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Gorgeous Waterfront Home on the Lagoon, Newly Renovated, 4 bedrooms, 3.5 Baths, Spectacular Waterviews, Upper & Lower Decks

Waterfront Retreat on the Lagoon – Oak Bluffs

This beautifully renovated waterfront home offers breathtaking views, a private sandy beach on the Lagoon, and a stylish, coastal-inspired interior. Nearly every room...Read more

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

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Property Details
Lovely Newly Renovated Waterfront Home on the Lagoon!

Tucked on Hines Point, a lovely neighborhood of lagoon front homes, this sweet 4 bedroom, 2 bath home has been completely updated and is only a 10-minute walk to Vineyard...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$3,800 - $7,550
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,100
7
8
9
10
11
12
13
$4,300
14
15
16
17
18
19
20
$4,600
21
22
23
24
25
26
27
$6,100
28
29
30
 $7,550
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,550
5
6
7
8
9
10
11
$7,550
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
 $8,950
August 2026
SuMoTuWeThFrSaWeek
 1
$8,950
2
3
4
5
6
7
8
$8,950
9
10
11
12
13
14
15
$8,950
16
17
18
19
20
21
22
$8,950
23
24
25
26
27
28
29
$7,200
30
31
 $5,200
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,200
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
 $4,500
Clean Fee: 
$385
Tax: State & Local: 
11.7

 

 

 

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NORTO

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Property Details
In-Town, Water View, Waterfront

Enjoy expansive harbor views and passing tall-masted schooners from the breezy wrap-around porch of this delightful five-bedroom classic Vineyard home over the harbor. Stroll to the village center, tennis, fine...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,500 - $5,500
June 2026
SuMoTuWeThFrSaWeek
 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
28
29
30
 $6,750
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,750
5
6
7
8
9
10
11
$6,750
12
13
14
15
16
17
18
$6,750
19
20
21
22
23
24
25
$6,750
26
27
28
29
30
31
 $6,750
August 2026
SuMoTuWeThFrSaWeek
 1
$6,750
2
3
4
5
6
7
8
$6,750
9
10
11
12
13
14
15
$6,750
16
17
18
19
20
21
22
$6,750
23
24
25
26
27
28
29
$6,750
30
31
 $5,500
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
 $5,500
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7
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NOTOA

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Property Details
Exclusive Makonikey Location, Custom Home with Designer Details, Private Association Beach

Hilltop Cottage, beautiful and custom-crafted with attention to details guests will appreciate. A completed gut renovation that includes AC throughout, two bedrooms and two baths, an open main living area with...Read more

Location: 
West Tisbury
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$2,750 - $4,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
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
$3,500
28
29
30
 $4,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
 $4,500
August 2026
SuMoTuWeThFrSaWeek
 1
$4,500
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$4,500
16
17
18
19
20
21
22
$4,500
23
24
25
26
27
28
29
$4,000
30
31
 $3,250
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,250
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
 $2,750
Clean Fee: 
$250 per week
Tax: State & Local: 
11.7
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OLIVK

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Property Details
Newly updated vacation retreat, 3 minute walk to association pool, 10 min drive to Lamberts Cove Beach or South Shore Beach

This lovely West Tisbury contemporary cape features multiple living spaces both indoors and out for your vacation enjoyment.  Just a 3-minute walk from the house to the association pool!  This home...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
3
Price Range:
$2,800 - $3,650
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,800
7
8
9
10
11
12
13
$2,800
14
15
16
17
18
19
20
$2,800
21
22
23
24
25
26
27
$3,400
28
29
30
 $3,450
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,450
5
6
7
8
9
10
11
$3,450
12
13
14
15
16
17
18
$3,550
19
20
21
22
23
24
25
$3,550
26
27
28
29
30
31
 $3,650
August 2026
SuMoTuWeThFrSaWeek
 1
$3,650
2
3
4
5
6
7
8
$3,650
9
10
11
12
13
14
15
$3,650
16
17
18
19
20
21
22
$3,650
23
24
25
26
27
28
29
$3,450
30
31
 $2,800
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,800
6
7
8
9
10
11
12
$2,800
13
14
15
16
17
18
19
$2,800
20
21
22
23
24
25
26
$2,800
27
28
29
30
 $2,800
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7
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PAILB

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Property Details
Exquisite all Newly Updated Contemporary Farm House Style Home! Heated Pool! Location!! 15 minute walk to Edgartown Village Center, 5 minute Drive to South Beach

Outstanding Edgartown Vacation Home!  Walk or bike to the center of Edgartown Village from this handsomely crafted, 5-bedroom, 3.5-bath vacation home. Multiple living spaces flow seamlessly from inside to the vaulted, 3-season screened...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,980 - $16,970
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$10,970
7
8
9
10
11
12
13
$10,970
14
15
16
17
18
19
20
$14,980
21
22
23
24
25
26
27
$14,980
28
29
30
 $16,970
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$16,970
5
6
7
8
9
10
11
$16,970
12
13
14
15
16
17
18
$16,970
19
20
21
22
23
24
25
$16,970
26
27
28
29
30
31
 $16,970
August 2026
SuMoTuWeThFrSaWeek
 1
$16,970
2
3
4
5
6
7
8
$16,970
9
10
11
12
13
14
15
$16,970
16
17
18
19
20
21
22
$17,970
23
24
25
26
27
28
29
$17,970
30
31
 $13,980
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,980
6
7
8
9
10
11
12
$10,970
13
14
15
16
17
18
19
$10,970
20
21
22
23
24
25
26
$10,970
27
28
29
30
 $8,980
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

Pool Heat to 82 degrees, included in rental rate July & August

Pool Heat to 82 degrees,  Shoulder season weeks additional $250 per week

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PAL77

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Property Details
Stunning Edgartown Village Center Retreat, Heated Pool & Spa, 26' x 11, 3 to 6 Feet Deep, Luxurious Amenities Throughout, 5 Bedrooms, 5 Baths , 2 Powder Rooms

Built in 1784 by Reverend Joseph “Parson” Thaxter, First Chaplain of the Revolutionary War and the town’s longtime minister, this storied residence has anchored the island’s history for more than...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$14,000 - $24,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$20,000
7
8
9
10
11
12
13
$20,000
14
15
16
17
18
19
20
$20,000
21
22
23
24
25
26
27
$20,000
28
29
30
 $24,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$24,000
5
6
7
8
9
10
11
$24,000
12
13
14
15
16
17
18
$24,000
19
20
21
22
23
24
25
$24,000
26
27
28
29
30
31
 $24,000
August 2026
SuMoTuWeThFrSaWeek
 1
$24,000
2
3
4
5
6
7
8
$24,000
9
10
11
12
13
14
15
$24,000
16
17
18
19
20
21
22
$24,000
23
24
25
26
27
28
29
$24,000
30
31
 $24,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$24,000
6
7
8
9
10
11
12
$24,000
13
14
15
16
17
18
19
$24,000
20
21
22
23
24
25
26
$24,000
27
28
29
30
 $18,000
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Pool heating fee: $300 per week (covers both pool and spa)

 

Pool is heated to 81 degrees during July & August,off season pool heat at additional cost please inquire.

 

Renters control the spa: Heats to 104°F in ~1 hour, auto shut-off after 3 hours

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PANDC

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Property Details
Coffin's Field, Main House, and Guest Apartment above Garage, Heated Pool - 16 x 32, Porch and Spacious Deck, 8 Minute Drive to Gorgeous Trustees / Long Point Beach

Lovely farmhouse-style 5-bedroom home with heated pool -16' x 32', 3 to 5 feet depth,  main house, and guest apartment over the garage centrally located and easily accessible to Long Point Beach and Edgartown...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $11,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$7,500
7
8
9
10
11
12
13
$8,950
14
15
16
17
18
19
20
$8,950
21
22
23
24
25
26
27
$8,950
28
29
30
 $10,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,800
5
6
7
8
9
10
11
$10,800
12
13
14
15
16
17
18
$10,800
19
20
21
22
23
24
25
$10,800
26
27
28
29
30
31
 $10,800
August 2026
SuMoTuWeThFrSaWeek
 1
$10,800
2
3
4
5
6
7
8
$12,900
9
10
11
12
13
14
15
$12,900
16
17
18
19
20
21
22
$12,900
23
24
25
26
27
28
29
$11,500
30
31
 $8,950
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,950
6
7
8
9
10
11
12
$8,950
13
14
15
16
17
18
19
$8,500
20
21
22
23
24
25
26
$8,500
27
28
29
30
 $6,000
Clean Fee: 
$675
Tax: State & Local: 
11.7

Pool & the Spa in the pool heated to 81 degrees, included in Rental Rate July & August Weeks. Spa not heated to higher temperatures and jets will be off. 

 

Pool & Spa  Heated to 81 degrees June & September weeks additional $300 propane surcharge per week. 

 

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PE585

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Property Details
Perfect Beach Front Cottage. Expansive Water Views, Gorgeous Sunsets, Pristine Modern Interior

Privately nestled atop a dune with breathtaking views and just steps from a private swimming beach. This immaculate 2 bedroom, 1 bath beachfront cottage offers a tastefully furnished interior with sun-filled rooms...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$4,040 - $7,090
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$5,530
7
8
9
10
11
12
13
$5,530
14
15
16
17
18
19
20
$5,530
21
22
23
24
25
26
27
$5,530
28
29
30
 $7,090
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,090
5
6
7
8
9
10
11
$7,090
12
13
14
15
16
17
18
$7,090
19
20
21
22
23
24
25
$7,090
26
27
28
29
30
31
 $7,090
August 2026
SuMoTuWeThFrSaWeek
 1
$7,090
2
3
4
5
6
7
8
$7,090
9
10
11
12
13
14
15
$7,090
16
17
18
19
20
21
22
$7,090
23
24
25
26
27
28
29
$6,560
30
31
 $6,040
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,040
6
7
8
9
10
11
12
$5,510
13
14
15
16
17
18
19
$4,990
20
21
22
23
24
25
26
$4,990
27
28
29
30
 $4,460
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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PEALY

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Property Details
Newly Updated Chilmark Cottage, Key to Private association Black Point Beach just 8/10ths mile from Cottage

For those who love Chilmark! Located in a very private setting off of Quenames Rd, this fresh and modern updated cottage comes with a key to private association Black Point...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$3,500 - $6,000
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
$4,000
21
22
23
24
25
26
27
$4,000
28
29
30
 $5,750
July 2026
SuMoTuWeThFrSaWeek
 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
SuMoTuWeThFrSaWeek
 1
$5,750
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
$6,000
23
24
25
26
27
28
29
$6,000
30
31
 $5,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,000
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
27
28
29
30
 $3,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

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