraway Martha's Vineyard

4 out of 5
23 Kelly Street Edgartown MA
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 Oak Bluffs Harbor are located nearby.
9/10 Wonderful! (1,001 reviews)
"Be aware of theft at this hotel: I had an item stolen from my room by staff"

Reviewed on Jul 8, 2026

Opens in a new windowFaraway Martha's Vineyard
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.