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Adorable Updated 2 Bedroom 1.5 Bath Cottage, Walk to Town, Harbor and Beach

If you are looking for an adorable cottage-style home in the center of Oak Bluffs this newly updated, tastefully decorated 2 bedroom, with one full bath and a half bath, is sure to...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$2,500 - $3,000
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,500
8
9
10
11
12
13
14
$2,500
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,700
29
30
 $3,800
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,800
6
7
8
9
10
11
12
$3,800
13
14
15
16
17
18
19
$3,800
20
21
22
23
24
25
26
$3,800
27
28
29
30
31
 $3,800
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,800
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$3,500
31
 $3,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,000
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,500
28
29
30
 $2,500
Clean Fee: 
$275 per week
Tax: State & Local: 
11.7
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LODGJ

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Property Details
Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet
Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$2,900 - $2,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
$2,900
22
23
24
25
26
27
28
$2,900
29
30
 $3,000
July 2025
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
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$3,000
31
 $2,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,900
7
8
9
10
11
12
13
$2,900
14
15
16
17
18
19
20
$2,900
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$360 per week
Tax: State & Local: 
11.7
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PIKUT

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Property Details
Cozy Contemporary Home with Designer Interior Details , Centrally Located to Towns and Beaches

WELCOME TO SANDPIPER COTTAGE, YOUR STYLISH FAMILY RETREAT!

Four bedrooms include a primary bedroom with a queen bed on the 1st level with a television and a full bath across the...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$1,600 - $2,800
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,600
8
9
10
11
12
13
14
$2,600
15
16
17
18
19
20
21
$2,800
22
23
24
25
26
27
28
$3,200
29
30
 $3,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,500
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
$4,000
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$3,200
31
 $2,800
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,800
7
8
9
10
11
12
13
$2,600
14
15
16
17
18
19
20
$2,600
21
22
23
24
25
26
27
$1,600
28
29
30
 $1,600
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
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MELAF

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Property Details
Sparrow Lane House, Newly Furnished, Sleeps 7, Spacious Deck and Covered Porch both Overlook Lovely Landscaped Yard, AC in 3 Bedrooms

Lovely 4 bedroom (sleeps 7), 2 bath home,  set on large landscaped lot. The house has been tastefully and comfortably decorated with new furnishings

The first level hosts open concept Kitchen,...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,700 - $2,700
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,700
8
9
10
11
12
13
14
$2,700
15
16
17
18
19
20
21
$2,700
22
23
24
25
26
27
28
$2,700
29
30
 $3,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,900
6
7
8
9
10
11
12
$3,900
13
14
15
16
17
18
19
$3,900
20
21
22
23
24
25
26
$3,900
27
28
29
30
31
 $3,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,900
3
4
5
6
7
8
9
$3,900
10
11
12
13
14
15
16
$3,900
17
18
19
20
21
22
23
$3,900
24
25
26
27
28
29
30
$3,900
31
 $2,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,700
7
8
9
10
11
12
13
$2,700
14
15
16
17
18
19
20
$2,700
21
22
23
24
25
26
27
$2,700
28
29
30
 
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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MAYOJ

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Property Details
Central Location with Ease of Access to Village Centers and Multiple Beaches

Lovely vacation home budget-friendly in a quiet residential area and centrally located with a short drive to town centers of Oak Bluffs, Edgartown, and Vineyard Haven. Multiple Beaches 10 to 15-minute drive...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,200 - $2,700
June 2025
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
$2,700
29
30
 $2,900
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,900
6
7
8
9
10
11
12
$2,900
13
14
15
16
17
18
19
$2,900
20
21
22
23
24
25
26
$2,900
27
28
29
30
31
 $2,900
August 2025
SuMoTuWeThFrSaWeek
 1
2
$2,900
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$3,000
31
 $2,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,500
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,300
21
22
23
24
25
26
27
$2,300
28
29
30
 $2,300
Clean Fee: 
Included
Tax: State & Local: 
11.7
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FUSCM

(0)Inquire/Share
Property Details
Nicely Updated 4 bedroom Edgartown Home, Location 1.5 mi From Village Center, 10 minute Drive to Beaches. Miles of Bike Paths Nearby

Note: The kitchen is being remodeled for 2024 season!

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

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $2,550
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,550
8
9
10
11
12
13
14
$2,550
15
16
17
18
19
20
21
$2,550
22
23
24
25
26
27
28
$3,500
29
30
 $4,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,100
20
21
22
23
24
25
26
$4,500
27
28
29
30
31
 $4,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,500
3
4
5
6
7
8
9
$4,500
10
11
12
13
14
15
16
$4,500
17
18
19
20
21
22
23
$4,500
24
25
26
27
28
29
30
$3,700
31
 $2,500
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,500
7
8
9
10
11
12
13
$2,500
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,500
28
29
30
 
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7
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ADELC

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Property Details
Cozy Sunny 3 Bedroom Contemporary, Spacious Deck, Situated in a Quiet Neighborhood just on the outskirts of Vineyard Haven Village Center

Located on a quiet residential circle in Vineyard Haven, this pristine sweet home with oversized windows is contemporary, yet rustic with exposed wooden beams and a cathedral ceiling.  New natural travertine...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
3
Baths: 
2
Price Range:
$2,400 - $2,500
June 2025
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
$2,400
29
30
 $2,500
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$2,500
13
14
15
16
17
18
19
$2,500
20
21
22
23
24
25
26
$2,500
27
28
29
30
31
 $2,500
August 2025
SuMoTuWeThFrSaWeek
 1
2
$2,500
3
4
5
6
7
8
9
$2,770
10
11
12
13
14
15
16
$2,770
17
18
19
20
21
22
23
$2,770
24
25
26
27
28
29
30
$2,320
31
 
September 2025
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: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
gratd13-01-exterior.jpg
 
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GRATD

(0)Inquire/Share
Property Details
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 - $2,500
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,900
8
9
10
11
12
13
14
$3,900
15
16
17
18
19
20
21
$3,900
22
23
24
25
26
27
28
$4,200
29
30
 $4,600
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,600
6
7
8
9
10
11
12
$4,600
13
14
15
16
17
18
19
$4,600
20
21
22
23
24
25
26
$4,600
27
28
29
30
31
 $4,600
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,600
3
4
5
6
7
8
9
$4,600
10
11
12
13
14
15
16
$4,600
17
18
19
20
21
22
23
$4,600
24
25
26
27
28
29
30
$4,600
31
 $4,600
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,600
7
8
9
10
11
12
13
$4,000
14
15
16
17
18
19
20
$2,500
21
22
23
24
25
26
27
$2,000
28
29
30
 
Clean Fee: 
$260 per week
Tax: State & Local: 
11.7
Add Favorite
 
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STANJ

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Property Details
Sengekontacket - Waterfront Cottage, Panoramic Views and Amazing Sunrises

Charming Vintage Summer Cottage on Sengekontacket Pond

Experience the beauty of this vintage cottage perched on the shores of Sengekontacket Pond, offering stunning water views across the pond to North...Read more

Location: 
Edgartown
Sleeps: 
6
Bedrooms: 
4
Baths: 
2
Price Range:
$2,400 - $2,400
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,900
8
9
10
11
12
13
14
$1,900
15
16
17
18
19
20
21
$1,900
22
23
24
25
26
27
28
$1,900
29
30
 $3,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,700
6
7
8
9
10
11
12
$3,700
13
14
15
16
17
18
19
$3,700
20
21
22
23
24
25
26
$3,700
27
28
29
30
31
 $3,700
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,700
3
4
5
6
7
8
9
$3,700
10
11
12
13
14
15
16
$3,700
17
18
19
20
21
22
23
$3,700
24
25
26
27
28
29
30
$3,700
31
 $2,400
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,400
7
8
9
10
11
12
13
$2,400
14
15
16
17
18
19
20
$2,400
21
22
23
24
25
26
27
$2,400
28
29
30
 $2,400
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MCDOJ

(0)Inquire/Share
Property Details
Nestled on Quiet St 1 Mile from Village Center, Bike Paths to Town and Connecting Touring Trails at end of Street, Close to Edgartown Beaches.

Tucked away on a quiet lane just on the outskirts of Edgartown. This lovely 4 bedroom, 2 bath home is ideal for families up to 8 that want ease of ...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$2,350 - $2,350
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,300
8
9
10
11
12
13
14
$2,300
15
16
17
18
19
20
21
$2,300
22
23
24
25
26
27
28
$2,900
29
30
 $3,650
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,650
6
7
8
9
10
11
12
$3,650
13
14
15
16
17
18
19
$3,650
20
21
22
23
24
25
26
$3,650
27
28
29
30
31
 $4,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$4,000
3
4
5
6
7
8
9
$4,000
10
11
12
13
14
15
16
$4,000
17
18
19
20
21
22
23
$4,000
24
25
26
27
28
29
30
$3,200
31
 $2,350
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,350
7
8
9
10
11
12
13
$2,350
14
15
16
17
18
19
20
$2,350
21
22
23
24
25
26
27
$2,350
28
29
30
 $2,350
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
Add Favorite
 
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WATTL

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Property Details
Cottage with Screened Porch, Close to Menemsha Village Area and just a Short Drive to Lucy Vincent Beacn

Menemsha Crossroads sweet cottage in a private wooded area, perfect for a family of four. Features 2 bedrooms, a primary with bath, and the 2nd bedroom uses a hall bath. The...Read more

Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
2
Price Range:
$1,700 - $2,100
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$2,100
8
9
10
11
12
13
14
$2,100
15
16
17
18
19
20
21
22
23
24
25
26
27
28
$2,400
29
30
 $2,700
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,700
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
$2,800
27
28
29
30
31
 $3,000
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,000
3
4
5
6
7
8
9
$3,000
10
11
12
13
14
15
16
$3,000
17
18
19
20
21
22
23
$3,000
24
25
26
27
28
29
30
$2,600
31
 $1,700
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,700
7
8
9
10
11
12
13
$1,700
14
15
16
17
18
19
20
$1,700
21
22
23
24
25
26
27
$1,700
28
29
30
 
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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GOLLB

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Property Details
Waterfront, Private Beach, Gorgeous Water Views, Room AC, Wifi

MVVR EXCLUSIVE:  Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, and a great area for kayaking. The open kitchen, dining, and living areas are enhanced by...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
3
Baths: 
1
Price Range:
$1,850 - $1,950
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
8
9
10
11
12
13
14
$2,250
15
16
17
18
19
20
21
$2,650
22
23
24
25
26
27
28
$2,850
29
30
 $3,150
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,150
6
7
8
9
10
11
12
$3,150
13
14
15
16
17
18
19
$3,150
20
21
22
23
24
25
26
$3,150
27
28
29
30
31
 $3,250
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,250
3
4
5
6
7
8
9
$3,250
10
11
12
13
14
15
16
$3,250
17
18
19
20
21
22
23
$3,250
24
25
26
27
28
29
30
$2,850
31
 $1,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,950
7
8
9
10
11
12
13
$1,950
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $1,850
Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

Cottage books Tuesday to Tuesday July & August weeks

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DRAPG

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Property Details
Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $1,900
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,900
8
9
10
11
12
13
14
$1,900
15
16
17
18
19
20
21
$1,900
22
23
24
25
26
27
28
$1,900
29
30
 $2,100
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,100
6
7
8
9
10
11
12
$2,100
13
14
15
16
17
18
19
$2,100
20
21
22
23
24
25
26
$2,100
27
28
29
30
31
 $2,100
August 2025
SuMoTuWeThFrSaWeek
 1
2
$2,100
3
4
5
6
7
8
9
$2,100
10
11
12
13
14
15
16
$2,100
17
18
19
20
21
22
23
$2,100
24
25
26
27
28
29
30
$2,100
31
 $1,900
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,900
7
8
9
10
11
12
13
$1,900
14
15
16
17
18
19
20
$1,900
21
22
23
24
25
26
27
$1,900
28
29
30
 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
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DONVJ

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Property Details
Meadow House, 5 Minute Drive to Lambert's Cove Beach, Sleeps 6, AC, Private, Quiet Location yet close to Town and Beach, AC

Immaculately clean cabinesque home, privately located off of Lambert's Cove Rd, yet just a 5-minute drive to beautiful Lambert's Cove Beach and 10 minutes from Vineyard Haven town center. 

This three-bedroom home...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$1,750 - $1,750
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,700
8
9
10
11
12
13
14
$1,950
15
16
17
18
19
20
21
$1,950
22
23
24
25
26
27
28
$2,750
29
30
 $3,050
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,050
6
7
8
9
10
11
12
$3,050
13
14
15
16
17
18
19
$3,050
20
21
22
23
24
25
26
$3,350
27
28
29
30
31
 $3,350
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,350
3
4
5
6
7
8
9
$3,500
10
11
12
13
14
15
16
$3,500
17
18
19
20
21
22
23
$3,500
24
25
26
27
28
29
30
$3,200
31
 $1,950
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,950
7
8
9
10
11
12
13
$1,750
14
15
16
17
18
19
20
$1,750
21
22
23
24
25
26
27
$1,750
28
29
30
 $1,750
Clean Fee: 
$385 per week
Tax: State & Local: 
11.7
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KRAFM

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Property Details
Pristine Bungalow, Peekaboo Water View of Lagoon, Private Path to the Lagoon Waterfront from the Yard, 2 Kayaks Provided

THOREAU'S SPIRIT LIVES - An original 1920's summer bungalow lovingly restored to perfection. Two plus acres of quiet comfort, surrounded by farmland and woods. Walk down the long lawn past...Read more

Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2025
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$1,900
8
9
10
11
12
13
14
$2,300
15
16
17
18
19
20
21
$2,300
22
23
24
25
26
27
28
$2,950
29
30
 $2,950
July 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,950
6
7
8
9
10
11
12
$2,950
13
14
15
16
17
18
19
$2,950
20
21
22
23
24
25
26
$3,200
27
28
29
30
31
 $3,200
August 2025
SuMoTuWeThFrSaWeek
 1
2
$3,200
3
4
5
6
7
8
9
$3,200
10
11
12
13
14
15
16
$3,200
17
18
19
20
21
22
23
$3,700
24
25
26
27
28
29
30
$2,950
31
 $2,000
September 2025
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$2,000
7
8
9
10
11
12
13
$2,000
14
15
16
17
18
19
20
$2,000
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$375 per week
Tax: State & Local: 
11.7

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