Charming, 4-bedroom Oak Bluffs Home, pristinely maintained! The large wraparound porch and backyard patio areas provide the perfect venue for relaxing when not at the beach or out and about...Read more
Location:
Oak Bluffs
Sleeps:
7
Bedrooms:
4
Baths:
2
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$2,500
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,000
28
29
30
$5,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
$5,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,000
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$5,500
30
31
$5,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$5,000
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
$2,000
27
28
29
30
$2,000
Clean Fee:
$400 per week
Tax: State & Local:
11.7
Weekly rates reduced by $500 per week for available weeks in May, June & July
Captain Swain House, Elegant Main & Guest House, 4 Bedrooms, 4.5 Baths, Multiple Indoor/Outdoor Living Spaces, 5 Minute Walk to Town, Expansive Landscaped Yard
In-Town Vacation Retreat in the William Street Historic District Just a five-minute walk to the heart of town, this spacious and beautifully updated home blends modern comfort with timeless...Read more
Location:
Vineyard Haven
Sleeps:
10
Bedrooms:
4
Baths:
4
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$6,000
28
29
30
$5,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,500
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
$8,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,500
2
3
4
5
6
7
8
$10,000
9
10
11
12
13
14
15
$10,000
16
17
18
19
20
21
22
$10,000
23
24
25
26
27
28
29
$10,000
30
31
$7,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
$6,000
Clean Fee:
$875 per week
Tax: State & Local:
11.7
Rate reduced for week 6/27 - 7/4 - see calendar for adjusted rate
Cape Cod Village House, Upscale furnishings, Central A/C, WiFi, 20 Minute Walk Town, 1/2 Mile to Bike Path.
Three-plus bedroom cape is a short walk (20 minutes) into town, two and a half miles to beaches, and one-half mile to bike path. It is an ideal home for...Read more
Location:
Edgartown
Sleeps:
6
Bedrooms:
3
Baths:
2
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$5,420
7
8
9
10
11
12
13
$5,420
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
$5,750
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,750
5
6
7
8
9
10
11
$5,750
12
13
14
15
16
17
18
$5,750
19
20
21
22
23
24
25
$5,750
26
27
28
29
30
31
$5,750
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,750
2
3
4
5
6
7
8
$5,950
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$5,950
23
24
25
26
27
28
29
30
31
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
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 ($180 interim clean for rentals over 1 week)
Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Multiple Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road
Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$5,400
7
8
9
10
11
12
13
$5,400
14
15
16
17
18
19
20
$5,400
21
22
23
24
25
26
27
$5,400
28
29
30
$6,300
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$6,300
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
31
$6,900
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$6,900
2
3
4
5
6
7
8
$9,100
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$9,500
23
24
25
26
27
28
29
$6,900
30
31
$6,600
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,600
6
7
8
9
10
11
12
$5,900
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
$5,000
Clean Fee:
$500 per week ($375 for interim cleaning on multiple week rentals)
Pristine Water view Home, Located in the Community of Homes known as Water View Farms, Walk to Private Association Waterfront, Great Play Beach, Launch Kayaks
This charming updated home is set in idyllic Water View Farms overlooking Sengekontacket pond. This well-thought-out home offers a beautifully landscaped yard and cottage-style living with indoor spaces that transition...Read more
Classic Cape-style home privately situated on a quiet end of road location in the heart of the Katama area of Edgartown. Ideally located just 1.5 miles to Edgartown Village center...Read more
Charming & Cozy 2 Bedroom, 2 Bath Home, West Chop area of Vineyard Haven, Located on a Quiet Street, Close to Town & Beach
Note: Newly completed, not seen in photos, a 250 square foot deck has been added to the back of the house. The deck will have a patio dining table, and...Read more
Location:
Vineyard Haven
Sleeps:
4
Bedrooms:
2
Baths:
2
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$3,850
7
8
9
10
11
12
13
$3,850
14
15
16
17
18
19
20
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
$4,850
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,850
5
6
7
8
9
10
11
$4,850
12
13
14
15
16
17
18
$4,850
19
20
21
22
23
24
25
$4,850
26
27
28
29
30
31
$5,150
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,150
2
3
4
5
6
7
8
$5,150
9
10
11
12
13
14
15
$5,150
16
17
18
19
20
21
22
$5,150
23
24
25
26
27
28
29
$5,150
30
31
$5,150
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$5,150
6
7
8
9
10
11
12
$3,250
13
14
15
16
17
18
19
$3,250
20
21
22
23
24
25
26
$3,250
27
28
29
30
$3,250
Clean Fee:
$350 per week
Tax: State & Local:
11.7
Ferry Tickets Available 8/22-8/29 - please inquire
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
Classic Updated Gingerbread Cottage, 5 Minute Stroll Along Harbor to Beach and Town Center,
Classic Vineyard Oak Bluffs Cottage, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. The main living level features a lovely kitchen, very well stocked with...Read more
Location:
Oak Bluffs
Sleeps:
6
Bedrooms:
3
Baths:
2
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$3,000
14
15
16
17
18
19
20
$3,000
21
22
23
24
25
26
27
$3,500
28
29
30
$5,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,000
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
$5,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,000
2
3
4
5
6
7
8
$7,500
9
10
11
12
13
14
15
$7,500
16
17
18
19
20
21
22
$7,500
23
24
25
26
27
28
29
$5,000
30
31
$4,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
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:
$350 per week
Tax: State & Local:
11.7
Rates reduced for available weeks June - July - see calendar for adjusted rates
Hidden Cove Retreat, Walk to Association Tennis/Pickleball 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/pickleball courts. Its central location places it just a...Read more
Charming Katama Cape Style Home, Screened Porch with Dining, Deck and Farmers Porch, 3 minute drive to South Beach and 5 minute drive to Edgartown Village
A charming Katama home, set equidistance, 1.5 miles, between South Beach and Edgartown Village Center.
Multiple outdoor areas include a farmer's porch with rockers, a spacious screened porch with outdoor dining...Read more
Newly Updated Contemporary Home, I mile to Edgartown Village Center, Lovely Landscaped Yard Area!
Extended families will enjoy this modern, contemporary, open living style home set just on the outskirts of Edgartown center, just 1.8 miles into town and a short distance to State and South...Read more
