Martha's Vineyard Vacation Rentals Late Summer Weeks

 

Our Top 10 Picks For The Best Martha's Vineyard Vacation Rentals with late summer weeks available in August and September. We've curated a collection of our best vacation rentals in Edgartown, Katama, Vineyard Haven, and Oak Bluffs, 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 

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discount tag Available Peak Weeks August 2025


Some of the biggest events of the summer on Martha's Vineyard are moving a week later next year. The Agricultural Fair, Illumination Night, and the Oak Bluffs Fireworks are ALL moving to the third week of August in 2025 (August 15 - 24). This past summer, all those peak week events occurred during the second week. Given the popularity of that week, plus the other big events of August, lots of Martha's Vineyard vacation rentals are booked by repeat renters or get rented quickly. Good news, we've got a great collection of luxury homes that are available for next August. You can browse the collection here or call our Rental Team to explore your options 508.939.9422

Classic With A Modern Twist: In-Town Luxury Getaway $4,000 - $13,500/week

  • Property Highlights
    Unit Code: VH MMIC-29
    Pets Considered: No
    Town/Area: Vineyard Haven
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:10
  • Description:
    POINT B EXCLUSIVE - This new home is a modern take on a Classic Greek Revival and it has it all -- three living levels... Read More
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Luxurious Oak Bluffs Contemporary With Water Views $5,500 - $13,000/week

  • Property Highlights
    Unit Code: OB EVAN-07
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:4.5
    • Sleeps:8
  • Description:
    POINT B EXCLUSIVE - This freshly renovated Luxurious Contemporary combines water views out to Sengekontacket Pond from... Read More
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Edgartown Village Cape With Cozy Guest Cottage $5,450 - $9,950/week

  • Property Highlights
    Unit Code: EDG SMAC-10
    Pets Considered: Yes
    Town/Area: Edgartown - Village
    • Bedrooms:3
    • Bath:4.0
    • Sleeps:7
  • Description:
    POINT B EXCLUSIVE - While maintaining much of its historic charm, including wide plank floors and vintage fireplaces,... Read More
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The Whale House: Long Point Retreat $2,750 - $7,500/week

  • Property Highlights
    Unit Code: WT MALD-159
    Pets Considered: Yes
    Town/Area: West Tisbury
    • Bedrooms:4
    • Bath:3.0
    • Sleeps:9
  • Description:
    POINT B EXCLUSIVE - Privately set near Long Point Beach, The Whale House is a beautifully appointed, coastal-inspired... Read More
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Katama Coastal Getaway $2,500 - $7,500/week

  • Property Highlights
    Unit Code: KAT JMYE-29
    Pets Considered: No
    Town/Area: Edgartown - Katama
    • Bedrooms:3
    • Bath:2.0
    • Sleeps:6
  • Description:
    POINT B EXCLUSIVE - *Special Offer: Save Up To 15% On All Open Weeks* (new rates programmed). Tucked away in a quiet... Read More
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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
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The Ferry House On Edgartown Harbor $6,000 - $30,000 Per Week

  • Property Highlights
    Unit Code: EDG DMAL-04
    Pets Considered: Yes
    Town/Area: Edgartown - Village
    • Bedrooms:3
    • Bath:3.0
    • Sleeps:6
  • Description:
    With its spectacular waterfront setting, The Ferry House literally sits directly on Edgartown Harbor. There are sweeping... Read More
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Centrally Located Colonial In Oak Bluffs $3,500 - $8,000 Per Week

  • Property Highlights
    Unit Code: OB JGLE-23
    Pets Considered: No
    Town/Area: Oak Bluffs
    • Bedrooms:4
    • Bath:3.0
    • Sleeps:8
  • Description:
    Conveniently located near The Lagoon and Eastville Beach, this large Oak Bluffs Colonial has been refreshed with new... Read More
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The Cottage On Cooke Street $2,000 - $7,900 Per Week

  • Property Highlights
    Unit Code: EDG SFUL-59
    Pets Considered: No
    Town/Area: Edgartown - Village
    • Bedrooms:3
    • Bath:1.5
    • Sleeps:6
  • Description:
    This newly renovated Cottage on Cooke Street sits in the heart of historic Edgartown Village. The single-level Cottage... Read More
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