COVID-19 alert: Travel requirements are changing rapidly, including need for pre-travel COVID-19 testing and quarantine on arrival.

Oak Bluffs, MA Vacation Packages

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Oak Bluffs Vacation: Coronavirus Information

Most Oak Bluffs hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Oak Bluffs trip, please visit our Coronavirus Information page (opens in new window).

Top Oak Bluffs Flight + Hotel Deals

Inn on Main
Cape Codder Resort and Spa
Hyannis Host Inn
Hyannis Travel Inn
Chapter House

Top Hotels in Oak Bluffs

3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
Free CancellationReserve now, pay when you stay
The price is $149 per night from Apr 19 to Apr 20
4.5/5Wonderful! (311 reviews)
"It was a very good hotel. With a beautiful interior design, great location. We enjoyed a lot our time there"

Reviewed on Apr 15, 2021

MV Surfside Hotel
MV Surfside Hotel
2.5 out of 5
7 Oak Bluffs Avenue, Oak Bluffs, MA
The price is $159 per night from Apr 19 to Apr 20
4.4/5Excellent! (407 reviews)
"Clean quiet and close to everything. Loved our stay"

Reviewed on Jan 5, 2021

MV Surfside Hotel
Pequot Hotel
Pequot Hotel
3 out of 5
19 Pequot Avenue, Oak Bluffs, MA
The price is $99 per night from May 9 to May 10
4.5/5Wonderful! (240 reviews)
Pequot Inn on The Vineyard is excellently located
"Pequot went the extra smile, safe & sound & sane - was still able to provide a breakfast inclusion for guests that adhered to MA state standards while providing a lovely inclusion service that many hotels no longer offer or attempt to offer and yet those hotels taking away the breakfast inclusion ..."

Reviewed on Oct 14, 2020

Pequot Hotel
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.

Top things to do in Oak Bluffs

Oak Bluffs Beach Vacation

There's nothing like an Oak Bluffs vacation to put a spring in your step. The soothing rhythm of the ocean waves and the smell of clean ocean air are sure to rejuvenate your mind and body. To be close to the town center on your trip to Oak Bluffs, base yourself around Inkwell Beach (1 mile (2 km) away). If you're going to stay for a while, look into our Oak Bluffs vacation packages. Not only will you be able to save cash, you'll also have other beautiful beaches around you to explore, like Oak Bluffs Town Beach and Joseph Sylvia State Beach. We call that a win-win!

What are the advantages of a road trip to Oak Bluffs?

There’s nothing quite like a Oak Bluffs road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Oak Bluffs or bundle your hotels with car rentals to save even more. With our Oak Bluffs packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Oak Bluffs?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Oak Bluffs and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Oak Bluffs?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Oak Bluffs. You can book all the road trip activities on your Oak Bluffs wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Oak Bluffs. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does an Oak Bluffs vacation package cost?
Chart your own course with our Oak Bluffs vacation packages, which start from only $543. Select the hotels and flights that fit your travel plans. Then, add on a couple of activities or tours for an one-of-a-kind adventure.
If I'm not able to travel, can I cancel my Oak Bluffs vacation package?
You can change or cancel your booking, but whether you’ll incur a fee depends on a few things. If you’ve booked an Oak Bluffs vacation package in the last 24 hours, you may be able to change your itinerary for free. If it’s been more than 24 hours, your airline, hotel or car rental company may charge a fee. Browse our Customer Service Portal for further information.
How do I get a cheap travel package to Oak Bluffs?
Bundle your hotel and flight bookings, throw in extras such as tours, and save as much as $583. An Oak Bluffs vacation package makes getting away on a budget a walk in the park. You won’t just pick up awesome discounts on your getaway — you’ll have a huge amount of choice at your fingertips too. When you book through Expedia, you can choose from more than 550 airlines and 1,000,000 properties all over the world. Your unforgettable vacation begins right here, right now!
What are the top hotels in Oak Bluffs?
Sunset Meadows will be an excellent base for your Oak Bluffs escape. Located in Lagoon Heights, it’s one of the area’s leading hotels.
When is the best time of year to visit Oak Bluffs?
The ideal time to visit Oak Bluffs depends on you. If you’re vacationing on a smaller budget, you might want to avoid , which is considered to be the most expensive month. is usually when you’ll pick up the best prices. To enjoy the buzz of peak season, take off in . are the quietest months to visit and a good idea if you want to get away from the crowds.
How far in advance should I book my Oak Bluffs vacation?
Savvy travelers always book early. Airlines usually release flight tickets around a year ahead of departure, and this is an excellent opportunity to pick up some of the lowest prices. Boss just told you to use up your vacation time in a few weeks? That’s alright! Expedia are never short of fantastic bargains to help you have the getaway of your dreams, at an affordable price.
What does an Expedia Oak Bluffs travel package include?
Select from any combination of hotels, flights and rental cars. Once you’ve made your booking, you can add the fun stuff like tours and activities. Want to pick your airfare class? That’s also easy to do. The choice is all yours when it comes to arranging your dream Oak Bluffs trip.
What should I know before booking an Oak Bluffs travel package?
We already have low prices. However, you’ll score an even better deal if you book your hotels, flights and car rentals together. With an Expedia travel package, you’ll get transparent pricing and a huge range of choice.
Does Expedia offer Book Now, Pay Later Oak Bluffs vacation packages?
Thanks to our partnership with online lender Affirm, those booking via Expedia can now pay for their flights, hotels and more in manageable installments that won’t drain your wallet. Book Now, Pay Later and begin your big adventure today!
Can I choose my airline with an Oak Bluffs Expedia vacation package?
The choice is all yours! We offer more than 550 airlines around the world, so you can design your Oak Bluffs escape according to your budget and needs.

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