848+ Vacation Rentals Near Oak Bluffs Harbor |
  1. USA
  2. Massachusetts
  3. Oak Bluffs
  4. Oak Bluffs Harbor

Old Mansions - Vacation Rentals in Oak Bluffs Harbor

Property Image From $702
         

|
8.0 (1 Review)
House
Treeside Lodge
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $1,266
         

10.0 (71 Reviews)
House
Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $488
         

10.0 (21 Reviews)
Apartment
102 m² Apartment ∙ 2 bedrooms ∙ 4 guests
  • 1097 ft² Apartment
  • Air Conditioner
  • Parking
  • View

View Availability
Property Image From $265
         

9.8 (93 Reviews)
Hotel
The Attleboro House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

View Availability
Property Image From $1,520
         

|
New
Villa
** Vineyard Vacation Retreat ** with NEW HOT TUB
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $545
         

9.8 (52 Reviews)
House
Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $380
         

10.0 (17 Reviews)
Apartment
111 m² Apartment ∙ 2 bedrooms ∙ 6 guests
  • 1194 ft² Apartment
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $208
         

|
9.4 (1006 Reviews)
Hotel
Mansion House Inn And Spa
  • Air Conditioner
  • Pool
  • TV

View Availability
Property Image From $239
         

|
10.0 (4 Reviews)
Apartment
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
  • Parking
  • View
  • Ocean View

View Availability
Property Image From $541
         

9.8 (54 Reviews)
House
Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $367
         

10.0 (13 Reviews)
House
167 m² House ∙ 5 bedrooms ∙ 8 guests
  • 1797 ft² House
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $423
         

|
9.4 (527 Reviews)
Hotel
Pequot Hotel
  • Air Conditioner
  • Parking
  • View

View Availability
Property Image From $760
         

|
10.0 (2 Reviews)
House
Modern Family Home Walkable to Town
  • Air Conditioner
  • View
  • Security/Safety

View Availability
Property Image From $395
         

9.8 (24 Reviews)
House
Beautiful 3 bedroom 2 bath Home/Close to Town & Beach
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $224
         

|
10.0 (2 Reviews)
House
Marthas Vineyard Home Walk to Oak Bluffs Beach!
  • Parking
  • View
  • Ocean View

View Availability
Property Image From $847
         

8.6 (45 Reviews)
House
Dog-friendly home with fenced yard- walking distance to beach, ferry & town
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $434
         

|
10.0 (1 Review)
House
Oak Bluffs Darling
  • Air Conditioner
  • Parking
  • Pet Friendly

View Availability
Property Image From $371
         

9.4 (75 Reviews)
House
New Construction with Patio & Yard - Downtown & Beaches
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $378
         

|
10.0 (1 Review)
Apartment
Garage Suite
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

View Availability
Property Image From $1,065
         

9.4 (13 Reviews)
House
Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!
  • Air Conditioner
  • Parking
  • Pool

View Availability
Property Image From $244
         

|
10.0 (1 Review)
House
Less Than 1 Mi to Beaches Home with Deck in Oak Bluffs
  • Parking
  • Pet Friendly
  • Accessibility

View Availability
Property Image From $600
         

9.2 (7 Reviews)
House
Swim And Sunsets At The Lagoon! Conveniently Located 2 Miles From Town!
  • Parking
  • TV
  • Balcony/Terrace

View Availability
Property Image From $526
         

10.0 (21 Reviews)
House
Renovated 4 bedroom home in Vineyard Haven
  • Air Conditioner
  • Parking
  • TV

View Availability
Property Image From $407
         

9.4 (19 Reviews)
House
Conveniently located near Town
  • Air Conditioner
  • Parking
  • TV

View Availability
★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Oak Bluffs Harbor.

Weather in Oak Bluffs Harbor

View the weather forecast for Oak Bluffs Harbor before booking your Oak Bluffs Harbor Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Oak Bluffs Harbor, MA

Old Mansions offers a large selection of top attractions around Oak Bluffs Harbor. Research things to do on your vacation before you visit Oak Bluffs Harbor.


Old Silver Beach Inkwell Beach Falmouth Heights Beach Katama Beach Woods Hole Ferry Terminal Edgartown Lighthouse Oak Bluffs Town Beach Nobska Lighthouse Surf Drive Beach Martha's Vineyard Film Center Island Queen Ferry Cape Cod Beaches South Beach Martha's Vineyard Museum Martha's Vineyard Chamber of Commerce Woods Hole Oceanographic Institution Flying Horses Carousel Lighthouse Beach Island Cove Miniature Golf Gus Ben David's World of Reptiles and Birds Park