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Beautiful Long View Country House, Walk to Lambert's Cove Beach, Central A/C

Extended families will enjoy this lovely 5 bedroom, 3 bath home featuring expanded living space with a first-floor living room and second-floor family/tv room.  Spacious modern kitchen with prep island...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$3,200 - $8,300
June 2025
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July 2025
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$8,000
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$8,000
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 $8,300
August 2025
SuMoTuWeThFrSaWeek
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$8,300
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$8,300
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$8,300
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$8,300
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$8,300
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
28
29
30
 $6,500
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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Mini Retreat with Pool, Private Peaceful Chilmark Location, Lucy Vincent and Menemsha Beaches Nearby.

Impeccably maintained and updated, this adorable summer home is perfect for families looking for luxury features such as quality linens in a quiet location. The 12 by 18-foot spa pool is...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $8,300
June 2025
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July 2025
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$12,000
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$12,000
27
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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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$13,000
31
 $8,300
September 2025
SuMoTuWeThFrSaWeek
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$8,300
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$7,650
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$7,650
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22
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27
$7,650
28
29
30
 $4,800
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner reduced rates for available dates in July & August - see calendar for adjusted rates

 

Pool heated to 82 degrees included in rental rate July & August

Pool heated to 82 degrees, May, June Sept and October additional $150 per week propane surcharge

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Beautiful 3 Bedroom, 3.5 bath Home, Bluestone Patio with Outdoor Dining & Grill , Lovely Landscaped Yard. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$6,000 - $8,200
June 2025
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July 2025
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$8,200
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$8,200
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31
 $8,200
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,200
3
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$12,000
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$12,000
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$12,000
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$8,500
31
 $6,000
September 2025
SuMoTuWeThFrSaWeek
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$6,000
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$6,000
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$6,000
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$6,000
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29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

Please note: This beautiful new home is in the process of being furnished into April. The photos provided are a sampling of the decor. All furnishings and household items will...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,230 - $8,010
June 2025
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July 2025
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$8,010
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$8,010
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31
 $8,010
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,010
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$11,230
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$11,230
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$11,230
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$8,010
31
 $8,010
September 2025
SuMoTuWeThFrSaWeek
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$8,010
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$6,040
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$6,040
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$6,040
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29
30
 $5,230
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

3 night minimum stay required, May, June, September, October,  4 night minimum July to 7/19

 

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Lovely 3 bedroom water view home. Walk to town and Fuller St Beach,

This lovely 3 bedroom home features expansive water views, a beautifully landscaped yard, main living area with walls of glass windows providing beautiful views from within the home. Classic interior design with...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $8,000
June 2025
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July 2025
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$10,000
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$10,000
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 $10,000
August 2025
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,500
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$10,500
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$10,500
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 $10,500
September 2025
SuMoTuWeThFrSaWeek
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$10,500
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$8,000
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$8,000
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$8,000
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 $8,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.

Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$4,400 - $8,000
June 2025
SuMoTuWeThFrSa
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July 2025
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$10,000
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$14,500
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 $14,500
August 2025
SuMoTuWeThFrSaWeek
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$14,500
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$14,500
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$14,500
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$14,500
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$12,500
31
 $10,000
September 2025
SuMoTuWeThFrSaWeek
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$10,000
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$8,000
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$8,000
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$8,000
28
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 $8,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

Parking for 3 cars, no on street parking

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Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,500 - $8,000
June 2025
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July 2025
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$7,000
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$6,000
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 $6,000
August 2025
SuMoTuWeThFrSaWeek
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$6,000
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$8,000
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$8,000
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$8,000
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$6,500
31
 $3,500
September 2025
SuMoTuWeThFrSaWeek
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$3,500
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$3,500
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$3,500
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$3,500
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Note: Owner maintains security camera on front of house

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Outstanding Edgartown Vacation Home, Spacious Coastal Decor Interior, Large Deck, Screened Porch, Just 1.5 miles to the Village Center

Chic Contemporary Farmhouse, just a short distance to Edgartown Village Center, features a quiet and private setting with all-new beach-inspired decor throughout.

The home has an open first-floor layout with the kitchen,...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
4
Price Range:
$3,000 - $7,750
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$7,300
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$7,700
27
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31
 $7,750
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,750
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$7,750
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$7,750
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$7,750
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$5,800
31
 $4,600
September 2025
SuMoTuWeThFrSaWeek
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2
3
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$4,600
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$3,400
14
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$3,400
21
22
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27
$3,000
28
29
30
 $3,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

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

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Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,

Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $7,500
June 2025
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July 2025
SuMoTuWeThFrSaWeek
 1
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3
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$4,500
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$4,500
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31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
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$6,500
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$6,500
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$6,500
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$7,500
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$4,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$4,500
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$3,000
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$3,000
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27
$3,000
28
29
30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Long Point Beach House, All New Primary Suite, Expansive Sun Porch with Living and Dining Areas, Expansive Deck, Private Yard

This Beach-chic Long Point retreat has just undergone an update in most areas with an all-new Primary Bedroom suite and expansive sun porch hosting both living and dining areas and decorated in nautical...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$2,700 - $7,500
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$7,000
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$7,000
27
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31
 $7,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,500
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$7,500
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$7,500
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$7,500
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30
$7,500
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
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2
3
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5
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$4,000
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$4,000
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$4,000
21
22
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25
26
27
28
29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just on the outskirts of Oak Bluffs downtown area this spacious architect-designed custom home offers families and friends an outstanding vacation experience. 

Professionally designed by a noted architect this outstanding...Read more

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

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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"Endless Summer Vacation" Stylish, Newly Update 3 + Bedroom, Sleeps 8, East Chop Area of Oak Bluffs, Deck Living & Dining Area, Screened Porch,
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $7,500
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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8
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$5,000
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21
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24
25
26
$5,000
27
28
29
30
31
 $5,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,500
3
4
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9
$7,500
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11
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$7,500
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$7,500
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25
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27
28
29
30
$5,500
31
 $4,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
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$4,500
7
8
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$4,500
14
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$4,500
21
22
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25
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27
$4,500
28
29
30
 $4,500
Clean Fee: 
$330 per week
Tax: State & Local: 
11.7

Owner will rent off weekend dates to accommodate the need for ferry tickets July weeks. 

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5 minute walk to town center.

Enjoy a view of Vineyard Haven harbor from this 1898 Captain's home. Walk to town, tennis, dining, library, etc... The Captain Henry Stevenson house has been renovated to include a...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$5,900 - $7,400
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$7,400
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31
 
August 2025
SuMoTuWeThFrSaWeek
 1
2
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$7,400
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18
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$7,400
24
25
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27
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30
$7,400
31
 $5,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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$5,900
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Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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burbr-01-entry.jpg
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Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street

Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more

Location: 
Oak Bluffs
Sleeps: 
11
Bedrooms: 
5
Baths: 
3
Price Range:
$7,350 - $7,350
June 2025
SuMoTuWeThFrSa
1
2
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July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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12
13
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15
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19
$7,350
20
21
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23
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25
26
$7,350
27
28
29
30
31
 $7,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,350
3
4
5
6
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8
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$7,350
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$7,350
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18
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23
$7,950
24
25
26
27
28
29
30
$7,950
31
 $7,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,350
7
8
9
10
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12
13
$7,350
14
15
16
17
18
19
20
$7,350
21
22
23
24
25
26
27
$7,350
28
29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Ferry Ticket available for week of 8/24 - please inquire

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East Chop Area, Tri-Level Home with Distant Water views, Located just 1.5 Mi to Oak Bluffs Center

Beautiful summer home with distant water views, located in the desirable East Chop neighborhood.  This 4 bedroom, 3 bath home is located just 1.5 miles from Oak Bluffs Center & Beach. 

The...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $7,150
June 2025
SuMoTuWeThFrSa
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July 2025
SuMoTuWeThFrSaWeek
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2
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$7,150
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26
$7,150
27
28
29
30
31
 $7,150
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,150
3
4
5
6
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$7,150
10
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15
16
$7,150
17
18
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23
$7,150
24
25
26
27
28
29
30
$7,150
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,000
7
8
9
10
11
12
13
$6,500
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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