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

Find All Inclusive Resorts and Hotels in Oak Bluffs, MA

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Oak Bluffs All Inclusive Resorts and Hotels

Tonight
Sep 27 - Sep 28
Tomorrow
Sep 28 - Sep 29
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
No exact matches found, but these alternatives could be just right

Recommended hotels in Oak Bluffs

1. Summercamp

Summercamp
Oak Bluffs
CA $264
CA $295 total
includes taxes & fees
Oct 21 - Oct 22
Summercamp

2. Pequot Hotel

Pequot Hotel
Oak Bluffs
CA $281
CA $314 total
includes taxes & fees
Oct 5 - Oct 6
Pequot Hotel

3. The Attleboro House

The Attleboro House
Oak Bluffs
CA $237
CA $264 total
includes taxes & fees
Oct 14 - Oct 15
The Attleboro House

4. Morgan Hotel

Morgan Hotel
Oak Bluffs
CA $259
CA $289 total
includes taxes & fees
Oct 25 - Oct 26
Morgan Hotel

5. Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
CA $424
CA $755 total
includes taxes & fees
Oct 4 - Oct 5
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

6. Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town
Oak Bluffs
CA $559
CA $1,254 total
includes taxes & fees
Sep 28 - Sep 29
Vineyard Cottage Charm, Walk to Beach, On Bike Path, Near Town

7. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
CA $465
CA $883 total
includes taxes & fees
Sep 29 - Sep 30
Walk to Beach & Lighthouse: Oak Bluffs Studio!

8. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
CA $508
CA $1,190 total
includes taxes & fees
Sep 28 - Sep 29
Oak Bluffs 4BR • 5 Min Drive to Downtown

9. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
CA $563
CA $1,934 total
includes taxes & fees
Oct 1 - Oct 2
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

10. Brand New Guest house

Brand New Guest house
Oak Bluffs
CA $509
CA $1,679 total
includes taxes & fees
Oct 1 - Oct 2
Brand New Guest house
View all properties

Choose what matters most at all-inclusive hotels in Oak Bluffs

5 stars
4 stars
Adult-only
Pool
Family-friendly

Top Oak Bluffs Hotel Reviews

Frequently asked questions

How much does an all-inclusive hotel in Oak Bluffs cost?
Enjoy staying in an all-inclusive hotel in Oak Bluffs, with hotels from CA $264 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What area of Oak Bluffs is best for all-inclusive hotels?
Oak Bluffs, Massachusetts, is a delightful destination on Martha's Vineyard, known for its stunning beaches, vibrant community, and charming Victorian architecture. For travellers seeking all-inclusive hotels, the area near the Oak Bluffs Harbour stands out as the most convenient choice. This picturesque location not only offers easy access to the beach but also allows you to explore the local shops, restaurants, and the lively option of the town.Couples looking for a romantic retreat will appreciate the serene ambiance of the waterfront. Imagine enjoying sunset walks along the beach, followed by intimate dinners at nearby seafood restaurants that showcase the freshest catches of the day. Many all-inclusive options here also provide spa services and leisure activities, great for unwinding together.Families, too, will find Oak Bluffs appealing, especially with its range of family-friendly all-inclusive hotels. These accommodations often feature kid-friendly amenities, spacious rooms, and easy access to local attractions like the Flying Horses Carousel and the beautiful beaches. The area offers a laid-back atmosphere that ensures both parents and children can enjoy quality time together.
What is the best time to stay at an all-inclusive hotel in Oak Bluffs?
The best time to stay at an all-inclusive hotel in Oak Bluffs, Massachusetts, is during the summer months, particularly July and August. During this peak season, temperatures typically range from 20°C to 27°C, creating a warm and inviting environment for beachgoers and outdoor enthusiasts alike. The town buzzes with activity, as visitors flock to enjoy the sandy beaches, waterfront dining, and various festivals that take place throughout the summer.The pleasant summer weather makes it ideal for swimming, sailing, and exploring the scenic landscapes of Martha's Vineyard. Whether you're lounging by the ocean or taking a bike ride along the picturesque trails, the long days and sunny skies enhance the overall experience. However, do keep in mind that this is the busiest time of year, so booking accommodations and dining reservations in advance is advisable.If you're looking for a more budget-friendly option, consider visiting in September. The weather remains mild, with temperatures averaging around 22°C, but the crowds begin to thin out. This shoulder season offers a more relaxed atmosphere, allowing you to enjoy the local charm and engage with residents without the hustle and bustle of peak tourist season.
Is it cheaper to book an all-inclusive hotel and flight package in Oak Bluffs?
Booking an all-inclusive hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect all-inclusive travel package.
What all-inclusive amenities should we expect at hotels in Oak Bluffs?
All-inclusive hotels are perfect for travellers who want a relaxing, top-value vacation. Most packages include your room, all meals, snacks, unlimited drinks including alcohol and non-alcoholic drinks. Entertainment, kids' clubs, access to pools and fitness facilities are often included in the all-inclusive package as well. Some even cover airport transfers, while extras like spa treatments or premium alcohol may cost more. Knowing most of your expenses are already covered makes for a truly relaxing getaway. For more information, refer to the property details on Expedia.
Can I cancel my all-inclusive hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right all-inclusive hotel in Oak Bluffs for you.
How can I save on an all-inclusive hotel in Oak Bluffs with Expedia?
There are plenty of ways to save on an all-inclusive hotel in Oak Bluffs. Join One Key™, our free travel rewards program, to unlock instant discounts with Member Prices across a range of premium hotels. Typically, booking in advance will help you save on your hotel. If you're feeling spontaneous, be sure to check for last-minute deals.

Explore a world of travel with Expedia