Vacation Rentals

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Waterfront Deck Area has 3 Chaise Lounge and 2 Chairs not shown in this Photo

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CENCP

East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$6,000 - $9,700

Clean Fee:

$480 per week

Tax: State & Local:

11.7

Rates reduced for available weeks - see calendar for adjusted rates

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CENCR

Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$3,000 - $4,000

Clean Fee:

$480 per week

Tax: State & Local:

11.7

Ferry Ticket Available 8/10 week. (mv) Please inquire for details.

Rate reduced for week of 8/10 due to a cancellation - see calendar for adjusted rate

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CHA22

Gorgeous New Build, Contemporary Farmhouse Design, Heated Pool, Large Yard & Lawn Area, Sleeps 9, 3 bedrooms + Bonus Sleep Space on Lower Level, 3 Baths, 2 Half Baths

Luxurious new custom-built Katama area home with heated 14’ x 30’ pool. Ideally located just one mile to the village center and 1.5 miles to South Beach! Bike paths in...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,900 - $7,000

Clean Fee:

$700 per week

Tax: State & Local:

11.7

Owner reduced rates for September & October - see calendar for adjusted rates

Three night minimum first two weeks of June 2025 and after September 6th

Pool Heated to 81 degrees, included in rental rate July & August weeks.

Pool Heated to 81 degrees June & September weeks additional $300 per week propane surcharge.

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CHAMV

WATER VIEW, IN TOWN - 2 MINUTE WALK TO MAIN ST, WIFI, A/C

In-Town Luxury Home. This state-of-the-art home features a large living room with a dining area and a gourmet kitchen with Viking and Sub Zero appliances. Each of the 4 bedrooms...Read more

Location:

Vineyard Haven

Sleeps:

Bedrooms:

Baths:

Price Range:

$5,250 - $9,650

Clean Fee:

$450 per week

Tax: State & Local:

11.7

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CHOAY

Gorgeous Luxury Home, Edgartown, Heated Pool, Pickle Ball Court, Multiple Living Spaces, 4 Bedrooms. 4.5 Baths Sleeps 9.

This stunning contemporary vacation home in Edgartown offers an exceptional blend of indoor and outdoor living spaces, making it an ideal retreat for relaxation and entertainment. The beautifully landscaped yard features...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Baths:

Price Range:

$12,000 - $15,000

Clean Fee:

$1000 per week

Tax: State & Local:

11.7

Transferrable ferry tickets available 8/24-8/31. Please inquire for details! (mv)

Rates just reduced for available weeks in July & August - see calendar for adjusted rates

Pool Heat additional $250 per week June & September

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CLARA

Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Family and friends are sure to enjoy this pristinely maintained and spacious home situated in a private and quiet location. Beautiful yard and deck area with outdoor seating and a patio dining area that...Read more

Location:

Vineyard Haven

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,000 - $5,500

Clean Fee:

$700 per week

Tax: State & Local:

11.7

Ferry Tickets available for the weeks 8/10-8/17, 8/24-8/31 - please inquire

Rate just reduced for week of 8/10-8/17 - see calendar for adjusted rate

Sheets & Towels are not provided. Rental guests need to bring sheets & towels or they can be rented and delivered per the instructions from the linen rental company. www.marthaslinenrental.com

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CLARO

Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Situated just on the outskirts of Oak Bluffs, this lovely vacation home offers renters modern styling with multiple living spaces and all the conveniences renters look for in a vacation home....Read more

Location:

Oak Bluffs

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,800 - $6,100

Clean Fee:

$450 per week

Tax: State & Local:

11.7

New Bedrooms 3 & 4, in the lower level, and bath are not available in 2025 for the weeks 7/5 & 8/23 and September. Occupancy limit is 6, 2 Bedrooms 1st and 2nd Level. Sleep sofa and a day bed in the 2nd level family room. Rates listed reflect this arrangement for 2025. Inquire with Agent for details.

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CLE20

Outer Harbor Waterfront, Private Sandy Beach, Lush Gardens and Large Yard, Magnificent Water Views

Relax and enjoy the picturesque views of the outer harbor, with its plethora of boats going by each day, from the screened Gazebo, porch, and patio areas. The wide, sandy private beach...Read more

Location:

Vineyard Haven

Sleeps:

Bedrooms:

Baths:

Price Range:

$4,500 - $9,400

Clean Fee:

$600 per week

Tax: State & Local:

11.7

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CLEME

Sweetened Water Farm, 1 Mile from Village Center, Bike or Walk to Town

Lovely 4 bedroom, 2 bath home. Located just on the outskirts of Edgartown village center on Sweetened Water Farm (an 87-acre horse farm located near Morning Glory Farm). This spacious...Read more

Location:

Edgartown

Sleeps:

Bedrooms:

Baths:

Price Range:

$2,500 - $6,200

Clean Fee:

$300 per week

Tax: State & Local:

11.7

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COHAH