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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Show Rate Quote
Stunning, Luxury Harborfront Home with Pool, Descreetly Tucked in just off of Main St in Vineyard Haven, Expansive Waterviews across the Harbor!

Stunning Architect Designed Vineyard Waterfront Home with gorgeous water views overlooking the Vineyard Haven Harbor from the patio, private decks, screened porch, interior rooms, and the pool.  Walk to the...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
5
Bathrooms: 
4
Price Range:
$50,000 - $50,000
June 2023
SuMoTuWeThFrSaWeek
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 $50,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$50,000 /wk
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$50,000 /wk
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$50,000 /wk
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$50,000 /wk
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$50,000 /wk
30
31
 $50,000 /wk
August 2023
SuMoTuWeThFrSaWeek
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$50,000 /wk
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$50,000 /wk
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$50,000 /wk
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$50,000 /wk
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30
31
 $50,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$50,000 /wk
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Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7
Show Rate Quote
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. The owner provides 2 kayaks! Larger boats, skiffs, paddleboards,...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
6
Bathrooms: 
4
Price Range:
$12,502 - $35,000
June 2023
SuMoTuWeThFrSaWeek
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2
3
$13,006 /wk
4
5
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9
10
$13,006 /wk
11
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$17,500 /wk
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$17,500 /wk
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26
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29
30
 $17,500 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$17,500 /wk
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$30,002 /wk
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$30,002 /wk
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$30,002 /wk
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$30,002 /wk
30
31
 $35,000 /wk
August 2023
SuMoTuWeThFrSaWeek
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$35,000 /wk
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$35,000 /wk
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$35,000 /wk
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25
26
$25,000 /wk
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30
31
 $25,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$25,000 /wk
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$17,500 /wk
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$15,001 /wk
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$14,000 /wk
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$14,000 /wk
Clean Fee: 
$750 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!

Ferry Tickets available for 6/3-6/10, 9/2-9/9, 9/9-9/16. Please inquire!

Show Rate Quote
Quintessential West Chop Waterfront Home. Private Beach, Spectacular Views

Enjoy the essence of summer at this waterfront home with a private beach just 50 yards in front of the house. Evenings enjoy the magnificent sunsets while relaxing on the...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Bathrooms: 
5
Price Range:
$25,000 - $28,000
June 2023
SuMoTuWeThFrSaWeek
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25
26
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29
30
 $25,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$25,000 /wk
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$28,000 /wk
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$25,000 /wk
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$25,000 /wk
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$25,000 /wk
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 $28,000 /wk
August 2023
SuMoTuWeThFrSaWeek
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$28,000 /wk
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$28,000 /wk
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$28,000 /wk
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$25,000 /wk
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 $25,000 /wk
September 2023
SuMoTuWeThFrSaWeek
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$25,000 /wk
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Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
fielr12-01-view.jpg
Show Rate Quote
Exquisite West Chop Waterfront Home, Panoramic Ocean Views, Beach, Less than a Mile to Town Center

Grand West Chop Home, designed by a noted Vineyard Architect to highlight the magnificent water views. Surrounded by lush grounds and featuring an expansive bluestone patio, a place to gather, dine, relax and...Read more

Location: 
Vineyard Haven
Sleeps: 
10
Bedrooms: 
5
Bathrooms: 
4
Price Range:
$8,000 - $20,500
June 2023
SuMoTuWeThFrSaWeek
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2
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$10,500 /wk
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$11,500 /wk
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$12,500 /wk
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$13,500 /wk
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30
 $17,500 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$17,500 /wk
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$17,500 /wk
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$17,500 /wk
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$17,500 /wk
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$17,500 /wk
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 $20,500 /wk
August 2023
SuMoTuWeThFrSaWeek
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$20,500 /wk
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$20,500 /wk
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$20,500 /wk
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$20,500 /wk
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30
31
 $20,500 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$20,500 /wk
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$13,500 /wk
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$12,500 /wk
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$11,500 /wk
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$10,500 /wk
Clean Fee: 
$675 per week
Tax: State & Local: 
11.7
Show Rate Quote

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
Bathrooms: 
5
Price Range:
$7,000 - $20,500
June 2023
SuMoTuWeThFrSaWeek
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2
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$10,000 /wk
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$10,000 /wk
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$10,000 /wk
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$10,000 /wk
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 $16,500 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$16,500 /wk
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$16,750 /wk
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$16,750 /wk
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$16,750 /wk
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$18,500 /wk
30
31
 $20,500 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
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4
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$20,500 /wk
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$20,500 /wk
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$20,500 /wk
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25
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$18,500 /wk
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30
31
 $16,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$16,000 /wk
3
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$10,000 /wk
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$8,000 /wk
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$8,000 /wk
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$8,000 /wk
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.

Show Rate Quote
Located in the Heart of West Chop, Newly Updated. 12 min Walk to the Village Center, Spacious Patio, Modern Interior

Stately, classic home, located in the West Chop Area of Vineyard Haven.  Lovingly updated with state of the art kitchen and comfortable furnishings this vacation retreat is perfect for extended...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Bathrooms: 
3
Price Range:
$8,000 - $20,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$10,000 /wk
4
5
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$10,000 /wk
11
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$10,000 /wk
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$10,000 /wk
25
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29
30
 $12,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$12,000 /wk
2
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$12,000 /wk
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$12,000 /wk
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$12,000 /wk
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$12,000 /wk
30
31
 $15,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
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$15,000 /wk
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$15,000 /wk
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$20,000 /wk
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$20,000 /wk
27
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30
31
 $15,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$15,000 /wk
3
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$10,000 /wk
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$10,000 /wk
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$10,000 /wk
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$10,000 /wk
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Show Rate Quote
Waterfront & Beachfront

The Beach House  There are few homes anywhere on the island directly on a sandy swimming beach like Beach House. If you love a sunset, and water views that seemingly never...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
5
Bathrooms: 
3
Price Range:
$8,500 - $16,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$9,500 /wk
4
5
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$9,500 /wk
11
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$14,500 /wk
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$14,500 /wk
25
26
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29
30
 $16,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$16,000 /wk
2
3
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$16,000 /wk
9
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$16,000 /wk
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$16,000 /wk
23
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$16,000 /wk
30
31
 $16,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$16,000 /wk
6
7
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$16,000 /wk
13
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$16,000 /wk
20
21
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24
25
26
$16,000 /wk
27
28
29
30
31
 $10,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$10,000 /wk
3
4
5
6
7
8
9
$15,000 /wk
10
11
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$15,000 /wk
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$15,000 /wk
24
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$13,500 /wk
Clean Fee: 
$600
Tax: State & Local: 
11.7
Show Rate Quote
Architect Designed, All Newly Renovated, West Chop Area, Water views, Walk to Town, Swim Just a Half Block From the House, Quiet Exclusive Area!

All-New, Light & Airy Luxury Home in West Chop Area, designed by renowned architect Patrick Ahearn. A thoughtful blend of coastal and designer touches throughout makes this upscale vacation home perfect for...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
6
Bathrooms: 
6
Price Range:
$11,000 - $15,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$11,000 /wk
4
5
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10
$11,000 /wk
11
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$11,000 /wk
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24
$11,000 /wk
25
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29
30
 $12,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$12,000 /wk
2
3
4
5
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$13,500 /wk
9
10
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15
$13,500 /wk
16
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$13,500 /wk
23
24
25
26
27
28
29
$13,500 /wk
30
31
 $15,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$15,000 /wk
6
7
8
9
10
11
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$15,000 /wk
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$15,000 /wk
20
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25
26
$15,000 /wk
27
28
29
30
31
 
September 2023
SuMoTuWeThFrSa
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Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
urmst-01-exterior.jpg
Show Rate Quote
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
Bathrooms: 
2
Price Range:
$11,500 - $13,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$11,500 /wk
4
5
6
7
8
9
10
$11,500 /wk
11
12
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14
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$11,500 /wk
18
19
20
21
22
23
24
$11,500 /wk
25
26
27
28
29
30
 $13,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$13,000 /wk
2
3
4
5
6
7
8
$13,000 /wk
9
10
11
12
13
14
15
$13,000 /wk
16
17
18
19
20
21
22
$13,000 /wk
23
24
25
26
27
28
29
$13,000 /wk
30
31
 $13,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$13,000 /wk
6
7
8
9
10
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12
$13,000 /wk
13
14
15
16
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18
19
$13,000 /wk
20
21
22
23
24
25
26
$13,000 /wk
27
28
29
30
31
 $11,500 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$11,500 /wk
3
4
5
6
7
8
9
$11,500 /wk
10
11
12
13
14
15
16
$11,500 /wk
17
18
19
20
21
22
23
$11,500 /wk
24
25
26
27
28
29
30
$11,500 /wk
Clean Fee: 
$750 per rental period
Tax: State & Local: 
11.7
Show Rate Quote
Waterfront on the Lagoon, Spectacular Views, Tri-Level Home, Multiple Living Spaces

MVVR EXCLUSIVE:  Wonderful family-friendly waterfront on the lagoon home! This home is tucked on quiet Hines Point, a finger peninsula that stretches into the lagoon.  Impeccably maintained, this 4 bedroom, 4 bath home...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Bathrooms: 
4
Price Range:
$5,500 - $12,000
June 2023
SuMoTuWeThFrSa
 1
2
3
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25
26
27
28
29
30
 
July 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
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7
8
$9,300 /wk
9
10
11
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13
14
15
$9,300 /wk
16
17
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19
20
21
22
$12,000 /wk
23
24
25
26
27
28
29
$12,000 /wk
30
31
 $12,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000 /wk
6
7
8
9
10
11
12
$12,000 /wk
13
14
15
16
17
18
19
$12,000 /wk
20
21
22
23
24
25
26
$12,000 /wk
27
28
29
30
31
 $10,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$10,000 /wk
3
4
5
6
7
8
9
$8,000 /wk
10
11
12
13
14
15
16
$7,000 /wk
17
18
19
20
21
22
23
$7,000 /wk
24
25
26
27
28
29
30
$7,000 /wk
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Show Rate Quote
Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Families and friends are sure to enjoy this pristinely maintained and spacious home situated in a private and quiet location. Beautiful yard and deck area with outdoor seating and a patio dining area that...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Bathrooms: 
4
Price Range:
$5,500 - $12,000
June 2023
SuMoTuWeThFrSa
 1
2
3
4
5
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July 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$7,500 /wk
23
24
25
26
27
28
29
$7,500 /wk
30
31
 $8,500 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,500 /wk
6
7
8
9
10
11
12
$12,000 /wk
13
14
15
16
17
18
19
$12,000 /wk
20
21
22
23
24
25
26
$9,000 /wk
27
28
29
30
31
 $7,500 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$7,500 /wk
3
4
5
6
7
8
9
$6,000 /wk
10
11
12
13
14
15
16
$5,500 /wk
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Clean Fee: 
$550 weekly, Sheets & Towels $175
Tax: State & Local: 
11.7

Ferry Tickets available, 7/16 to 23, 7/23 to 7/30.,  7/30 to 8/6, 8/13 to 8/20

 

Sheets and towels provided at additional cost of $175 per week. Beach towels not provided. 

 

 

 

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

NOTE:  Owners adding new in-ground salt water heated pool 13 x 30 and 4.3 feet deep to 6 feet deep end to end. 

Set in a lovely enclave of homes...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Bathrooms: 
3
Price Range:
$8,500 - $12,000
June 2023
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
 
July 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
$12,000 /wk
9
10
11
12
13
14
15
$12,000 /wk
16
17
18
19
20
21
22
$12,000 /wk
23
24
25
26
27
28
29
$12,000 /wk
30
31
 $12,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000 /wk
6
7
8
9
10
11
12
$12,000 /wk
13
14
15
16
17
18
19
$12,000 /wk
20
21
22
23
24
25
26
$12,000 /wk
27
28
29
30
31
 $12,000 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$12,000 /wk
3
4
5
6
7
8
9
$8,500 /wk
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
Clean Fee: 
$850 per week
Tax: State & Local: 
11.7

Ferry Tickets available, 7/9 to 7/16 & 7/16 to 7/23

 

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

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

Show Rate Quote
Gorgeous Waterfront home and Separate Guest House, Spectacular Water views and Sunsets

Gorgeous waterfront home featuring 6 bedrooms and 3.5 baths; Four bedrooms and 2.5 baths in the main house and 2 bedrooms, separate kitchen, living area and 1 bath in the guest house,...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Bathrooms: 
3
Price Range:
$11,775 - $11,775
June 2023
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
 
July 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$11,775 /wk
23
24
25
26
27
28
29
$11,775 /wk
30
31
 $11,775 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,775 /wk
6
7
8
9
10
11
12
$11,775 /wk
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
September 2023
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: 
$375 per week
Tax: State & Local: 
11.7
Show Rate Quote
Newly refurbished Tri Level, Gorgeous Water Views of North Shore in Exclusive Makonikey Area

Spacious Post & Beam Vacation Home with Beachy vibe rooms filled with light through oversize windows. All newly updated with substantial water views of the North Shore and private association...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
4
Bathrooms: 
3
Price Range:
$4,800 - $11,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$5,500 /wk
4
5
6
7
8
9
10
$5,500 /wk
11
12
13
14
15
16
17
$5,500 /wk
18
19
20
21
22
23
24
$6,500 /wk
25
26
27
28
29
30
 $8,500 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$8,500 /wk
2
3
4
5
6
7
8
$10,000 /wk
9
10
11
12
13
14
15
$10,000 /wk
16
17
18
19
20
21
22
$10,000 /wk
23
24
25
26
27
28
29
$11,000 /wk
30
31
 $11,000 /wk
August 2023
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$11,000 /wk
6
7
8
9
10
11
12
$11,000 /wk
13
14
15
16
17
18
19
$11,000 /wk
20
21
22
23
24
25
26
$11,000 /wk
27
28
29
30
31
 $9,500 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$9,500 /wk
3
4
5
6
7
8
9
$6,500 /wk
10
11
12
13
14
15
16
$5,500 /wk
17
18
19
20
21
22
23
$5,500 /wk
24
25
26
27
28
29
30
$5,500 /wk
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

Show Rate Quote
Beautiful 3 Bedroom, 3.5 bath Home, Blustone Patio with Outdoor Dining & Grill , Landscaped. Situated on Quiet Street, Walk to Town
Location: 
Vineyard Haven
Sleeps: 
6
Bedrooms: 
3
Bathrooms: 
3
Price Range:
$6,000 - $10,000
June 2023
SuMoTuWeThFrSaWeek
 1
2
3
$6,000 /wk
4
5
6
7
8
9
10
$6,000 /wk
11
12
13
14
15
16
17
$6,000 /wk
18
19
20
21
22
23
24
$6,500 /wk
25
26
27
28
29
30
 $7,000 /wk
July 2023
SuMoTuWeThFrSaWeek
 1
$7,000 /wk
2
3
4
5
6
7
8
$8,600 /wk
9
10
11
12
13
14
15
$8,600 /wk
16
17
18
19
20
21
22
$8,600 /wk
23
24
25
26
27
28
29
$8,800 /wk
30
31
 
August 2023
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
$10,000 /wk
27
28
29
30
31
 $8,500 /wk
September 2023
SuMoTuWeThFrSaWeek
 1
2
$8,500 /wk
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: 
$500 per week
Tax: State & Local: 
11.7

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