Large Vacation Rentals & Suites for Group Travel

There are a lot of options in Oak Bluffs. If you plan on staying in the Oak Bluffs area, consider making a reservation for a few nights at one of these properties as these have been rated the top Group Travel Rental in Oak Bluffs:

• In-Town Certified National Historic Oak Bluffs Property -
• Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
• Multiple Ensuites, Central Air, Perfect Location
• ART FILLED BEACH COTTAGE IN THE PRIVATE WATERFRONT COMMUNITY OF WATERVIEW FARMS!
• Close to town, beautifully updated
• Martha's Vineyard Beachfront Condo in Oak Bluffs
• Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
• Historic Home in East Chop
• Beautiful Landscaped Grounds and Pond & Kayaks
• Location, Charm, & Steps to Town/Beach - Central AC, 100% Renewable Energy

Visit Rentthecottages group rental listings, click length of stay, enter your weekly or monthly stay in Oak Bluffs, and then enter the date and destination for your next group getaway. Filter on those places that accommodate more than 10 people for the largest places.

We have many pet-friendly long-term & short-term rentals available in Oak Bluffs . The Top pet-friendly rentals in Oak Bluffs are:

• Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
• Treeside Lodge
• The Attleboro House
• Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

Yes, there are more than 487 vacation rentals for multi-family or groups in Oak Bluffs that have indoor and private swimming pools. Check out our filter option and find your best-extended stay near Oak Bluffs.

Most of the group holiday rentals on Rentthecottages have internet facilities.