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The Retreat at Towanticut Where Coastal Elegance Meets Island Serenity, 3 Bedrooms, 2 Baths, Landscaped Yard, Deck Dining Area

Welcome to The Retreat at Towanticut— a chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $7,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,400
7
8
9
10
11
12
13
$5,600
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$7,000
28
29
30
 $7,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
31
 $7,500
August 2026
SuMoTuWeThFrSaWeek
 1
$7,500
2
3
4
5
6
7
8
$8,300
9
10
11
12
13
14
15
$8,700
16
17
18
19
20
21
22
$8,700
23
24
25
26
27
28
29
$7,000
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,200
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500
Tax: State & Local: 
11.7
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JOHNL

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Property Details
"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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$7,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
 $5,000
Clean Fee: 
$450 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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THOMR

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Property Details
High St House, Ideal In-town Location, Beautiful 4 Bedroom, 4 .5 Bath Home, Walk to Edgartown Village Center, 5 Minute Drive to South Beach

Beautiful village area colonial with contemporary designer interior and luxury amenities. For those who love an in-town location with easy walking distance to Main St, this home provides the perfect location. South...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$7,430 - $7,430
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$12,400
7
8
9
10
11
12
13
$13,600
14
15
16
17
18
19
20
$14,500
21
22
23
24
25
26
27
$16,650
28
29
30
 $16,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,650
5
6
7
8
9
10
11
$17,250
12
13
14
15
16
17
18
$17,250
19
20
21
22
23
24
25
$17,250
26
27
28
29
30
31
 $17,850
August 2026
SuMoTuWeThFrSaWeek
 1
$17,850
2
3
4
5
6
7
8
$17,850
9
10
11
12
13
14
15
$17,850
16
17
18
19
20
21
22
$15,130
23
24
25
26
27
28
29
$13,900
30
31
 $12,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,700
6
7
8
9
10
11
12
$11,650
13
14
15
16
17
18
19
$10,300
20
21
22
23
24
25
26
$9,100
27
28
29
30
 $8,150
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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FERGN

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Property Details
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:
$7,400 - $7,400
June 2026
SuMoTuWeThFrSaWeek
 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
 $7,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,400
5
6
7
8
9
10
11
$7,400
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$6,900
23
24
25
26
27
28
29
$6,900
30
31
 
September 2026
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
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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ELOUA

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Property Details
Lovely updated Home , Village Area Edgartown, 7 minute Walk to Main St. Bike Paths at end of Street.

Minutes from downtown Edgartown's shops & restaurants, this cape style home features open concept living, air conditioning, a mini-split in the main living area, window units in all but 1st level...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,850 - $7,350
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,650
7
8
9
10
11
12
13
$6,650
14
15
16
17
18
19
20
$6,650
21
22
23
24
25
26
27
$6,650
28
29
30
 $7,350
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,350
5
6
7
8
9
10
11
$7,350
12
13
14
15
16
17
18
$7,350
19
20
21
22
23
24
25
$7,350
26
27
28
29
30
31
 $7,350
August 2026
SuMoTuWeThFrSaWeek
 1
$7,350
2
3
4
5
6
7
8
$8,050
9
10
11
12
13
14
15
$8,050
16
17
18
19
20
21
22
$8,050
23
24
25
26
27
28
29
$8,050
30
31
 $6,650
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,650
6
7
8
9
10
11
12
$6,650
13
14
15
16
17
18
19
$6,650
20
21
22
23
24
25
26
$6,650
27
28
29
30
 $6,650
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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WEINS

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Property Details
Charming and Pristine Hilltop Restored Farm House, Water views, Spectacular Sunsets, Set on Large Private Acreage

Hilltop House is located on one of the highest points on the Island displaying broad views across the rolling hills to beautiful water views beyond. Acres of undisturbed privacy and a...Read more

Location: 
Aquinnah
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$6,800 - $7,300
June 2026
SuMoTuWeThFrSaWeek
 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
 $7,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,300
5
6
7
8
9
10
11
$7,300
12
13
14
15
16
17
18
$7,300
19
20
21
22
23
24
25
$7,300
26
27
28
29
30
31
 $7,300
August 2026
SuMoTuWeThFrSaWeek
 1
$7,300
2
3
4
5
6
7
8
$7,300
9
10
11
12
13
14
15
$7,300
16
17
18
19
20
21
22
$7,300
23
24
25
26
27
28
29
$7,300
30
31
 $6,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,800
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
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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WHARG

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Property Details
Lovely Home in a quiet Neighborhood. Walk to Town Center and Inkwell Beach, Large Private Deck, Room AC

Spacious sun-filled contemporary home located on a quiet private street, a 10-minute walk to town center, Inkwell Beach, and the harborfront.

The first level features a spacious kitchen with stainless steel...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$6,800 - $7,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,800
7
8
9
10
11
12
13
$6,800
14
15
16
17
18
19
20
$6,800
21
22
23
24
25
26
27
$6,800
28
29
30
 $6,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,900
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,900
19
20
21
22
23
24
25
$6,900
26
27
28
29
30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
6
7
8
$7,900
9
10
11
12
13
14
15
$7,900
16
17
18
19
20
21
22
$7,900
23
24
25
26
27
28
29
$7,900
30
31
 $7,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,200
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
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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LONGK

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Property Details
Bayes Hill Beauty - Stunning Landscaping, Privately Situated Deck & Patio Association Tennis

Note: Caretaker lives in apartment above the garage. Renter's privacy respected.  Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,000 - $7,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
 $6,300
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,300
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$6,300
19
20
21
22
23
24
25
$6,300
26
27
28
29
30
31
 $6,300
August 2026
SuMoTuWeThFrSaWeek
 1
$6,300
2
3
4
5
6
7
8
$7,200
9
10
11
12
13
14
15
$7,200
16
17
18
19
20
21
22
$7,200
23
24
25
26
27
28
29
$6,000
30
31
 $6,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
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
Add Favorite
 
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TERSM

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Property Details
Modern, Newly Renovated, Architecturally Significant Beach Cottage Design. Close to Town and Beaches, Tucked in the Lovely Community of Summer Homes, Waterview Farms!

Gorgeous all newly renovated and newly furnished mid-century beach cottage, now a modern vacation oasis designed by the prominent interior design firm, - Tersigni Palachek. This eloquent, yet beachy home offers...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,600 - $7,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,900
21
22
23
24
25
26
27
$3,900
28
29
30
 $6,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,400
5
6
7
8
9
10
11
$6,400
12
13
14
15
16
17
18
$6,400
19
20
21
22
23
24
25
$6,400
26
27
28
29
30
31
 $6,400
August 2026
SuMoTuWeThFrSaWeek
 1
$6,400
2
3
4
5
6
7
8
$7,200
9
10
11
12
13
14
15
$7,200
16
17
18
19
20
21
22
$7,200
23
24
25
26
27
28
29
$7,200
30
31
 $7,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,200
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
 $2,700
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Owner books Fri to Fri July & August weeks!

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CORAG

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Property Details
Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$1,650 - $7,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,000
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$7,200
21
22
23
24
25
26
27
$7,200
28
29
30
 $7,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,700
5
6
7
8
9
10
11
$7,700
12
13
14
15
16
17
18
$7,700
19
20
21
22
23
24
25
$7,700
26
27
28
29
30
31
 $9,000
August 2026
SuMoTuWeThFrSaWeek
 1
$9,000
2
3
4
5
6
7
8
$9,000
9
10
11
12
13
14
15
$9,000
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$7,500
30
31
 $7,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,200
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BICKE

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Property Details
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 2026
SuMoTuWeThFrSaWeek
 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
 $7,150
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,150
5
6
7
8
9
10
11
$7,150
12
13
14
15
16
17
18
$7,150
19
20
21
22
23
24
25
$7,150
26
27
28
29
30
31
 $7,150
August 2026
SuMoTuWeThFrSaWeek
 1
$7,150
2
3
4
5
6
7
8
$7,150
9
10
11
12
13
14
15
$7,150
16
17
18
19
20
21
22
$7,150
23
24
25
26
27
28
29
$7,150
30
31
 $7,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$6,500
27
28
29
30
 $6,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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QUINJ

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Property Details
Newly Refurbished Contemporary Home, Beautifully Furnished, Privately Situated with Large Yard and Wraparound Farmer’s Porch, Dodger’s Hole Area

A great vacation begins with a great vacation home. This spacious home set on a private, large landscaped lot is sure to please. The summer wrap around porch is the perfect...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,550 - $7,150
June 2026
SuMoTuWeThFrSaWeek
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2
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$6,750
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$6,750
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$6,750
21
22
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27
$6,750
28
29
30
 $6,950
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,950
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6
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$6,950
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$6,950
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20
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25
$6,950
26
27
28
29
30
31
 $7,150
August 2026
SuMoTuWeThFrSaWeek
 1
$7,150
2
3
4
5
6
7
8
$7,150
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10
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$7,150
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17
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21
22
$7,150
23
24
25
26
27
28
29
$7,150
30
31
 $6,550
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$6,550
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7
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$6,550
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$6,550
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21
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26
$6,550
27
28
29
30
 $6,550
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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PE585

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Property Details
Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$4,040 - $7,090
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,530
7
8
9
10
11
12
13
$5,530
14
15
16
17
18
19
20
$5,530
21
22
23
24
25
26
27
$5,530
28
29
30
 $7,090
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,090
5
6
7
8
9
10
11
$7,090
12
13
14
15
16
17
18
$7,090
19
20
21
22
23
24
25
$7,090
26
27
28
29
30
31
 $7,090
August 2026
SuMoTuWeThFrSaWeek
 1
$7,090
2
3
4
5
6
7
8
$7,090
9
10
11
12
13
14
15
$7,090
16
17
18
19
20
21
22
$7,090
23
24
25
26
27
28
29
$6,560
30
31
 $6,040
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,040
6
7
8
9
10
11
12
$5,510
13
14
15
16
17
18
19
$4,990
20
21
22
23
24
25
26
$4,990
27
28
29
30
 $4,460
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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BURBS

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Property Details
Set Just on the ouskirts of Oak Bluffs. Central AC, Screened Porch

Lovely spacious 3+ bedroom, 3.5 bedroom home within a mile from Oak Bluffs center and beach area.  Fully furnished screen porch and shady porch.  This lovely home sleeps families of 8 comfortably.

The main...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$6,000 - $7,000
June 2026
SuMoTuWeThFrSa
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2
3
4
5
6
7
8
9
10
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29
30
 
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
6
7
8
9
10
11
12
13
14
15
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17
18
19
20
21
22
23
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25
$6,000
26
27
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30
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 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
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5
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$7,000
9
10
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13
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15
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$6,500
30
31
 
September 2026
SuMoTuWeThFrSa
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2
3
4
5
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9
10
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12
13
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15
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21
22
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25
26
27
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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LIJOY

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Property Details
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 - $7,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,200
7
8
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12
13
$4,600
14
15
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17
18
19
20
$5,100
21
22
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24
25
26
27
$5,700
28
29
30
 $6,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,400
5
6
7
8
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11
$6,400
12
13
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18
$6,400
19
20
21
22
23
24
25
$6,400
26
27
28
29
30
31
 $6,600
August 2026
SuMoTuWeThFrSaWeek
 1
$6,600
2
3
4
5
6
7
8
$7,000
9
10
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15
$7,000
16
17
18
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20
21
22
$7,000
23
24
25
26
27
28
29
$6,400
30
31
 $6,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,700
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
 $4,700
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7

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