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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Lovely Oak Bluffs Cape, Centrally Located, Newly Updated, 4 Bedrooms, Sleeps 8-9, Large Landscaped Yard
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,000 - $5,800
June 2024
SuMoTuWeThFrSaWeek
 1
$3,500
2
3
4
5
6
7
8
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$3,500
23
24
25
26
27
28
29
$4,500
30
 $5,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$5,800
21
22
23
24
25
26
27
$7,000
28
29
30
31
 $7,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$7,800
4
5
6
7
8
9
10
$7,900
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
$4,900
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
 
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NEWMJ

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Newly update mid-century modern beach house set in the private community of homes surrounding Sengekontacket pond. The cozy summer cottage offers indoor and outdoor living at its best with a...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,450 - $5,800
June 2024
SuMoTuWeThFrSaWeek
 1
$3,670
2
3
4
5
6
7
8
$3,670
9
10
11
12
13
14
15
$3,670
16
17
18
19
20
21
22
$4,720
23
24
25
26
27
28
29
$4,720
30
 $5,800
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,800
7
8
9
10
11
12
13
$5,800
14
15
16
17
18
19
20
$5,800
21
22
23
24
25
26
27
28
29
30
31
 
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
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11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
$5,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,800
8
9
10
11
12
13
14
$3,670
15
16
17
18
19
20
21
$3,670
22
23
24
25
26
27
28
$3,670
29
30
 $3,080
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
 
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ARMSA

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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:
$4,000 - $5,650
June 2024
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,520
9
10
11
12
13
14
15
$4,520
16
17
18
19
20
21
22
23
24
25
26
27
28
29
$5,200
30
 $5,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,200
7
8
9
10
11
12
13
$5,200
14
15
16
17
18
19
20
$5,200
21
22
23
24
25
26
27
$5,200
28
29
30
31
 $5,200
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,200
4
5
6
7
8
9
10
$5,200
11
12
13
14
15
16
17
$5,200
18
19
20
21
22
23
24
$5,200
25
26
27
28
29
30
31
$5,200
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,650
8
9
10
11
12
13
14
$4,520
15
16
17
18
19
20
21
$4,520
22
23
24
25
26
27
28
$4,520
29
30
 $4,520
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
 
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GOLDF

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Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$5,000 - $5,500
June 2024
SuMoTuWeThFrSaWeek
 1
$5,000
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
$9,000
30
 $10,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,000
7
8
9
10
11
12
13
$10,000
14
15
16
17
18
19
20
$10,500
21
22
23
24
25
26
27
$10,500
28
29
30
31
 $11,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
7
8
9
10
$11,000
11
12
13
14
15
16
17
$11,000
18
19
20
21
22
23
24
$11,000
25
26
27
28
29
30
31
$8,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,500
8
9
10
11
12
13
14
$5,500
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Pool Heated to 80 July & August pool included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

 
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ROS22

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Set in the heart of Oak Bluffs and on a quiet residential street, this newly updated tastefully decorated vacation home offers rental guests all the comforts of home inside and out....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$3,000 - $5,500
June 2024
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
 $5,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
31
 $5,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
7
8
9
10
$5,500
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,500
25
26
27
28
29
30
31
$5,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
 
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DAWKN

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Exquisite Designer Home, 10 minute Walk to Oak Bluffs Town Center, Screened Porch, Patio Dining Area, Landscaped Yard, Professionally Decorated, AC

Quietly nestled on a quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$5,050 - $5,400
June 2024
SuMoTuWeThFrSaWeek
 1
$5,100
2
3
4
5
6
7
8
$5,300
9
10
11
12
13
14
15
$5,300
16
17
18
19
20
21
22
$5,300
23
24
25
26
27
28
29
$5,400
30
 $5,400
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,400
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
$5,600
28
29
30
31
 $5,600
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,600
4
5
6
7
8
9
10
$5,600
11
12
13
14
15
16
17
$5,600
18
19
20
21
22
23
24
$5,800
25
26
27
28
29
30
31
$5,100
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,100
8
9
10
11
12
13
14
$5,100
15
16
17
18
19
20
21
$5,100
22
23
24
25
26
27
28
$5,100
29
30
 $5,100
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
 
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BACOL

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Charming Water View Home, Immaculate Beachy Interior, Spacious Shady Deck from which to Enjoy the Views

Located just on the outskirts of Oak Bluffs and overlooking the lagoon, this sweet summer home offers walking access to the lagoon for morning swims and is a great area...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$4,000 - $5,250
June 2024
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,750
30
 $4,850
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,850
7
8
9
10
11
12
13
$4,850
14
15
16
17
18
19
20
$4,850
21
22
23
24
25
26
27
$4,850
28
29
30
31
 $5,250
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,250
4
5
6
7
8
9
10
$5,250
11
12
13
14
15
16
17
$5,250
18
19
20
21
22
23
24
$5,250
25
26
27
28
29
30
31
$5,250
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,750
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$4,000
29
30
 $4,000
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
 
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COWAC

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Lovely Cape, 7 minute walk to town and harbor area, 4 bedrooms, 3 baths, sleeps 7

Lovely 4 bedroom, 3 bath home, pristinely maintained and ideally located just on the outskirts of Oak Bluffs on a quiet street. Short walk to town center and Oak Bluffs town...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$2,500 - $5,250
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,800
30
 $4,600
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,600
7
8
9
10
11
12
13
$4,600
14
15
16
17
18
19
20
$4,600
21
22
23
24
25
26
27
$4,600
28
29
30
31
 $5,250
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,250
4
5
6
7
8
9
10
$5,300
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,300
25
26
27
28
29
30
31
$4,300
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,200
8
9
10
11
12
13
14
$3,200
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,000
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

Ferry ticket available 7/14 to 7/21, Inquire for details, (mv)

 
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PEOTA

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Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks

This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond.  This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,000 - $5,250
June 2024
SuMoTuWeThFrSaWeek
 1
$2,500
2
3
4
5
6
7
8
$3,500
9
10
11
12
13
14
15
$3,500
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,720
30
 $5,250
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,250
7
8
9
10
11
12
13
$4,720
14
15
16
17
18
19
20
$4,720
21
22
23
24
25
26
27
$5,250
28
29
30
31
 $5,770
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,770
4
5
6
7
8
9
10
$5,770
11
12
13
14
15
16
17
$5,770
18
19
20
21
22
23
24
$5,770
25
26
27
28
29
30
31
$4,720
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$2,500
29
30
 $2,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
 
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DENAL

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Charming, 4-bedroom Oak Bluffs Home, pristinely maintained!  The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$3,000 - $5,250
June 2024
SuMoTuWeThFrSaWeek
 1
$4,000
2
3
4
5
6
7
8
$4,000
9
10
11
12
13
14
15
$4,000
16
17
18
19
20
21
22
$4,000
23
24
25
26
27
28
29
$4,000
30
 $5,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$5,000
14
15
16
17
18
19
20
$5,000
21
22
23
24
25
26
27
$5,000
28
29
30
31
 $5,000
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$5,750
11
12
13
14
15
16
17
$5,750
18
19
20
21
22
23
24
$5,250
25
26
27
28
29
30
31
$5,250
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,000
15
16
17
18
19
20
21
$4,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,000
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7

Parking for two cars only, no on-street parking!

 
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TAYLJ

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SPACIOUS LIGHTFILLED 3 BEDROOM, 3 BATH HOME, PRIVATE DECK WITH PATIO DINING, LOCATED IN QUIET COMMUNITY OF HOMES

Enjoy the best of the Island—the serenity of a secluded wooded sanctuary, the convenience, fun and shopping of the 3 Down Island towns (Oak Bluffs, Edgartown and Vineyard Haven), and easy access...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$3,150 - $5,100
June 2024
SuMoTuWeThFrSaWeek
 1
$3,150
2
3
4
5
6
7
8
$3,150
9
10
11
12
13
14
15
$3,300
16
17
18
19
20
21
22
$3,300
23
24
25
26
27
28
29
$4,200
30
 $4,500
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,500
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,800
21
22
23
24
25
26
27
$4,800
28
29
30
31
 $4,900
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,900
4
5
6
7
8
9
10
$5,100
11
12
13
14
15
16
17
18
19
20
21
22
23
24
$5,100
25
26
27
28
29
30
31
$4,900
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,900
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
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29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

This home books Fri to Fri July and August.

 

 
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VANAL

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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 - $5,000
June 2024
SuMoTuWeThFrSaWeek
 1
$3,000
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$4,000
30
 $5,000
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,000
7
8
9
10
11
12
13
$4,500
14
15
16
17
18
19
20
$4,500
21
22
23
24
25
26
27
$4,500
28
29
30
31
 $6,500
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$6,500
4
5
6
7
8
9
10
$6,500
11
12
13
14
15
16
17
$7,500
18
19
20
21
22
23
24
$5,000
25
26
27
28
29
30
31
$4,500
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,500
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $3,000
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
 
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GLOVL

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Lovely Contemporary Home, Quiet Location in Pond View, Private Back Yard, Porch & Deck

Beautifully maintained, family-friendly home.

Lovely 3 Bedroom, 2.5 bath home situated in a quiet enclave of homes known as Pond View and just 2.5 miles to the center of Oak Bluffs....Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,700 - $4,900
June 2024
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
$3,800
30
 $4,700
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,700
7
8
9
10
11
12
13
$4,700
14
15
16
17
18
19
20
$4,700
21
22
23
24
25
26
27
$4,700
28
29
30
31
 $4,900
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,900
4
5
6
7
8
9
10
$4,900
11
12
13
14
15
16
17
$4,900
18
19
20
21
22
23
24
$4,900
25
26
27
28
29
30
31
$4,900
September 2024
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: 
$325 per week
Tax: State & Local: 
11.7
 
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ROBIH

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Seaview Condo Unit, Gorgeous Water Views, In Town Location, Modern updated Interior!

Note: Seavies Condos is a 3-minute walk from the Steamship Authority dock in Oak Bluffs and two blocks from the Island Queen ferry dock. Perfect location if you cannot or...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$1,850 - $4,850
June 2024
SuMoTuWeThFrSaWeek
 1
$1,850
2
3
4
5
6
7
8
$1,940
9
10
11
12
13
14
15
$1,900
16
17
18
19
20
21
22
$2,000
23
24
25
26
27
28
29
$3,300
30
 $3,350
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,350
7
8
9
10
11
12
13
$3,850
14
15
16
17
18
19
20
$3,950
21
22
23
24
25
26
27
$3,950
28
29
30
31
 $4,850
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,850
4
5
6
7
8
9
10
$4,850
11
12
13
14
15
16
17
$4,850
18
19
20
21
22
23
24
$4,850
25
26
27
28
29
30
31
$4,750
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,550
8
9
10
11
12
13
14
$2,350
15
16
17
18
19
20
21
$1,950
22
23
24
25
26
27
28
$1,950
29
30
 $1,950
Clean Fee: 
$230 per week
Tax: State & Local: 
11.7

5 minute walk from Steamship Authority Oak Bluffs dock to the Seaview Condos.  2 blocks from the Island Queen ferry dock.  

 
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DHANM

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Adorable Oak Bluffs Cottage Just Over a Mile to the Village Center and Town Beaches, Porch, Deck, 4 Bedrooms, 2 Baths

Nestled on a quiet street, this recently updated residence boasts delightful indoor and outdoor living areas. The entrance porch offers cozy seating with wicker chairs and a small dining table that...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,300 - $4,800
June 2024
SuMoTuWeThFrSaWeek
 1
$2,300
2
3
4
5
6
7
8
$3,000
9
10
11
12
13
14
15
$3,000
16
17
18
19
20
21
22
$3,000
23
24
25
26
27
28
29
$3,600
30
 $4,200
July 2024
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,200
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
31
 $4,800
August 2024
SuMoTuWeThFrSaWeek
 1
2
3
$4,800
4
5
6
7
8
9
10
$5,500
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,000
25
26
27
28
29
30
31
$4,800
September 2024
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,600
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,000
22
23
24
25
26
27
28
$3,000
29
30
 $2,300
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner will rent beginning and ending on Fridays to accommodate the need for auto ferry tickets or will rent Sat to Sat.  There may be room for other off-weekend bookings, please inquire!

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