Karen M. Overtoom Logo
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 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$4,000.
7
8
9
10
11
12
13
$4,000.
14
15
16
17
18
19
20
$4,500.
21
22
23
24
25
26
27
$4,700.
28
29
30
        $4,700.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$4,700.
5
6
7
8
9
10
11
$5,600.
12
13
14
15
16
17
18
$5,600.
19
20
21
22
23
24
25
$5,600.
26
27
28
29
30
31
  $6,200.
               
AUGUST 2026
S M T W T F S Cost
           
1
$6,200.
2
3
4
5
6
7
8
$6,200.
9
10
11
12
13
14
15
$6,200.
16
17
18
19
20
21
22
$5,000.
23
24
25
26
27
28
29
$5,000.
30
31
          $5,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$5,000.
6
7
8
9
10
11
12
$5,000.
13
14
15
16
17
18
19
$5,000.
20
21
22
23
24
25
26
$5,000.
27
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 2026
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
23
24
25
26
27
Call
28
29
30
        $8,500.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$8,500.
5
6
7
8
9
10
11
$8,500.
12
13
14
15
16
17
18
$8,500.
19
20
21
22
23
24
25
$8,500.
26
27
28
29
30
31
  $15,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$15,000.
2
3
4
5
6
7
8
$15,000.
9
10
11
12
13
14
15
$15,000.
16
17
18
19
20
21
22
$15,000.
23
24
25
26
27
28
29
$15,000.
30
31
          $15,000.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$15,000.
6
7
8
9
10
11
12
Call
13
14
15
16
17
18
19
Call
20
21
22
23
24
25
26
Call
27
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 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$5,250.
7
8
9
10
11
12
13
$5,250.
14
15
16
17
18
19
20
$5,600.
21
22
23
24
25
26
27
$5,600.
28
29
30
        $6,800.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$6,800.
5
6
7
8
9
10
11
$6,800.
12
13
14
15
16
17
18
$6,800.
19
20
21
22
23
24
25
$6,800.
26
27
28
29
30
31
  $7,400.
               
AUGUST 2026
S M T W T F S Cost
           
1
$7,400.
2
3
4
5
6
7
8
$7,400.
9
10
11
12
13
14
15
$7,400.
16
17
18
19
20
21
22
$7,400.
23
24
25
26
27
28
29
$7,400.
30
31
          $7,400.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
$7,400.
6
7
8
9
10
11
12
$5,425.
13
14
15
16
17
18
19
$5,425.
20
21
22
23
24
25
26
$5,425.
27
28
29
30
      $5,425.
               

Gracious Oak Bluffs Home


"Elegant with Private Beach and Guest House"

Newly updated gracious house and guest house with a total of five bedrooms and a brand new screen porch. Private beach access and tennis / pickle ball courts. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a pee...Read the full description.

JUNE 2026
S M T W T F S Cost
 
1
2
3
4
5
6
$11,000.
7
8
9
10
11
12
13
$11,000.
14
15
16
17
18
19
20
$11,000.
21
22
23
24
25
26
27
$11,000.
28
29
30
        $14,000.
               
JULY 2026
S M T W T F S Cost
     
1
2
3
4
$14,000.
5
6
7
8
9
10
11
$14,000.
12
13
14
15
16
17
18
$14,000.
19
20
21
22
23
24
25
$14,000.
26
27
28
29
30
31
  $14,000.
               
AUGUST 2026
S M T W T F S Cost
           
1
$14,000.
2
3
4
5
6
7
8
$15,000.
9
10
11
12
13
14
15
$15,000.
16
17
18
19
20
21
22
$14,500.
23
24
25
26
27
28
29
$13,500.
30
31
          $13,500.
SEPTEMBER 2026
S M T W T F S Cost
   
1
2
3
4
5
Call
6
7
8
9
10
11
12
Call
13
14
15
16
17
18
19
Call
20
21
22
23
24
25
26
Call
27
28
29
30
      Call