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Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $6,500
June 2025
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July 2025
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$6,500
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$6,500
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 $8,000
August 2025
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$8,000
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$8,000
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$8,000
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$8,000
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$6,500
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 $4,500
September 2025
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,500
June 2025
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July 2025
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$6,100
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$6,100
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 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,500
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$6,500
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$6,900
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$6,500
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$6,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
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$6,500
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$5,500
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$4,700
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$4,700
28
29
30
 
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
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Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,500 - $6,500
June 2025
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July 2025
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$10,000
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$8,500
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31
 $13,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$13,500
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$13,500
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$13,500
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$13,500
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$9,350
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
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$7,000
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$6,500
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$6,500
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$6,500
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Rates just reduced for available weeks in July & August by 15% - see calendar for adjusted rates

 

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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Perfect Katama Location. 4 bedrooms, Spacious Deck overlooking Yard Area

Situated in the heart of the Katama area of Edgartown this lovely home is just 2 miles to South Beach and 2 miles to the heart of Edgartown village area. ...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,900 - $6,500
June 2025
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July 2025
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 1
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3
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$6,200
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$6,500
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31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
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$6,500
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$6,800
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$6,800
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$6,800
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$6,800
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
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$6,500
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$5,900
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$5,900
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Clean Fee: 
$425
Tax: State & Local: 
11.7
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Beautiful Oak Bluffs home just blocks from the Center of Town, Ocean Park and Inkwell Beach.

Note: the kitchen is being completely remodeled for summer 2024 and will have all new high-end appliances, Subzero, Thermador, and new cabinets, and counters. 

Summer Joy!  Set in the heart of...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,000 - $6,500
June 2025
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July 2025
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$8,000
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$8,000
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 $8,750
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,750
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$8,750
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$10,350
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$10,350
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$8,750
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$6,500
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 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

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

 

8-minute walk from the ferry dock in Oak Bluffs and 5 minute walk to the Ink Well Beach, and Oak Bluffs Center from the house. 

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Wonderful Vacation Home, East Chop Area of Oak Bluffs, Private Yard, Screened Porch, 4 bedrooms, 2 baths.

Nestled on a quiet street in the idyllic East Chop area of Oak Bluffs, this classic New England summer home offers vacationing families and friends a special place to gather...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,200 - $6,500
June 2025
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July 2025
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$5,500
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$5,500
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 $6,000
August 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,500
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$6,500
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$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
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$6,000
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$5,000
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$5,000
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$5,000
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30
 $5,000
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Lovely Updated Cape Style Home, Beautifully Landscaped Yard, Deck & Patio with Multiple Seating Areas & Outdoor Dining

Nestled in a peaceful lane in Edgartown's desirable Dodger’s Hole Area, this charming Cape-style home offers a central location with easy access to Edgartown, Oak Bluffs, Vineyard Haven, and several...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,500 - $6,500
June 2025
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July 2025
SuMoTuWeThFrSaWeek
 1
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$3,500
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$3,500
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 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$4,000
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$6,500
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$6,500
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$6,500
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$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
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3
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$4,500
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$3,500
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$3,000
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$3,000
28
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 $2,500
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner reduced rates for available weeks in July - see calendar for adjusted rates

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Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,550 - $6,470
June 2025
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July 2025
SuMoTuWeThFrSaWeek
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31
 $5,200
August 2025
SuMoTuWeThFrSaWeek
 1
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$5,200
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$5,800
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$5,800
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$5,800
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$5,500
31
 
September 2025
SuMoTuWeThFrSaWeek
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$4,550
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29
30
 
Clean Fee: 
$525 per week
Tax: State & Local: 
11.7
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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: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $6,200
June 2025
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July 2025
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 1
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3
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$5,500
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$5,500
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31
 $5,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,900
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$6,000
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$6,000
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$6,000
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$5,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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$4,000
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$2,200
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$2,200
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$2,200
28
29
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 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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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: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,800 - $6,100
June 2025
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July 2025
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 1
2
3
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$4,300
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$4,300
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31
 $4,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,600
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$4,800
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$4,800
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$4,600
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29
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$3,600
31
 $3,300
September 2025
SuMoTuWeThFrSaWeek
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$3,300
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$3,300
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$2,800
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$2,800
28
29
30
 
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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Menemsha

Magical Menemsha Cottage with water views of the Elizabeth Islands and harbor. The wooded property encompasses 3 private acres and is within walking distance to the village of Menemsha and...Read more

Location: 
Chilmark
Sleeps: 
7
Bedrooms: 
3
Baths: 
1
Price Range:
$3,520 - $6,030
June 2025
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July 2025
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$7,000
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$7,000
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31
 $8,220
August 2025
SuMoTuWeThFrSaWeek
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2
$8,220
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$8,220
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$8,220
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$8,220
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$8,220
31
 $6,030
September 2025
SuMoTuWeThFrSaWeek
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$6,030
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$6,030
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$6,030
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$6,030
28
29
30
 $4,050
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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Menemsha Waterfront, Magnificent Views and Private Location, WiFi

This quintessential Chilmark cottage/home has been impeccably maintained,  The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap-around deck.  Enjoy spectacular water views...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $6,000
June 2025
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July 2025
SuMoTuWeThFrSaWeek
 1
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3
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$8,000
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$8,000
27
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31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
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$8,000
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$8,000
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$8,000
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$7,500
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25
26
27
28
29
30
$8,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
$6,000
21
22
23
24
25
26
27
$6,000
28
29
30
 $4,000
Clean Fee: 
$375 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis, Bose Soundock II
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $6,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$6,300
20
21
22
23
24
25
26
$6,300
27
28
29
30
31
 $6,300
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,300
3
4
5
6
7
8
9
$7,200
10
11
12
13
14
15
16
$7,200
17
18
19
20
21
22
23
$7,200
24
25
26
27
28
29
30
$6,000
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$6,000
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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Oak Bluffs 4 Bedroom Home, Walk to Town & Beach!

10-minute walk to Oak Bluffs center and beach area from this lovely modern vacation home.  Enjoy all that the summer community of Oak Bluffs has to offer with quaint shops,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$540 - $6,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$5,250
20
21
22
23
24
25
26
$5,250
27
28
29
30
31
 $5,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,250
3
4
5
6
7
8
9
$6,000
10
11
12
13
14
15
16
$6,000
17
18
19
20
21
22
23
$6,000
24
25
26
27
28
29
30
$5,750
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,200
14
15
16
17
18
19
20
$4,200
21
22
23
24
25
26
27
$4,200
28
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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KATAMA AREA, SET ON PRIVATE ACREAGE, SHORT DRIVE TO SOUTH BEACH AND EDGARTOWN VILLAGE CENTER

Extended family will enjoy the comfort and private setting of this large 5 bedroom home in the Katama area of Edgartown.   Spacious for extended family, the kitchen with custom cabinetry and...Read more

Location: 
Katama
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$2,400 - $6,000
June 2025
SuMoTuWeThFrSa
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,200
27
28
29
30
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,500
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,000
31
 $5,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
$2,900
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

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