Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Beautiful Custom Built Home Overlooking Little Duarte Pond, Beautifully Landscaped

Outstanding vacation home, centrally located to all three down-island town centers and multiple public beaches. This lovely home in a serene setting overlooks the picturesque Little Duarte Pond in the Iron Hill...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
5
Price Range:
$4,000 - $7,500
June 2026
SuMoTuWeThFrSaWeek
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$4,000
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$4,000
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$4,000
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$5,600
28
29
30
 $7,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
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$7,500
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$8,500
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September 2026
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Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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TRAVM

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Property Details
Updated East Chop Area Summer Retreat, Great Proximity to Town Center and Beaches, Cottage Styling with All the Modern Amenities, Central A/C. Covered Porch and Open Patio Areas.

Visitors will enjoy this delightful &  comfortable 4 bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. 

Relax in the breeze with your morning coffee on the front...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,350 - $7,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
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14
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29
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 $5,350
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,350
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$5,350
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$5,350
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$5,350
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27
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30
31
 $7,000
August 2026
SuMoTuWeThFrSaWeek
 1
$7,000
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$7,000
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$7,200
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$7,500
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30
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September 2026
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Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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HAZAM

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Property Details
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:
$3,700 - $7,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,400
7
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$5,600
14
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$6,500
21
22
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27
$7,000
28
29
30
 $7,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
6
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$7,000
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$7,000
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$7,000
26
27
28
29
30
31
 $7,500
August 2026
SuMoTuWeThFrSaWeek
 1
$7,500
2
3
4
5
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$8,300
9
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$8,700
16
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$8,700
23
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$7,000
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
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$5,200
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$4,200
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$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500
Tax: State & Local: 
11.7
Add Favorite
 
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JOHNL

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Property Details
"Endless Summer Vacation" Stylish, Newly Updated 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
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5
6
$4,000
7
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$4,000
14
15
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$4,000
21
22
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27
$4,000
28
29
30
 $5,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,000
5
6
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$5,000
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$5,000
19
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21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
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$7,500
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$7,500
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$7,500
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$7,500
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
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2
3
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$5,000
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$5,000
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$5,000
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$5,000
27
28
29
30
 $5,000
Clean Fee: 
$450 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
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6
$6,800
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$6,800
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$6,800
21
22
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$6,800
28
29
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 $6,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
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$6,900
5
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$6,900
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$6,900
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$6,900
26
27
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30
31
 $6,900
August 2026
SuMoTuWeThFrSaWeek
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$6,900
2
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$7,900
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$7,900
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$7,900
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$7,900
30
31
 $7,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
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5
$7,200
6
7
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14
15
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20
21
22
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24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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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
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13
$3,500
14
15
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$3,900
21
22
23
24
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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
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15
$7,200
16
17
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19
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21
22
$7,200
23
24
25
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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
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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
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14
15
$9,000
16
17
18
19
20
21
22
$8,500
23
24
25
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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
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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
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18
$7,150
19
20
21
22
23
24
25
$7,150
26
27
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30
31
 $7,150
August 2026
SuMoTuWeThFrSaWeek
 1
$7,150
2
3
4
5
6
7
8
$7,150
9
10
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15
$7,150
16
17
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21
22
$7,150
23
24
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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
Add Favorite
 
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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
9
10
11
12
13
$4,600
14
15
16
17
18
19
20
$5,100
21
22
23
24
25
26
27
$5,700
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
 $6,600
August 2026
SuMoTuWeThFrSaWeek
 1
$6,600
2
3
4
5
6
7
8
$7,000
9
10
11
12
13
14
15
$7,000
16
17
18
19
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
Add Favorite
 
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THOMS

(0)Inquire/Share
Property Details
New Modern Farmhouse Design, Great Location!, Wraparound Farmers Porch, Deck Area.

Beautiful new 4 bedroom home, 3.5 bath sleeps 8.  Ideally located just 2 miles from the center of Oak Bluffs and just minutes by car to the towns of Vineyard Haven and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $6,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
11
12
13
$3,800
14
15
16
17
18
19
20
$3,800
21
22
23
24
25
26
27
$3,800
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
 $6,900
August 2026
SuMoTuWeThFrSaWeek
 1
$6,900
2
3
4
5
6
7
8
$6,800
9
10
11
12
13
14
15
$6,800
16
17
18
19
20
21
22
$6,800
23
24
25
26
27
28
29
$6,800
30
31
 $6,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,900
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
 $3,800
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ARMSA

(0)Inquire/Share
Property Details
Cozy Newly updated Seashore Cottage, East Chop Highlands Area, Farmers Porch and Deck

If you are looking for an immaculate, charming, cottage-style, yet modern home close to Oak Bluffs center, look no further. This recently updated 3 bedroom, 2 bath home features sunny open...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,600 - $6,700
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,600
7
8
9
10
11
12
13
$5,600
14
15
16
17
18
19
20
$5,600
21
22
23
24
25
26
27
$5,600
28
29
30
 $6,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,700
5
6
7
8
9
10
11
$6,700
12
13
14
15
16
17
18
$6,700
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
31
 $6,700
August 2026
SuMoTuWeThFrSaWeek
 1
$6,700
2
3
4
5
6
7
8
$6,700
9
10
11
12
13
14
15
$6,700
16
17
18
19
20
21
22
$6,700
23
24
25
26
27
28
29
$6,700
30
31
 $5,600
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,600
6
7
8
9
10
11
12
$5,600
13
14
15
16
17
18
19
$5,600
20
21
22
23
24
25
26
$5,600
27
28
29
30
 $5,600
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BOOND

(0)Inquire/Share
Property Details
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:
$4,000 - $6,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
 $5,200
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,200
5
6
7
8
9
10
11
$5,200
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,000
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
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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VANA2

(0)Inquire/Share
Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $6,500
June 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
 
July 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
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$6,500
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: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BARNJ

(0)Inquire/Share
Property Details
Chic, Meticulously Maintained Cape Style Home, 3 bedrooms, 3 Baths, Sleeps 6, Walk to Oak Bluffs Town Center and Beaches, Tucked on a Large Beautifully Landscaped Lot

Nestled in a beautifully landscaped lot in a serene and private neighborhood, this meticulously maintained cottage in Oak Bluffs offers a perfect retreat for rental guests. With chic luxury amenities, it's...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,750 - $6,350
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,750
7
8
9
10
11
12
13
$3,750
14
15
16
17
18
19
20
$4,350
21
22
23
24
25
26
27
$4,600
28
29
30
 $5,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
14
15
16
17
18
$5,600
19
20
21
22
23
24
25
$5,600
26
27
28
29
30
31
 $5,600
August 2026
SuMoTuWeThFrSaWeek
 1
$5,600
2
3
4
5
6
7
8
$6,850
9
10
11
12
13
14
15
$6,850
16
17
18
19
20
21
22
$6,850
23
24
25
26
27
28
29
$6,350
30
31
 $3,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,750
6
7
8
9
10
11
12
$3,750
13
14
15
16
17
18
19
$3,750
20
21
22
23
24
25
26
$3,750
27
28
29
30
 $3,750
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CENCR

(0)Inquire/Share
Property Details
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: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $6,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
 $5,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,800
5
6
7
8
9
10
11
$5,800
12
13
14
15
16
17
18
$6,200
19
20
21
22
23
24
25
$6,200
26
27
28
29
30
31
 $6,200
August 2026
SuMoTuWeThFrSaWeek
 1
$6,200
2
3
4
5
6
7
8
$10,500
9
10
11
12
13
14
15
$11,800
16
17
18
19
20
21
22
$11,800
23
24
25
26
27
28
29
$6,200
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

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