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This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$70 - $5,000
June 2026
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
$4,000
28
29
30
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$6,000
16
17
18
19
20
21
22
$5,750
23
24
25
26
27
28
29
$5,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Note: Older style TVs seen in photos have been replaced. 

This bright and classic summer cottage is ideally located just one mile from Oak Bluffs town center and all the...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
1
Price Range:
$4,000 - $4,950
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 
July 2026
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
 $4,950
August 2026
SuMoTuWeThFrSaWeek
 1
$4,950
2
3
4
5
6
7
8
$4,950
9
10
11
12
13
14
15
$4,950
16
17
18
19
20
21
22
$4,950
23
24
25
26
27
28
29
$4,950
30
31
 $4,000
September 2026
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
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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1.5 Acres of Privacy, Bike Paths Adjacent to House, Association Pool, WiFi, Central A/C

West Tisbury - Newly updated and featuring 5 bedrooms and 4 baths.  Recently renovated including all new kitchen, updated baths, flooring, carpeting, walls painted, and lovely furnishings.  There is central AC on the 1st...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$3,500 - $4,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
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
 $5,900
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,900
5
6
7
8
9
10
11
$6,250
12
13
14
15
16
17
18
$6,250
19
20
21
22
23
24
25
$6,500
26
27
28
29
30
31
 $6,500
August 2026
SuMoTuWeThFrSaWeek
 1
$6,500
2
3
4
5
6
7
8
$6,500
9
10
11
12
13
14
15
$6,500
16
17
18
19
20
21
22
$6,500
23
24
25
26
27
28
29
$6,500
30
31
 $5,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,900
6
7
8
9
10
11
12
$4,900
13
14
15
16
17
18
19
$4,900
20
21
22
23
24
25
26
$4,900
27
28
29
30
 $3,900
Clean Fee: 
$450 per week, $600 per week with pet
Tax: State & Local: 
11.7
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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 2026
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
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,900
August 2026
SuMoTuWeThFrSaWeek
 1
$4,900
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
 
September 2026
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: 
$350 per week
Tax: State & Local: 
11.7
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Lovely Home in Island Grove Area of Edgartown Conveniently Located between South Beach and Edgartown Village. Association Tennis Courts and Pickleball Available to Renters

This recently updated home is tucked in the Island Grove area of Edgartown and is a perfect retreat for families & friends to gather. Located in a desirable neighborhood with access...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,800 - $4,800
June 2026
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
$4,800
28
29
30
 $5,280
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,280
5
6
7
8
9
10
11
$5,770
12
13
14
15
16
17
18
$5,770
19
20
21
22
23
24
25
$5,770
26
27
28
29
30
31
 $5,770
August 2026
SuMoTuWeThFrSaWeek
 1
$5,770
2
3
4
5
6
7
8
$6,470
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$4,800
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$525 per week
Tax: State & Local: 
11.7
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Edgartown Village, Walk to Town Center, Large Deck and Farmers Porch for Outdoor Enjoyment

Walk to Village Area from this sweet, cape-style home that features a farmer's porch across the front and a 12 x 20 mahogany deck across the back with an enclosed outside shower. 

The...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,800
June 2026
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
$4,200
21
22
23
24
25
26
27
$4,800
28
29
30
 $5,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
14
15
16
17
18
$5,400
19
20
21
22
23
24
25
$5,400
26
27
28
29
30
31
 $5,800
August 2026
SuMoTuWeThFrSaWeek
 1
$5,800
2
3
4
5
6
7
8
$5,800
9
10
11
12
13
14
15
$5,800
16
17
18
19
20
21
22
$5,800
23
24
25
26
27
28
29
$5,800
30
31
 $4,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,800
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
 $3,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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CENTRAL KATAMA LOCATION, BIKE TO BEACH OR TOWN, LARGE, PRIVATE BACKYARD, Central A/C

Note: Not seen in the photos displayed, the kitchen has new stone counters and a new stainless stove. 

Wonderful three-bedroom, two-bath home offering unique Vineyard character with raised, beamed ceilings and...Read more

Location: 
Katama
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,000 - $4,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,000
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$4,200
28
29
30
 $4,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,500
5
6
7
8
9
10
11
$4,500
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
 $4,800
August 2026
SuMoTuWeThFrSaWeek
 1
$4,800
2
3
4
5
6
7
8
$4,800
9
10
11
12
13
14
15
$4,800
16
17
18
19
20
21
22
$4,800
23
24
25
26
27
28
29
$4,800
30
31
 $3,000
September 2026
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
 $3,000
Clean Fee: 
$225 per week
Tax: State & Local: 
11.7

Ferry Tickets Available for purchase 6/28-7/5, 7/5-/12, 7/12-7/19, 7/19-7/26, & 7/26-8/2 - please inquire

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Ideally Located in Beautiful Major's Cove, Edgartown, Multiple Indoor & Outdoor Living Spaces, Perfect Family Vacation Home

Families and friends will feel right at home in this beautifully updated 4-bedroom, 2-bath contemporary retreat, comfortably accommodating up to 8 guests. Designed with both relaxation and gathering in mind,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,500 - $4,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,700
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
$3,900
28
29
30
 $4,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,800
5
6
7
8
9
10
11
$4,800
12
13
14
15
16
17
18
$4,800
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,200
August 2026
SuMoTuWeThFrSaWeek
 1
$5,200
2
3
4
5
6
7
8
$5,200
9
10
11
12
13
14
15
$5,700
16
17
18
19
20
21
22
$5,700
23
24
25
26
27
28
29
$5,200
30
31
 $3,750
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,750
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
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
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Cozy Cape, Newly Updated Summer 2023, Quiet Private Central Location, 4 Bedrooms, 3 Baths

Enjoy all the comforts of home in this tri-level updated Cape-style home set in a quiet cul de sac and bordered by lovely landscaping and mature oaks.   Multiple living spaces include the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,000 - $4,800
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,200
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$4,800
21
22
23
24
25
26
27
$5,600
28
29
30
 $5,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,700
5
6
7
8
9
10
11
$5,700
12
13
14
15
16
17
18
$5,700
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
31
 $6,000
August 2026
SuMoTuWeThFrSaWeek
 1
$6,000
2
3
4
5
6
7
8
$6,400
9
10
11
12
13
14
15
$6,900
16
17
18
19
20
21
22
$6,900
23
24
25
26
27
28
29
$6,300
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$3,200
13
14
15
16
17
18
19
$3,200
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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Waterfront, Water View, Walk to Beach

Casual immaculately clean in picturesque Menemsha, Chilmark waterfront. Beautiful views. A short stroll to the beach, fish market, boutiques, fishing, and shore dinners. Guest House - Main House on property...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$3,000 - $4,700
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,700
7
8
9
10
11
12
13
$3,700
14
15
16
17
18
19
20
$3,700
21
22
23
24
25
26
27
$3,700
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
$4,700
23
24
25
26
27
28
29
$4,700
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
27
28
29
30
 $4,000
Clean Fee: 
$300 per week, owner will provide sheets, towels, beach towels, additional $225 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $225 per rented period. 

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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:
$2,000 - $4,700
June 2026
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
$4,000
21
22
23
24
25
26
27
$4,300
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 $4,700
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,100
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,300
27
28
29
30
 $2,700
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
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Close to Edgartown Center and Beaches, Bike Paths 2/10 mile from house, Large and Private Deck, Central AC

This lovely 3 bedroom, 2.5 bath home features open concept living, dining, and kitchen areas. The spacious living and dining area opens via glass sliders to a large and private 20 x 40 ft...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $4,700
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,000
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $4,700
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,700
5
6
7
8
9
10
11
$4,700
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,700
26
27
28
29
30
31
 $4,700
August 2026
SuMoTuWeThFrSaWeek
 1
$4,700
2
3
4
5
6
7
8
$4,900
9
10
11
12
13
14
15
$4,900
16
17
18
19
20
21
22
$4,900
23
24
25
26
27
28
29
$4,700
30
31
 $4,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,200
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: 
$350 per week
Tax: State & Local: 
11.7

Ferry Tickets available 7/25-8/1 - please inquire

 

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Nicely Updated 4 bedroom Edgartown Home, Location 1.5 mi From Village Center, 10 minute Drive to Beaches. Miles of Bike Paths Nearby

Perfect family vacation home tucked on the outskirts of Edgartown just 1.5 miles to the village center and a 10-minute drive to South Beach and State Beach, and for those...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $4,650
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,750
7
8
9
10
11
12
13
$2,750
14
15
16
17
18
19
20
$2,750
21
22
23
24
25
26
27
$3,700
28
29
30
 $4,650
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,650
5
6
7
8
9
10
11
$4,650
12
13
14
15
16
17
18
$4,650
19
20
21
22
23
24
25
$4,650
26
27
28
29
30
31
 $4,650
August 2026
SuMoTuWeThFrSaWeek
 1
$4,650
2
3
4
5
6
7
8
$4,700
9
10
11
12
13
14
15
$4,700
16
17
18
19
20
21
22
$4,700
23
24
25
26
27
28
29
$3,900
30
31
 $2,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,900
6
7
8
9
10
11
12
$2,700
13
14
15
16
17
18
19
$2,700
20
21
22
23
24
25
26
$2,700
27
28
29
30
 $2,700
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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Makonikey, Water View, Walk to Private Association Beach, Large Yard Area.

Located in Makonikey,  a private enclave of homes on the North Shore.

Beautifully maintained four-bedroom vacation home with water views. Just a short walk or drive to private Makonikey association beach,  This...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$4,600 - $4,600
June 2026
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
 $4,600
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,600
5
6
7
8
9
10
11
$4,600
12
13
14
15
16
17
18
$4,600
19
20
21
22
23
24
25
$4,600
26
27
28
29
30
31
 
August 2026
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
31
 
September 2026
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: 
$270 per week
Tax: State & Local: 
11.7
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Waterfront, Water View, Lagoon Beach

This charming, recently renovated, waterfront home atop the lagoon bluffs, boasts spectacular sunsets and panoramic waterfront views of the Lagoon, outer Vineyard Haven Harbor, and Cape Cod from patios, living...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $4,600
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,300
7
8
9
10
11
12
13
$4,600
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
July 2026
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
31
 
August 2026
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
31
 
September 2026
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
$4,500
27
28
29
30
 $4,000
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7

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