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Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832


Martha's Vineyard Vacation Rentals in Oak Bluffs








East Chop Summer Cottage With Wraparound Porch!


"Half Mile to Nancy's Restaurant, Close To Downtown, Shopping & Beaches In Residential Neighborhood!"

EAST CHOP LOCATION!! Located across from the historic Baptist Temple Town Park. This charming 1885 Victorian cottage is original to days gone by and a significant part of the Vineyard Highlands. Six bedrooms and two full bathrooms allow for friends and family to visit along with a cozy, bright vi...Read the full description.

JUNE 2025
S M T W T F S Cost
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
$4,700.
29
30
          $4,700.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$4,700.
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
31
    $5,600.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$6,200.
3
4
5
6
7
8
9
$6,200.
10
11
12
13
14
15
16
$6,200.
17
18
19
20
21
22
23
$5,000.
24
25
26
27
28
29
30
$5,000.
31
            $5,000.
SEPTEMBER 2025
S M T W T F S Cost
 
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
        $5,000.
               

Oak Bluffs Waterfront House and Guest House!


"Beautiful Martha's Vineyard Rental! Located Off East Chop Right On The Beach!"

Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
CALL
8
9
10
11
12
13
14
CALL
15
16
17
18
19
20
21
CALL
22
23
24
25
26
27
28
CALL
29
30
          $8,500.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$8,500.
6
7
8
9
10
11
12
$8,500.
13
14
15
16
17
18
19
$8,500.
20
21
22
23
24
25
26
$8,500.
27
28
29
30
31
    $15,000.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$15,000.
3
4
5
6
7
8
9
$15,000.
10
11
12
13
14
15
16
$15,000.
17
18
19
20
21
22
23
$15,000.
24
25
26
27
28
29
30
$15,000.
31
            $15,000.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$15,000.
7
8
9
10
11
12
13
CALL
14
15
16
17
18
19
20
CALL
21
22
23
24
25
26
27
CALL
28
29
30
        CALL
               

Pristine Oak Bluffs Home


"Great location in Oak Bluffs with central air conditioning!"

For 2018, an expansion has been completed to create a new architecturally designed living space with complete central air conditioning system throughout the home. The dining room has seating for 6 with plenty of room for more. The new living room, has picture windows throughout, allowing views of th...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$5,250.
8
9
10
11
12
13
14
$5,250.
15
16
17
18
19
20
21
$5,600.
22
23
24
25
26
27
28
$5,600.
29
30
          $6,800.
               
JULY 2025
S M T W T F S Cost
   
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
    $7,400.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$7,400.
3
4
5
6
7
8
9
$7,400.
10
11
12
13
14
15
16
$7,400.
17
18
19
20
21
22
23
$7,400.
24
25
26
27
28
29
30
$7,400.
31
            $7,400.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
$7,400.
7
8
9
10
11
12
13
$5,425.
14
15
16
17
18
19
20
$5,425.
21
22
23
24
25
26
27
$5,425.
28
29
30
        $5,425.
               

Gracious Oak Bluffs Home


"Elegant with Private Beach and Guest House"

Newly updated in 2024 gracious 5 bedroom house and guest house with brand new screen porch. Private beach access and tennis courts. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a peep of the water. A separate...Read the full description.

JUNE 2025
S M T W T F S Cost
1
2
3
4
5
6
7
$11,000.
8
9
10
11
12
13
14
$11,000.
15
16
17
18
19
20
21
$11,000.
22
23
24
25
26
27
28
$11,000.
29
30
          $13,000.
               
JULY 2025
S M T W T F S Cost
   
1
2
3
4
5
$13,500.
6
7
8
9
10
11
12
$13,500.
13
14
15
16
17
18
19
$13,500.
20
21
22
23
24
25
26
$13,500.
27
28
29
30
31
    $13,500.
               
AUGUST 2025
S M T W T F S Cost
         
1
2
$13,500.
3
4
5
6
7
8
9
$15,000.
10
11
12
13
14
15
16
$15,000.
17
18
19
20
21
22
23
$14,500.
24
25
26
27
28
29
30
$13,500.
31
            $13,500.
SEPTEMBER 2025
S M T W T F S Cost
 
1
2
3
4
5
6
Call
7
8
9
10
11
12
13
Call
14
15
16
17
18
19
20
Call
21
22
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27
Call
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30
        Call