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 Upscale Contemporary Home, Designer Details Throughout, 4 Bedrooms, 4.5 Baths, Muliple Living Areas

Discover this stunning tri-level vacation home nestled in a peaceful community just on the outskirts of Oak Bluffs and minutes away from Oak Bluffs center, Edgartown Village, downtown Vineyard Haven, and several...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
4
Baths: 
4
Price Range:
$7,500 - $7,800
June 2025
SuMoTuWeThFrSaWeek
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$7,500
29
30
 $7,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,800
6
7
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12
$7,800
13
14
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18
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$7,800
20
21
22
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26
27
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29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
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$8,000
3
4
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6
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8
9
$8,300
10
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$8,300
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$8,300
24
25
26
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29
30
$7,500
31
 
September 2025
SuMoTuWeThFrSa
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29
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Clean Fee: 
$750 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:
$5,700 - $7,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,300
8
9
10
11
12
13
14
$6,300
15
16
17
18
19
20
21
$6,300
22
23
24
25
26
27
28
$6,300
29
30
 $6,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,400
6
7
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11
12
$6,400
13
14
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18
19
$6,400
20
21
22
23
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25
26
$6,400
27
28
29
30
31
 $7,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,200
3
4
5
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$7,200
10
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$7,200
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18
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$7,200
24
25
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29
30
$7,200
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
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$5,700
7
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25
26
27
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29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

This home books Friday to Friday June-September

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LONGK

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Property Details
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:
$5,000 - $7,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
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$5,000
22
23
24
25
26
27
28
$5,000
29
30
 $6,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,300
6
7
8
9
10
11
12
$6,300
13
14
15
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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
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13
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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
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$6,000
7
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$6,000
14
15
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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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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:
$5,550 - $7,150
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,550
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,500
22
23
24
25
26
27
28
$6,500
29
30
 $7,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,150
6
7
8
9
10
11
12
$7,150
13
14
15
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18
19
$7,150
20
21
22
23
24
25
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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9
$7,150
10
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$7,150
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18
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$7,150
24
25
26
27
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29
30
$7,150
31
 $7,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
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6
$7,000
7
8
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10
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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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KNOXA

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Property Details
Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,150 - $7,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,150
8
9
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14
$3,150
15
16
17
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21
$3,150
22
23
24
25
26
27
28
$3,150
29
30
 $3,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,600
6
7
8
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10
11
12
$3,600
13
14
15
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19
$3,600
20
21
22
23
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25
26
$3,600
27
28
29
30
31
 $4,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,900
3
4
5
6
7
8
9
$7,000
10
11
12
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16
$7,000
17
18
19
20
21
22
23
$4,200
24
25
26
27
28
29
30
$3,800
31
 $3,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,600
7
8
9
10
11
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13
$3,600
14
15
16
17
18
19
20
$3,600
21
22
23
24
25
26
27
$3,600
28
29
30
 $3,150
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

Ferry Tickets Available for week of 7/6 - please inquire

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GUCOB

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Property Details
Spacious Home with Heated Pool, Pool Bar with TV, Patio Surround, Deck Overlooking the Pool & Yard, Centrally Located

Spacious home with private heated pool & hot tub, tucked away in a quiet neighborhood, centrally located providing easy access to beaches and towns.  The pool, patio area, deck, & pool bar...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$6,820 - $6,820
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,820
8
9
10
11
12
13
14
$6,820
15
16
17
18
19
20
21
$6,820
22
23
24
25
26
27
28
$6,820
29
30
 $10,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
31
 $10,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$10,000
3
4
5
6
7
8
9
$10,000
10
11
12
13
14
15
16
$10,000
17
18
19
20
21
22
23
$10,000
24
25
26
27
28
29
30
$10,000
31
 $6,820
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,820
7
8
9
10
11
12
13
$6,820
14
15
16
17
18
19
20
$6,820
21
22
23
24
25
26
27
$6,820
28
29
30
 $6,820
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Pool Heated to 80 degrees included in the rental rate, July & August

Pool Heated to 80 degrees, June & September, additional 350 per week surcharge

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FISHJ

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Property Details
Stylish Contemporary Vacation Home situated in Meadow View Farms, Open Light Filled Design, Expansive Private Deck

Come and enjoy this light-filled, beautifully maintained, three-level contemporary home complete with gardens, landscaped yard, and a children’s backyard playground.  

The main level features an open kitchen, dining, and TV/living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $6,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,000
8
9
10
11
12
13
14
$4,500
15
16
17
18
19
20
21
$4,500
22
23
24
25
26
27
28
$4,500
29
30
 $6,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,800
6
7
8
9
10
11
12
$6,800
13
14
15
16
17
18
19
$6,800
20
21
22
23
24
25
26
$6,800
27
28
29
30
31
 
August 2025
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
$6,800
31
 $3,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,900
7
8
9
10
11
12
13
$3,900
14
15
16
17
18
19
20
$3,900
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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ARMSA

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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:
$3,500 - $6,600
June 2025
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
$5,500
22
23
24
25
26
27
28
$5,500
29
30
 
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$6,600
20
21
22
23
24
25
26
$6,600
27
28
29
30
31
 
August 2025
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
31
 $5,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$5,500
28
29
30
 $3,500
Clean Fee: 
$300 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 - $6,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,500
8
9
10
11
12
13
14
$3,500
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$3,900
29
30
 $6,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
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
31
 $6,400
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,400
3
4
5
6
7
8
9
$6,600
10
11
12
13
14
15
16
$6,600
17
18
19
20
21
22
23
$6,600
24
25
26
27
28
29
30
$6,600
31
 $6,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,600
7
8
9
10
11
12
13
$4,100
14
15
16
17
18
19
20
$4,100
21
22
23
24
25
26
27
$4,100
28
29
30
 $2,600
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7

Rate reduced for week 7/11-7/18 - see calendar for adjusted rates

 

Owner books Fri to Fri July & August weeks!

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WESTW

(0)Inquire/Share
Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

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

(0)Inquire/Share
Property Details
Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

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

(0)Inquire/Share
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 - $6,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,200
8
9
10
11
12
13
14
$4,600
15
16
17
18
19
20
21
$5,100
22
23
24
25
26
27
28
$5,700
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,200
6
7
8
9
10
11
12
$6,100
13
14
15
16
17
18
19
$6,100
20
21
22
23
24
25
26
$6,100
27
28
29
30
31
 $6,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$6,500
3
4
5
6
7
8
9
$6,500
10
11
12
13
14
15
16
$6,900
17
18
19
20
21
22
23
$6,500
24
25
26
27
28
29
30
$6,500
31
 $6,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,500
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$4,700
21
22
23
24
25
26
27
$4,700
28
29
30
 
Clean Fee: 
$390 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BAKE7

(0)Inquire/Share
Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.
Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $6,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,400
8
9
10
11
12
13
14
$4,400
15
16
17
18
19
20
21
$4,900
22
23
24
25
26
27
28
$4,900
29
30
 $6,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
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
$9,000
27
28
29
30
31
 $12,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$12,000
3
4
5
6
7
8
9
$12,000
10
11
12
13
14
15
16
$12,000
17
18
19
20
21
22
23
$12,000
24
25
26
27
28
29
30
$8,500
31
 $5,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,700
7
8
9
10
11
12
13
$5,700
14
15
16
17
18
19
20
$5,700
21
22
23
24
25
26
27
$5,700
28
29
30
 $5,600
Clean Fee: 
$400 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 2025
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
 $8,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
31
 $7,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,000
3
4
5
6
7
8
9
$7,500
10
11
12
13
14
15
16
$7,500
17
18
19
20
21
22
23
$8,500
24
25
26
27
28
29
30
$6,500
31
 
September 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
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CORAG

(0)Inquire/Share
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 - $6,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
 $7,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$8,000
27
28
29
30
31
 $8,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$8,000
3
4
5
6
7
8
9
10
11
12
13
14
15
16
$8,000
17
18
19
20
21
22
23
$8,000
24
25
26
27
28
29
30
$6,200
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: 
$400 per week
Tax: State & Local: 
11.7

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