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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:
$2,000 - $3,800
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,000
6
7
8
9
10
11
12
$2,400
13
14
15
16
17
18
19
$2,400
20
21
22
23
24
25
26
$3,050
27
28
29
30
 $3,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$3,250
4
5
6
7
8
9
10
$3,250
11
12
13
14
15
16
17
$3,250
18
19
20
21
22
23
24
$3,500
25
26
27
28
29
30
31
$3,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$3,800
8
9
10
11
12
13
14
$3,800
15
16
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18
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20
21
$3,800
22
23
24
25
26
27
28
$3,500
29
30
31
 $2,100
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,100
5
6
7
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10
11
$2,100
12
13
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17
18
$2,100
19
20
21
22
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24
25
$2,100
26
27
28
29
30
 $2,100
Clean Fee: 
$400 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 - $6,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,000
6
7
8
9
10
11
12
$3,000
13
14
15
16
17
18
19
$3,600
20
21
22
23
24
25
26
$3,600
27
28
29
30
 $5,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,400
4
5
6
7
8
9
10
$5,700
11
12
13
14
15
16
17
$5,700
18
19
20
21
22
23
24
$5,700
25
26
27
28
29
30
31
$5,700
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,000
8
9
10
11
12
13
14
$6,000
15
16
17
18
19
20
21
$6,000
22
23
24
25
26
27
28
$6,000
29
30
31
 $5,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,400
5
6
7
8
9
10
11
$5,400
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $3,600
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
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Outstanding Waterfront Home & Guest House, Panoramic Views, Beach on the Lagoon, 5 Bedrooms, 4 Baths, AC

Gorgeous Expansive Waterfront Main & Guest Cottage, perfect for a multigenerational family vacation.  Spectacular views across and up the lagoon, this pristine home and guest cottage sits on just under two...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
5
Baths: 
4
Price Range:
$0 - $0
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSa
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September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

Two Week Minimum Stay Required per Owner

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Boutique Sweet with Designer Interior, Large Screened Porch, AC all Bedrooms, 15 Minute Walk to Oak Bluffs Center and Inkwell Beach

All newly remodeled and furnished and tucked away on a quiet Oak Bluffs lane for the perfect reprieve after a day at the beach and shopping in town, all just a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$4,000 - $7,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
6
7
8
9
10
11
12
$4,700
13
14
15
16
17
18
19
$4,700
20
21
22
23
24
25
26
$4,700
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
7
8
9
10
$5,500
11
12
13
14
15
16
17
$5,500
18
19
20
21
22
23
24
$5,990
25
26
27
28
29
30
31
$5,990
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,000
8
9
10
11
12
13
14
$10,000
15
16
17
18
19
20
21
$10,000
22
23
24
25
26
27
28
$7,000
29
30
31
 $5,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$4,700
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
 $4,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45
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Luxurious New Build 2024, 5 Bedroom, 5.5 Baths, 20 x 40 Heated Saltwater Pool with Spa, Expansive Deck wiith Outdoor Dining and Lounge Area, Association Tennis, Tucked in Sought After Deep Bottom Enclave of Homes

Welcome to this exquisite contemporary farmhouse nestled in the tranquil community of Deep Bottom in West Tisbury, just a short drive from the vibrant village centers of Edgartown and Oak...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$24,000 - $32,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$28,000
6
7
8
9
10
11
12
$28,000
13
14
15
16
17
18
19
$28,000
20
21
22
23
24
25
26
$28,000
27
28
29
30
 $30,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$30,000
4
5
6
7
8
9
10
$30,000
11
12
13
14
15
16
17
$28,000
18
19
20
21
22
23
24
$28,000
25
26
27
28
29
30
31
$28,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$32,000
8
9
10
11
12
13
14
$32,000
15
16
17
18
19
20
21
$32,000
22
23
24
25
26
27
28
$32,000
29
30
31
 $32,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$32,000
5
6
7
8
9
10
11
$32,000
12
13
14
15
16
17
18
$26,000
19
20
21
22
23
24
25
$28,000
26
27
28
29
30
 $28,000
Clean Fee: 
$900 per week
Tax: State & Local: 
11.7

Pool Heated to 82 in July & August included in rental rate. 

Pool Heated to 82 June & September additional propane surcharge, Please inquire with an agent! 

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Katama Luxury Home - Private Heated Pool with Pool Bar & Patio, Private Landscaped Yard, Screened Porch with Dining Area and Outdoor Living Room, Spacious Deck overlooks Yard & Pool, A/C

Outstanding Katama home set on two private acres and featuring summer living at its best.  Families will enjoy the beautifully furnished, large screened porch opening onto the deck overlooking the pool...Read more

Location: 
Katama
Sleeps: 
14
Bedrooms: 
6
Baths: 
4
Price Range:
$4,000 - $16,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$12,000
20
21
22
23
24
25
26
$13,500
27
28
29
30
 $14,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$14,000
4
5
6
7
8
9
10
$14,500
11
12
13
14
15
16
17
$14,500
18
19
20
21
22
23
24
$16,000
25
26
27
28
29
30
31
$16,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$16,000
8
9
10
11
12
13
14
$16,000
15
16
17
18
19
20
21
$16,000
22
23
24
25
26
27
28
$16,000
29
30
31
 $9,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $5,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7

Pool heated to 81 July & August included in the rental rate.

 

Pool heated to 81 degrees May, June, September & October an additional $300 propane surcharge.

 

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Lovely, bright summer get-away in ideal Edgartown setting

This attractive, open floor plan house has high ceilings with multiple skylights, creating the ideal bright, warm summer get-away. The house is perfectly located in the middle of it all,...Read more

Location: 
Edgartown
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$3,250 - $5,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,250
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
 $5,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,000
4
5
6
7
8
9
10
$5,000
11
12
13
14
15
16
17
$5,000
18
19
20
21
22
23
24
$5,000
25
26
27
28
29
30
31
$5,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,000
8
9
10
11
12
13
14
$5,000
15
16
17
18
19
20
21
$5,000
22
23
24
25
26
27
28
$5,000
29
30
31
 $3,250
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,250
5
6
7
8
9
10
11
$3,250
12
13
14
15
16
17
18
$3,250
19
20
21
22
23
24
25
$3,250
26
27
28
29
30
 $3,250
Clean Fee: 
$300 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 - $4,840
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,810
6
7
8
9
10
11
12
$3,810
13
14
15
16
17
18
19
$3,810
20
21
22
23
24
25
26
$3,810
27
28
29
30
 $4,840
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,840
4
5
6
7
8
9
10
$4,840
11
12
13
14
15
16
17
$4,840
18
19
20
21
22
23
24
$4,840
25
26
27
28
29
30
31
$4,840
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$4,840
8
9
10
11
12
13
14
$4,840
15
16
17
18
19
20
21
$4,840
22
23
24
25
26
27
28
$4,840
29
30
31
 $4,120
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,120
5
6
7
8
9
10
11
$4,120
12
13
14
15
16
17
18
$4,120
19
20
21
22
23
24
25
$4,120
26
27
28
29
30
 $4,120
Clean Fee: 
$310 per week, owner will provide sheets, towels, beach towels, additional $230 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $230 per rented period. 

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Menemsha Waterfront, Magnificent Views and Private Location, WiFi

This quintessential Chilmark cottage/home has been impeccably maintained,  The dining and living areas with spectacular views across Menemsha Channel to Aquinnah open to a wrap-around deck.  Enjoy spectacular water views...Read more

Location: 
Chilmark
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,640 - $8,240
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,640
6
7
8
9
10
11
12
$4,640
13
14
15
16
17
18
19
$6,180
20
21
22
23
24
25
26
$6,180
27
28
29
30
 $8,240
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,240
4
5
6
7
8
9
10
$8,240
11
12
13
14
15
16
17
$8,240
18
19
20
21
22
23
24
$8,240
25
26
27
28
29
30
31
$8,240
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$8,240
8
9
10
11
12
13
14
$8,240
15
16
17
18
19
20
21
$8,240
22
23
24
25
26
27
28
$8,240
29
30
31
 $8,240
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,240
5
6
7
8
9
10
11
$6,700
12
13
14
15
16
17
18
$6,700
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
 $6,700
Clean Fee: 
$385 per week, owner will provide sheets, towels, beach towels, additional $230 per rental period
Tax: State & Local: 
11.7

Owner will provide, sheets, towels & beach towels for an additional $230 per rented period. 

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Hidden Cove Summer Retreat, Newly Updated, Association Tennis Courts, Bike Paths at Entrance to Neighborhood, Multiple Beaches Near By

Summer Dream offers the opportunity for a relaxing vacation in a beautiful environment. This 4 bedroom, 2 ½ bath home has a beautiful new kitchen and new living room furnishings...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$0 - $0
June 2027
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
 $6,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$6,800
4
5
6
7
8
9
10
$7,200
11
12
13
14
15
16
17
$7,000
18
19
20
21
22
23
24
$7,000
25
26
27
28
29
30
31
$7,300
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$7,300
8
9
10
11
12
13
14
$7,800
15
16
17
18
19
20
21
$7,800
22
23
24
25
26
27
28
$7,300
29
30
31
 $6,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,800
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$420 per week
Tax: State & Local: 
14.45

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