Our Top 10 Picks For The Best Martha's Vineyard Vacation Rentals for September and October. Late summer and early fall are some of the best times to visit Martha's Vineyard. We've curated a collection of our best vacation rentals in Edgartown, Katama, Oak Bluffs, and Vineyard Haven, from ultra-luxurious to vacation rentals with pools and water views, to budget-friendly. Our Rental Team is here to help and happy to match you with the best option(s). You can reach us at 508-627-4567 ext 1 or email us rentals@pointbrealty.com 

Martha's Vineyard Vacation Rentals September & October

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  • Property Highlights
    Unit Code: EDG BROS-09
    Pets Considered: Yes
    Town/Area: Edgartown - Other
    • Bedrooms:7
    • Bath:5.5
    • Sleeps:14
  • Description:
    Point B Exclusive - Tucked away in the prestigious Oyster Pond enclave, this post and beam country estate has luxurious... Read More
  • Property Highlights
    Unit Code: KAT SZOO-17
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:5
    • Bath:4.5
    • Sleeps:9
  • Description:
    Point B Exclusive - Located in the highly-coveted Edgartown Bay Road area of Katama -- and a stone's throw away from the... Read More
  • Property Highlights
    Unit Code: KAT CPAT-05
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath:3.5
    • Sleeps:8
  • Description:
    Point B Exclusive - This luxurious new Gambrel is designed for the indoor-outdoor Vineyard lifestyle, with a modern... Read More
  • Property Highlights
    Unit Code: KAT CSPA-09
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath:3.5
    • Sleeps:10
  • Description:
    Point B Exclusive - This newly built Modern Farmhouse with pool and hot tub sits in a quiet neighborhood in the heart of... Read More

Sleek Contemporary In Hidden Cove $5,000 - $14,000/week

  • Property Highlights
    Unit Code: OB ABON-15
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:6
    • Bath:5.5
    • Sleeps:12
  • Description:
    Point B Exclusive - This sleek new Contemporary is tucked away in the Hidden Cove neighborhood, just off Sengekontacket... Read More

Custom Cape In Edgartown With Hot Tub $10,000 - $14,000/week

  • Property Highlights
    Unit Code: EDG DSET-63
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    Point B Exclusive - This recently renovated Cape with farmer's porch is being newly furnished throughout and has a new... Read More
  • Property Highlights
    Unit Code: OB KMCD-09
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:5
    • Bath:4.5
    • Sleeps:10
  • Description:
    Point B Exclusive - BRAND NEW FOR SUMMER 2021 - This brand new Farmhouse with Connected Carriage House features a modern... Read More
  • Property Highlights
    Unit Code: VH LBRA-34
    Pets Considered: Yes
    Town/Area: Vineyard Haven
    • Bedrooms:6
    • Bath:4.0
    • Sleeps:10
  • Description:
    Point B Exclusive - BRAND NEW FOR SUMMER 2021 - This Luxurious New Contemporary is quietly tucked away by The Lagoon and... Read More

Garden Getaway With Pool $5,000 - $9,500/week

  • Property Highlights
    Unit Code: EDG JSTU-03
    Pets Considered: No
    Town/Area: Edgartown - Other
    • Bedrooms:3
    • Bath:2.0
    • Sleeps:6
  • Description:
    Point B Exclusive - Set in a quiet, wooded lot, and surrounded by beautiful manicured grounds and gardens, this recently... Read More
  • Property Highlights
    Unit Code: KAT SGAM-14
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:4
    • Bath:3.5
    • Sleeps:8
  • Description:
    Point B Exclusive - This Contemporary Farmhouse with attached Carriage House has been recently renovated and stylishly... Read More
  • Property Highlights
    Unit Code: EDG EONE-37
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:3
    • Bath:2.5
    • Sleeps:7
  • Description:
    Point B Exclusive - Located in the heart of Edgartown, this renovated Classic Village Cottage is just steps away from... Read More

Water View Cottage At Sunset Lake $5,000 - $7,500/week

  • Property Highlights
    Unit Code: OB MLLO-14
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:3
    • Bath:2.0
    • Sleeps:6
  • Description:
    Point B Exclusive -- This classic Oak Bluffs cottage sits at the edge of Sunset Lake and enjoys views across the Lake on... Read More