Marthas Vineyard Cottages - Vacation Rentals in Sister Bay Beach

Cottage on the Hill From US $663
         

New
House
  • Air Conditioner
  • Parking
  • View
Tuckaway Cottage by Simple Life Rentals From US $367
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Updated Home w/Deck: 2 Mi to Sister Bay Beach! From US $322
         

9.8 (52 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Private Nature Retreat With Game Room From US $573
         

9.8 (10 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • TV
Experience True Door County Charm! From US $362
         

10.0 (34 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Three Sisters Cottage Barn Retreat From US $384
         

9.8 (28 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Sister Bay Beachside Hideaway, Location, Location! From US $366
         

5.0 (15 Reviews)
Cottage
  • Air Conditioner
  • View
  • Ocean View
Quiet and Serene, Central Location, Dog Friendly! From US $442
         

10.0 (67 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Beach Lane Lake House From US $382
         

10.0 (1 Review)
Cottage
  • TV
  • Security/Safety
  • Bedding/Linens
Charming 2-bedroom cottage in peaceful quiet neighborhood in Sister Bay From US $304
         

10.0 (1 Review)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Right Across From Beach And Park! From US $300
         

New
Cottage
  • TV
  • Bedding/Linens
  • Child Friendly
Pro Tip: Marthasvineyardcottages makes it easy to compare the best listings on Marthasvineyardcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Marthasvineyardcottages 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 Sister Bay Beach.

Weather in Sister Bay Beach

View the weather forecast for Sister Bay Beach before booking your Sister Bay Beach 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

Sister Bay Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Sister Bay Beach?
How many vacation rentals are available in Sister Bay Beach?

Currently, the total number of properties listed in 2026 is over 24 in the Sister Bay Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Sister Bay Beach.