Top Oak Bluffs Hotel Deals

Make the Most of Your Oak Bluffs Stay

Victorian charm meets coastal heritage

Oak Bluffs distinguishes itself through its extraordinary collection of over 300 Gingerbread Cottages, Victorian structures painted in vivid colors that originated as a Methodist camp meeting site in the 1800s. The Carpenter Gothic architecture creates an almost storybook atmosphere, particularly around the historic Tabernacle. The Flying Horses Carousel, America's oldest platform carousel dating to 1876, continues to delight visitors with its hand-carved horses and traditional brass ring game.

Cultural significance and waterfront energy

The town holds profound importance as a historic haven for African American families, with Inkwell Beach serving as a cultural gathering place for over a century. Circuit Avenue anchors the downtown with its concentration of restaurants, shops, and evening entertainment, while Ocean Park's 7-acre green space provides a grand entrance from the ferry terminal. The dining scene ranges from waterfront institutions like Nancy's Restaurant to refined spots such as Red Cat Kitchen, showcasing local seafood and island produce.

Practical considerations

The Vineyard Transit Authority connects Oak Bluffs efficiently to other island towns, though business travelers often prefer private car services for reliability. Martha's Vineyard Airport sits 7 miles away, with seasonal service from major carriers. The town's central location makes it an ideal base for exploring Edgartown or taking the inter-island ferry to Nantucket.

Frequently Asked Questions about Oak Bluffs

Can I use my miles on Delta Stays to book hotels in Oak Bluffs?

Yes, you can use your Delta miles to book your Oak Bluffs hotel stay, or you can combine your miles with cash for more flexibility. When you log in to your Delta SkyMiles® account, you will also discover Member offers at select properties that could enhance your travel experience.

What is the benefit of booking my Oak Bluffs hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 you spend on completed hotel stays and vacation rentals booked through Delta Stays. You will also enjoy access to special Member offers at select properties, and have the flexibility to pay with miles, cash, or a combination of both. Simply sign in to your SkyMiles account or enter your SkyMiles number at checkout when paying with cash to ensure you earn your miles. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies vary by property. We suggest reviewing the cancellation policies displayed in the detailed information for each hotel before completing your reservation. You'll find that some rates are refundable, while others are non-refundable. Changes and cancellations to your booking may result in a different amount of miles earned and awarded to your account.

Can I use my Delta SkyMiles® American Express® Card to book?

As a Delta SkyMiles® Gold, Platinum, or Reserve American Express® Cardholder, you can earn additional miles along with valuable benefits, including an annual statement credit of up to $200 applicable toward prepaid accommodations booked through Delta Cars and Stays. Terms apply. For an overview of all advantages associated with your card membership, please visit the Delta SkyMiles® American Express Credit Cards page where you can review complete benefit details.

Can I earn MQDs on Delta Stays hotel bookings?

Delta Stays occasionally offers valued promotions allowing SkyMiles Members to accumulate Medallion® Qualification Dollars when booking accommodations through their platform. We encourage you to visit the Delta Stays MQD Offer page to check for the latest MQDs offers and review their specific terms and conditions.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

No, Delta Stays accommodations are accessible to all travelers seeking hotel reservations. Nevertheless, enrollment as a SkyMiles Member provides you with opportunities to accumulate miles and gain access to preferential pricing and promotions available only to Members. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and other fees). The best part is that SkyMiles is free to join. Become a Member today by visiting the delta.com.

Can I book a vacation rental through Delta Stays?

Yes, in addition to traditional hotels, Delta Stays provides an extensive collection of vacation rentals for your vacation. You have access to numerous homes, condos, and specialty lodging options powered by Vrbo to suit your travel preferences. You can discover these alternative accommodations by visiting the Vacation Rentals page.

What hotels in Oak Bluffs have high ratings?

You will find 10 hotels in Oak Bluffs to choose from when you book on Delta Stays. Summercamp has a guest rating of 9.2 out of 10, and features a snack bar/deli and concierge services.

What's a good time of year to visit Oak Bluffs?

To experience Martha's Vineyard during great weather, visit in July when temperatures average in the mid-70s with sunny skies and key island events. For off-peak prices and hotel deals, consider May or September when temperatures remain pleasant, crowds thin out, and rates drop significantly.

Which hotels in Oak Bluffs are near Inkwell Beach?

Inkwell Beach has welcomed African American families since the 1800s, offering calm waters and cultural heritage. Join the "Polar Bears" for their cherished morning swim tradition. Harbor View Hotel is a popular hotel, which is just a short drive away. Another hotel is Vineyard Square Hotel & Suites and it is within a short drive.

Which hotels in Oak Bluffs are located closest to Oak Bluffs Harbor?

Oak Bluffs Harbor buzzes with maritime energy where sailboats bob alongside waterfront restaurants. Book one of the 80 slips ahead during summer months. Popular hotels include Harbor View Hotel which is a short drive away. Vineyard Square Hotel & Suites is another well-reviewed hotel and it is within a short drive.

Which hotels in Oak Bluffs are located closest to Oak Bluffs Town Beach?

The Inkwell Beach has welcomed African American families for generations, offering calm waters and sandy shores. Join the morning Polar Bears swimming group for a local tradition. Harbor View Hotel is a popular hotel, which is just a short drive away. Another top hotel is Vineyard Square Hotel & Suites and it is within a short drive.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar