Oak Leaf Vacation Home in Oak Bluffs: Holiday Homes

Oak Bluffs stays: 4 holiday homes from $180/night. Oak Leaf Vacation Home & more with full kitchens, BBQ, and beach access. Book now.

Check-in
Fri, 25 Sept
Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 25 Sept
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Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
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Check-in
Fri, 25 Sept
-
Check-out
Sat, 26 Sept
Rooms and Guests2 Guests, 1 room
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1-4 out of 4
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  • Price: high to low
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Tiffany'S TreasureHoliday home
Map
2.3 mi from City Center
Hot TubPrivate GardenTable Tennis
  • Spacious four-bedroom holiday home
  • Private hot tub in garden
  • Fully equipped kitchen & BBQ
Select
Island SanctuaryHoliday home
7.6
Very good7 total reviews
our site & Booking.com
7 adults
3 bedrooms
4 beds
Map
1.1 mi from City Center1.1 mi from Oak Bluffs
FishingWindsurfingBeach Access
  • Private holiday home with garden
  • On-site fishing and windsurfing
  • Beach access with board games
FromUS$ 739 /nightSelect
Canary CottageHoliday home
7.8
Very good5 total reviews
our site & Booking.com
Map
607 yd from City Center517 yd from Oak Bluffs
PatioDishwasherPrivate Entrance
  • Private entrance for added privacy
  • Fully equipped kitchen with dishwasher
  • Patio with outdoor furniture and TV
FromUS$ 350 /nightSelect
6.5
Nice11 total reviews
our site & Booking.com
Map
1432 yd from City Center1368 yd from Oak Bluffs
FireplaceFull KitchenFishing
  • Three-bedroom home with fireplace
  • On-site fishing activity
  • Steps from Eastville Beach
FromUS$ 316 /nightSelect

Oak Bluffs, the vibrant heart of Martha's Vineyard, presents oak leaf vacation home options that put you close to the island's iconic gingerbread cottages and lively harbor. These holiday homes offer a more personal base than a standard hotel, with dedicated spaces for families and groups. Visitors can expect fully equipped kitchens, private entrances, and outdoor living areas designed for soaking up the island's relaxed atmosphere. Options like the Island Sanctuary include a garden and balcony, while Tiffany's Treasure adds a hot tub for unwinding after a day of exploration.

Choosing a holiday home in Oak Bluffs means having the freedom to cook local seafood, spread out across multiple bedrooms, and live at your own pace. The Canary Cottage, a five-bedroom home, is a 13-minute walk from Oak Bluffs Town Beach. For those needing airport access, Martha's Vineyard Airport is just 4 km away, and properties like Yellow Brick Road House place you within a kilometer of Eastville Beach. While oak leaf vacation home properties vary in size and price, budgeting around $180-350 per night offers a range of options with parking, free WiFi, and non-smoking rooms, ensuring your island base feels both practical and refreshing.