Vineyard Haven Vacation Rentals

Vineyard Haven, Martha’s Vineyard’s primary port town, is the perfect place for vacation rental guests who want to be close the action. While staying in a Vineyard Haven vacation rental, you have direct access to the waterfront and Vineyard Haven’s many fun events, world-famous restaurants, and classic bars. Vacations in Vineyard Haven are full of excitement and fun on the water, and going out in Vineyard Haven after a day at the beach gives you the classic Martha’s Vineyard experience.

 

 

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Luxurious Home, Privately Situated in the West Chop Area of Vineyard Haven, Heated Pool, Spa, North Shore Waterviews, Multiple Indoor/Outdoor LIving Spaces. 6 Bedrooms, 5.5 Baths Sleeps 13.

Exceptional Luxury Rental: Elegant 6-Bedroom Estate in West Chop, Vineyard Haven

Experience refined summer living in this stunning six-bedroom, five-and-a-half-bath coastal retreat, ideally located in the prestigious West Chop area...Read more

Location: 
Vineyard Haven
Sleeps: 
13
Bedrooms: 
6
Baths: 
5
Price Range:
$14,000 - $35,000
June 2027
SuMoTuWeThFrSaWeek
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 $25,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$25,000
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$25,000
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$30,000
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$30,000
25
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30
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$35,000
August 2027
SuMoTuWeThFrSaWeek
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$35,000
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$35,000
15
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$35,000
22
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27
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$35,000
29
30
31
 $25,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$25,000
5
6
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$18,000
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$18,000
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24
25
26
27
28
29
30
 
Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

 

 

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GREJN

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Property Details
Stunning New Custom Home, Heated Pool, 20' x 36', 5 Bedrooms, 5 Bath, West Chop Area of Vineyard Haven

Welcome to this exceptional contemporary executive retreat, nestled within a newly developed enclave in the highly sought-after West Chop area of Vineyard Haven. Thoughtfully custom-built and offering nearly 4,200 square...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$18,000 - $30,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$18,000
6
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$18,000
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$18,000
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$20,000
27
28
29
30
 $20,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$20,000
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$20,000
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$25,000
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$25,000
25
26
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30
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$25,000
August 2027
SuMoTuWeThFrSaWeek
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$30,000
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$30,000
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$30,000
22
23
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$25,000
29
30
31
 $25,000
September 2027
SuMoTuWeThFrSaWeek
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$25,000
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$20,000
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$20,000
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$20,000
26
27
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29
30
 $18,000
Clean Fee: 
$900 per week
Tax: State & Local: 
11.7

Pool Heated to 82 Degrees, included in Rental Rate July & August.

Pool Heated to 82. Degrees, June, September,  Additional Charge $250 per week.  May & October weeks additional cost, please inquire! 

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HODGE

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Property Details
Stunning Waterfront Home on the Lagoon, Complete Renovation and Professionally Decorated. Private Beach Area and Dock, Perfect Retreat for Extended Families, Walk to Town. Swim, Sun, Kayak or Bring your own boat.

Exquisite waterfront family compound sleeps 12, with 270-degree water view of the Lagoon,  85' of sandy beach on the lagoon, and a private dock for boaters. Private dock (12' draft) with mooring and private sandy...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$8,500 - $25,000
June 2027
SuMoTuWeThFrSaWeek
 1
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3
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5
$14,250
6
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$14,250
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$14,250
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$14,250
27
28
29
30
 $20,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$20,250
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10
$20,250
11
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$20,250
18
19
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$22,500
25
26
27
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30
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$25,000
August 2027
SuMoTuWeThFrSaWeek
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$25,000
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$25,000
15
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$25,000
22
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$22,000
29
30
31
 $14,000
September 2027
SuMoTuWeThFrSaWeek
 1
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$14,000
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$12,000
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$11,000
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$11,000
26
27
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29
30
 $11,000
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Private Dock plus Mooring that draws 12 feet. If you plan to bring a boat please speak with the agent for details as must be approved by owner!

 

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COS67

Inquire
Property Details
Beautiful 3 Bedroom, 3.5 bath Home, Bluestone Patio with Outdoor Dining & Grill , Lovely Landscaped Yard. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
3
Baths: 
3
Price Range:
$6,000 - $24,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
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5
$6,000
6
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$6,000
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$6,000
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$6,000
27
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29
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 $7,500
July 2027
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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$7,500
25
26
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$7,500
August 2027
SuMoTuWeThFrSaWeek
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$10,000
8
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$24,500
15
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$24,500
22
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$8,500
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$7,000
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$6,500
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$6,500
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$6,500
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29
30
 $6,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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MONLC

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Property Details

Gorgeous estate home on large acreage, gorgeous water views with the ferry passing to and from the Vineyard, heated pool with patio surround, and an outdoor kitchen and patio dining...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Baths: 
5
Price Range:
$7,000 - $20,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
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5
$10,000
6
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$10,000
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$10,000
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$16,500
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30
 $16,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
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$16,750
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5
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$16,750
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$16,750
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$18,500
25
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30
31
$20,500
August 2027
SuMoTuWeThFrSaWeek
1
2
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$20,500
8
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$20,500
15
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$18,500
22
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25
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27
28
$16,000
29
30
31
 $10,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$10,000
5
6
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$8,000
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$8,000
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$8,000
26
27
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29
30
 $7,000
Clean Fee: 
$900 per week
Tax: State & Local: 
11.7

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

 

June & September weeks heated to 81 degrees additional $300 propane surcharge per week.

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ARONA

Inquire
Property Details
Superior New Luxury Build, Waterfront on the Lagoon, Multiple Indoor/Outdoor living Spaces. Private Association Beach Key, Deep Water Mooring

Nestled on Hines Point in Vineyard Haven, The Epitome of Summer Living offers sweeping vistas of the water from every room. With a sprawling screened porch, an upper-level deck, and...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$11,000 - $20,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
August 2027
SuMoTuWeThFrSaWeek
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$20,000
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner provides a key to a beautiful private association Beach in Chilmark, Quansoo Beach, approximately a 25 minute drive from the house. Worth the drive!

 

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TAVAM

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Property Details
Outstanding, Newly Updated Vacation Retreat, Heated Saltwater Pool. Multiple Living Spaces, All New Kitchen, Gorgeous Yard, Set in Quiet, Lovely Commmunity of Homes, Stonegate

Impeccable Vacation Getaway with Updated Amenities and a Heated Saltwater Pool

Nestled within the serene community of Stonegate, this exceptional retreat offers a rejuvenating escape. Conveniently located just a brief...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $16,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000
6
7
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10
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12
$11,000
13
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$11,000
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$11,000
27
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29
30
 $13,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,000
4
5
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10
$13,000
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$13,000
18
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$13,000
25
26
27
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29
30
31
$16,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$16,000
8
9
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$16,000
15
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20
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$16,000
22
23
24
25
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27
28
$14,000
29
30
31
 $11,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,000
5
6
7
8
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10
11
$8,000
12
13
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15
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$8,000
19
20
21
22
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24
25
$8,000
26
27
28
29
30
 $8,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Rate reduced for the last week in August - see calendar for rate

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

Spa area in the pool is heated to the same temperature as the pool and is not available Spa jets are also not available for renter use. 

 

Pool heated to 82 June & September when weeks are available additional $300 per week propane surcharge.

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THOHP

Inquire
Property Details
Exquisite New Contemporary Waterfront Home, Multiple Indoor& Outdoor Living Spaces with Waterviews.

This stunning luxury waterfront home, nestled on the Lagoon, offers breathtaking water views from every corner of the newly built residence. Enjoy the seamless transition between indoor and outdoor living...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
3
Baths: 
4
Price Range:
$12,500 - $16,000
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
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September 2027
SuMoTuWeThFrSa
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29
30
 
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7

Owner requires two week minimum booking during months July & August

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URMST

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Property Details
West Chop, Waterfront, Private Beach

Summer Compound in a majestic location.  Vintage vacation home perfect for large family gatherings.  Enjoy sweeping ocean views from the large comfortably furnished veranda.  A large screened porch offers seating...Read more

Location: 
Vineyard Haven
Sleeps: 
14
Bedrooms: 
6
Baths: 
2
Price Range:
$15,600 - $15,600
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
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11
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29
30
 $15,600
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$15,600
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5
6
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10
$15,600
11
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$15,600
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19
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21
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23
24
$15,600
25
26
27
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29
30
31
$15,600
August 2027
SuMoTuWeThFrSaWeek
1
2
3
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5
6
7
$15,600
8
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$15,600
15
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$15,600
22
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$15,600
29
30
31
 
September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$875 per rental period
Tax: State & Local: 
11.7
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BAYLM

Inquire
Property Details
Spectacular Waterfront Views in exclusive Makonikey area, Ocean Views and Breathtaking Sunsets, Private Beach, Private Location

This serene waterfront retreat offers sweeping water views in an exceptionally private setting, yet is just a 10-minute drive from town, with access to fine dining, shopping, galleries, and entertainment....Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$12,000 - $12,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$12,000
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September 2027
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Owner reduced rate for week 8/1 - see calendar for adjusted rate

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SAGID

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Property Details
Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Stunning Hilltop Post & Beam Vacation Home with a relaxed coastal ambiance and picturesque distant water vistas! Nestled off Lambert’s Cove Rd in Vineyard Haven, this exquisite property resides within...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $12,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,800
6
7
8
9
10
11
12
$5,800
13
14
15
16
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21
22
23
24
25
26
$6,800
27
28
29
30
 $11,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$11,000
4
5
6
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9
10
$11,000
11
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$11,000
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$12,000
25
26
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$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
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6
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$12,000
8
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$12,000
15
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$12,000
22
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25
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$10,000
29
30
31
 $7,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,000
5
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$6,500
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$6,500
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$6,500
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 $5,000
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

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WIL14

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Property Details

Classic updated 7 bedrooms, 5 bath West Chop Home. Nestled on a large landscaped lot on Hatch Rd in Vineyard Haven this spacious home offers the best in vacation home...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
7
Baths: 
5
Price Range:
$10,000 - $11,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7
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CLE20

Inquire
Property Details
Outer Harbor Waterfront, West Chop Area, Private Sandy Beach, Lush Gardens and Large Yard, Magnificent Water Views

NOTE: New upgrades for 2026 Rental Season: Mini Split AC units in the Living Area, Kitchen, and Bedrooms,  New Sofa in the Living Area, Newly Painted,  All new Windows throughout the House....Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$4,500 - $10,500
June 2027
SuMoTuWeThFrSaWeek
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$4,700
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$5,500
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$5,500
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$8,100
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 $8,500
July 2027
SuMoTuWeThFrSaWeek
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$8,500
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$9,000
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$9,000
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$9,500
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$10,000
August 2027
SuMoTuWeThFrSaWeek
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$10,500
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$10,500
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$10,500
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$10,000
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 $6,000
September 2027
SuMoTuWeThFrSaWeek
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$6,000
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$5,500
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$5,500
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$5,500
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30
 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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SHAJO

Inquire
Property Details

Step into this exquisite Victorian-style residence, meticulously renovated to preserve its original allure while offering a sanctuary away from the bustle of everyday life. Nestled in the picturesque town of...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $10,000
June 2027
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July 2027
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August 2027
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September 2027
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
kerr413-01-exterior.jpg
 
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KERR4

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Property Details
Sophisticated & Charming Waterfront Cottage, Large Waterfront Deck, Dock, Tennis Court, Spectacular Views

Stunning cottage style home where the wate front is literally at your doorstep. Lake Tashmoo is a large saltwater inlet great for swimming, sailing, and boating with access to the ocean.  Relax on the...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$9,500 - $9,500
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
August 2027
SuMoTuWeThFrSaWeek
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$9,500
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$9,500
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$9,500
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$9,500
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 $9,500
September 2027
SuMoTuWeThFrSaWeek
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$9,500
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Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

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