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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Located in the Heart of Oak Bluffs, 5 Minute Walk to OB Center and 2 Blocks to the Beach
Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
2
Price Range:
$10 - $4,600
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,900
8
9
10
11
12
13
14
$3,900
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$4,200
29
30
 $4,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,600
6
7
8
9
10
11
12
$4,600
13
14
15
16
17
18
19
$4,600
20
21
22
23
24
25
26
$4,600
27
28
29
30
31
 $4,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,600
3
4
5
6
7
8
9
$4,600
10
11
12
13
14
15
16
$4,600
17
18
19
20
21
22
23
$4,600
24
25
26
27
28
29
30
$4,600
31
 $4,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,600
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,000
28
29
30
 
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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WILCM

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Property Details
Hidden Cove, Association Tennis Courts, 3 Bedrooms, 2.5 Baths, Screened Porch and Deck

Nestled in the charming Hidden Cove community, this adorable contemporary home resides on a tranquil street within walking distance of the association's tennis courts. Its central location places it just...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,500
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
$3,800
29
30
 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $5,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$5,000
3
4
5
6
7
8
9
$5,000
10
11
12
13
14
15
16
$5,000
17
18
19
20
21
22
23
$5,000
24
25
26
27
28
29
30
$4,500
31
 $3,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,800
7
8
9
10
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12
13
$3,800
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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PETEO

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Property Details
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:
$10 - $4,500
June 2025
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
$4,500
22
23
24
25
26
27
28
$5,600
29
30
 $6,200
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,200
6
7
8
9
10
11
12
$6,200
13
14
15
16
17
18
19
$6,200
20
21
22
23
24
25
26
$6,700
27
28
29
30
31
 $7,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$7,200
3
4
5
6
7
8
9
$7,600
10
11
12
13
14
15
16
$7,600
17
18
19
20
21
22
23
$7,600
24
25
26
27
28
29
30
$6,500
31
 $3,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,900
7
8
9
10
11
12
13
$3,400
14
15
16
17
18
19
20
$3,400
21
22
23
24
25
26
27
$3,400
28
29
30
 
Clean Fee: 
$575 per week
Tax: State & Local: 
11.7
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KEANM

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Property Details
Lovely Oak Bluffs Home, 3 Bedrooms, 2.5 Baths, Sleeps 7. Set just on the Outskirts of Oak Bluffs Center

Lovely 3 bedroom, 2.5 bath home that sleeps 7. This sweet home is bordered by a large yard and is located just on the outskirts of Oak Bluffs. The patio...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,950
8
9
10
11
12
13
14
$2,950
15
16
17
18
19
20
21
$2,950
22
23
24
25
26
27
28
$2,950
29
30
 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$4,000
31
 $4,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$3,200
14
15
16
17
18
19
20
$3,200
21
22
23
24
25
26
27
$3,000
28
29
30
 $2,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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CLARO

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Property Details
New Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch and Farmers Porch, Bike or Walk to Oak Bluffs Center.

Situated just on the outskirts of Oak Bluffs, this lovely new vacation home offers renters modern styling with multiple living spaces and all the conveniences renters look for in a vacation...Read more

Location: 
Oak Bluffs
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,300
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,000
8
9
10
11
12
13
14
$3,000
15
16
17
18
19
20
21
$3,300
22
23
24
25
26
27
28
$3,950
29
30
 $4,300
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,300
6
7
8
9
10
11
12
$4,300
13
14
15
16
17
18
19
$4,300
20
21
22
23
24
25
26
$4,300
27
28
29
30
31
 $4,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,600
3
4
5
6
7
8
9
$4,800
10
11
12
13
14
15
16
$4,800
17
18
19
20
21
22
23
$4,600
24
25
26
27
28
29
30
$3,600
31
 $3,300
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,300
7
8
9
10
11
12
13
$3,300
14
15
16
17
18
19
20
$2,800
21
22
23
24
25
26
27
$2,800
28
29
30
 
Clean Fee: 
$425 per week
Tax: State & Local: 
11.7
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DONOP

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Property Details
Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi

Centrally located in the Hidden Cove community of homes on the outskirts of Oak Bluffs. Lovely area to bike, walk, or play tennis at the association courts. 

The main level features an...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $4,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,400
8
9
10
11
12
13
14
$3,050
15
16
17
18
19
20
21
$3,050
22
23
24
25
26
27
28
$3,200
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,200
20
21
22
23
24
25
26
$4,200
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$3,400
31
 $2,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,600
7
8
9
10
11
12
13
$2,600
14
15
16
17
18
19
20
$2,600
21
22
23
24
25
26
27
$2,600
28
29
30
 $2,600
Clean Fee: 
$375 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:
$10 - $4,200
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,150
8
9
10
11
12
13
14
$3,150
15
16
17
18
19
20
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
9
10
11
12
$3,600
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
31
 $4,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,200
3
4
5
6
7
8
9
$7,000
10
11
12
13
14
15
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
12
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
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PETEV

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Property Details
Lovely Waterfront Home, Oak Bluffs, Gorgeous Water Views, Association Tennis Courts, AC, Wi-fi, Bike Paths Nearby

Note: Pricing for this waterfront home takes into account that this is an older-style home. Please note that baths and kitchen have not been updated

MVVR Exclusive! Spacious, traditional waterfront Cape Cod style home...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$10 - $4,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,600
8
9
10
11
12
13
14
$3,600
15
16
17
18
19
20
21
$3,600
22
23
24
25
26
27
28
$3,600
29
30
 $4,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,100
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,100
27
28
29
30
31
 $4,100
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,100
3
4
5
6
7
8
9
$4,100
10
11
12
13
14
15
16
$4,100
17
18
19
20
21
22
23
$4,100
24
25
26
27
28
29
30
$3,910
31
 $3,660
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,660
7
8
9
10
11
12
13
$3,660
14
15
16
17
18
19
20
$3,660
21
22
23
24
25
26
27
$2,460
28
29
30
 $2,460
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MAHAB

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Property Details
Sweet Updated 3 Bedroom Home, Nicely Tucked in Lightly Wooded Area, Central Location, Beaches and Towns just a short Drive!

Lovely reverse contemporary home with a large deck, outdoor dining, and grill area. The upper level of this home features an open kitchen, living, and dining area stylishly furnished.  Nicely equipped kitchen...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $4,000
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
$3,500
22
23
24
25
26
27
28
$3,500
29
30
 $4,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$3,500
31
 $3,500
September 2025
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
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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CAH48

(0)Inquire/Share
Property Details
Classic Lovely Vineyard Cottage, Pristine Condition, Approximately 1.5 Miles to Town and Beaches. Mature Landscaped Yard, Spacious Deck

The Perfect Cozy Cottage, is pristinely maintained and situated in a quiet neighborhood just on the outskirts of Oak Bluffs.  This spacious 2 bedroom, 2 bath home sleeps 4. The...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$10 - $4,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,900
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$4,000
31
 $2,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 
Clean Fee: 
$300, additional may apply multiple week rentals
Tax: State & Local: 
11.7
Add Favorite
 
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SACHE

(0)Inquire/Share
Property Details
Waterview Farms, Water view

Lovely contemporary home in one of the island's premier community settings, Waterview Farms. Close to Farm Neck Golf Course and tennis and a short distance to town and beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $3,800
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
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,500
27
28
29
30
31
 $3,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,500
3
4
5
6
7
8
9
$3,800
10
11
12
13
14
15
16
$3,800
17
18
19
20
21
22
23
$3,800
24
25
26
27
28
29
30
$3,800
31
 $3,500
September 2025
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
$3,500
21
22
23
24
25
26
27
$3,500
28
29
30
 $3,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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KLEIB

(0)Inquire/Share
Property Details
Lagoon Waterfront & Beachfront, Spectacular Water views, Room A/C, WIFI

Adorable waterfront & beachfront cottage.   Immaculately maintained, lots of summer charm, fantastic views of the Vineyard Sound and Lagoon from the large patio area. Stairs lead directly to a...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $3,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,760
8
9
10
11
12
13
14
$3,040
15
16
17
18
19
20
21
$3,050
22
23
24
25
26
27
28
$3,400
29
30
 $3,400
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,400
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
31
 $4,020
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,020
3
4
5
6
7
8
9
$4,100
10
11
12
13
14
15
16
$4,100
17
18
19
20
21
22
23
$3,920
24
25
26
27
28
29
30
$3,720
31
 $2,770
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,770
7
8
9
10
11
12
13
$2,540
14
15
16
17
18
19
20
$2,390
21
22
23
24
25
26
27
$2,300
28
29
30
 $2,190
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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KOEOB

(0)Inquire/Share
Property Details
Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$10 - $3,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,500
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,700
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
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
31
 $3,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,800
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$3,500
31
 $3,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,500
28
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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LODGJ

(0)Inquire/Share
Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$10 - $3,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$2,900
22
23
24
25
26
27
28
$2,900
29
30
 $3,000
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,000
20
21
22
23
24
25
26
$3,000
27
28
29
30
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$3,000
31
 $2,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,900
7
8
9
10
11
12
13
$2,900
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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GOLLB

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Property Details
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$10 - $2,850
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$2,250
15
16
17
18
19
20
21
$2,650
22
23
24
25
26
27
28
$2,850
29
30
 $3,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,150
6
7
8
9
10
11
12
$3,150
13
14
15
16
17
18
19
$3,150
20
21
22
23
24
25
26
$3,150
27
28
29
30
31
 $3,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,250
3
4
5
6
7
8
9
$3,250
10
11
12
13
14
15
16
$3,250
17
18
19
20
21
22
23
$3,250
24
25
26
27
28
29
30
$2,850
31
 $1,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,950
7
8
9
10
11
12
13
$1,950
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $1,850
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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