Dukes County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Dukes County

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

Edgartown

Top hotels in Dukes County

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road Vineyard Haven MA
The price is 7.873.359 ₫ per night from 19 Jul to 20 Jul
7.873.359 ₫
8.794.542 ₫ total
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (655 reviews)
"Clean, basic room; good appliances; friendly, helpful staff; on-site parking; fabulous ocean views with lots of boat activity. Prettier than the website pictures. Small bathroom—no counter space—but with fabulous shower head. Thin-ish walls. Location is 5-minute walk to ferry, diversity of restaurants, ..."

Reviewed on 27 Jun 2026

Vineyard Harbor Motel - Private Beach
Summercamp

Summercamp

3.5 out of 5
70 Lake Avenue Oak Bluffs MA
The price is 12.786.088 ₫ per night from 12 Jul to 13 Jul
12.786.088 ₫
14.282.061 ₫ total
12 Jul - 13 Jul
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Bathrooms are small and the sinks are extremely tiny"

Reviewed on 27 Jun 2026

Summercamp
MV Surfside Hotel

MV Surfside Hotel

2.5 out of 5
7 Oak Bluffs Avenue Oak Bluffs MA
The price is 8.300.175 ₫ per night from 1 Jul to 2 Jul
8.300.175 ₫
9.928.810 ₫ total
1 Jul - 2 Jul
includes taxes & fees
8.8/10 Excellent! (855 reviews)
"We enjoyed our stay at the MV Surfside Hotel. The staff is the primary reason our visit was so relaxing and comfortable. It was evident that everyone works very hard to maintain the facility and provide excellent guest services. The location adds value to the experience. It takes approximately three ..."

Reviewed on 27 Jun 2026

MV Surfside Hotel
See all 1,155 properties in Dukes County
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.

Frequently asked questions

How much does a Dukes County holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Dukes County from just . And the more you bundle, the more dollars you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Dukes County?
Combine your bookings with Expedia to save big bucks on your next getaway. With over 550 partner airlines and 1null000null000 hotels throughout the world, your Dukes County holiday package can be customized exactly to suit your travel style. With all that extra cash, why not throw in one or more awesome tours and experiences? It's an easy way to unlock even more savings. That holiday you've always dreamed of in Dukes County is closer than you thought!
What are the top hotels in Dukes County?
If you're on your way to Gosnold, you can't beat Mansion House Inn And Spa and Summercamp. Both are comfortable bases for exploring this vibrant Dukes County city.
How far in advance should I book my Dukes County holiday?
It depends on the air carrier, but you can generally browse through international fares on Expedia nearly a year in advance. While it's generally a good idea to book ahead of time, lucky customers will sometimes nab a cheaper seat just weeks before the date of departure.
What does an Expedia Dukes County travel package include?
It all comes down to what type of getaway you have in the works. Dukes County travel deals can include car rentals, hotels and flights. You can mix and match to create the travel package that suits you. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Dukes County travel package?
Get set to save with an Expedia travel package. Bundle your flights, rental cars and hotels and be rewarded with exciting discounts. You're not limited to hotels, however. Book with us and select from island resorts, rural cottages and everything in between!
Can I choose my airline with a Dukes County Expedia holiday package?
Yes, you can. Expedia has access to more than 550 partner airlines around the world, so pick the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my Dukes County holiday package?
If your holiday plans in Dukes County have changed, it's good to know that it is possible to cancel or amend your booking. If you made your booking within the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose fees. For more information, visit our Customer Service Portal.

Stay near popular Dukes County attractions

A beach with a lifeguard tower, a rocky breakwater, and the ocean.

Inkwell Beach

9.0/5 (154 reviews)
If a restful holiday is part of your travel plans, Inkwell Beach might be the perfect place to visit during your trip to Oak Bluffs. Stroll along this relaxing area's waterfront or simply enjoy its wineries.
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