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East Chop Waterfront, Extraordinary Sunsets &Views Across the Sound , Deck directly on the Beach, Casual Interior

Classic, casual beachfront home combines cottage styling with modern amenities. spectacular views, quietly lapping waves right outside your windows, and breathtaking sunsets. Ideally located in the East Chop Area of Oak Bluffs just a short distance...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$6,000 - $6,000
June 2027
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July 2027
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September 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7

 

 

 

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CENCR

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Property Details
Oak Bluffs Summer Retreat, Large Private Deck, Lagoon Beach Rights -Great Area for Kayaking.

Spacious sun-filled home features open living spaces, hardwood floors throughout, 4 bedrooms and sleeps 8.

Exterior features include two decks, one sunny deck at the front of the house, and a large private...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $4,000
June 2027
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July 2027
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September 2027
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Clean Fee: 
$480 per week
Tax: State & Local: 
11.7
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CHA22

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Property Details
Gorgeous New Build, Contemporary Farmhouse Design, Heated Pool, Large Yard & Lawn Area, Sleeps 9, 3 bedrooms + Bonus Sleep Space on Lower Level, 3 Baths, 2 Half Baths

Luxurious new custom-built Katama area home with heated 14’ x 30’ pool. Ideally located just one mile to the village center and 1.5 miles to South Beach! Bike paths in...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
4
Baths: 
3
Price Range:
$6,000 - $17,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$8,500
6
7
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$17,000
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$10,500
20
21
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$11,500
27
28
29
30
 $15,000
July 2027
SuMoTuWeThFrSaWeek
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$15,000
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$17,000
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$17,000
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$17,000
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$18,500
August 2027
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$20,000
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$17,000
29
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 $9,000
September 2027
SuMoTuWeThFrSaWeek
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$9,000
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$7,500
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$7,000
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 $6,000
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Three-night minimum first two weeks of June 2025 and after September 6th

Pool Heated to 81 degrees, included in rental rate, July & August weeks. 

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

 

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CHAMV

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Property Details
WATER VIEW, IN TOWN - 2 MINUTE WALK TO MAIN ST, WIFI, A/C

In-Town Luxury Home. This state-of-the-art home features a large living room with a dining area and a gourmet kitchen with Viking and Sub Zero appliances. Each of the 4 bedrooms...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,250 - $7,990
June 2027
SuMoTuWeThFrSaWeek
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$7,990
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$7,990
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$7,990
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$7,990
27
28
29
30
 $10,500
July 2027
SuMoTuWeThFrSaWeek
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2
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$10,500
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$10,500
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$10,500
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$10,500
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31
$10,500
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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$10,500
29
30
31
 $7,990
September 2027
SuMoTuWeThFrSaWeek
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$7,990
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$7,990
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$7,990
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$7,990
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29
30
 $6,990
Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
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CHAVG

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Property Details
Deep Bottom, Oustanding New Contemporary Designer Home, 10 x 52" Heated Pool, Walk to Association Tennis Courts

Deep Bottom | Exceptional New Contemporary Designer Home with Heated 10' x 52' Pool | Walk to Association Tennis

Discover refined Vineyard living at this striking new contemporary retreat set...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$10,000 - $18,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$10,000
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7
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$10,000
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$10,000
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21
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$13,000
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28
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30
 $16,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$16,000
4
5
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10
$15,500
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$15,000
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$15,000
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$17,500
August 2027
SuMoTuWeThFrSaWeek
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$18,000
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$18,000
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$18,000
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$14,000
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 $10,000
September 2027
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$10,000
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 $10,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heat, Pool is heated to 82 degrees in July & August and included in rental rate.  Higher temperature upon request at additional charge. Please inquire!

Pool Heat, June & September. Pool heated to 82 additional $300 per week!

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CHOAY

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Property Details
Gorgeous Luxury Home, Edgartown, Heated Pool, Pickle Ball Court, Multiple Living Spaces, 4 Bedrooms. 4.5 Baths Sleeps 9.

This stunning contemporary vacation home in Edgartown offers an exceptional blend of indoor and outdoor living spaces, making it an ideal retreat for relaxation and entertainment. The beautifully landscaped yard features...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$12,000 - $23,000
June 2027
SuMoTuWeThFrSaWeek
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$12,000
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$12,000
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$13,000
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 $16,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$16,000
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$16,000
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$16,000
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$19,000
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$20,000
August 2027
SuMoTuWeThFrSaWeek
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$23,000
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$23,000
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$23,000
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$19,000
29
30
31
 $16,000
September 2027
SuMoTuWeThFrSaWeek
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$16,000
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$12,000
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$12,000
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29
30
 
Clean Fee: 
$1000 per week
Tax: State & Local: 
11.7

Pool Heat additional $250 per week June & September

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CLARA

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Property Details
Exclusive Makonikey Area Home, Private Landscaped Yard, Large Deck Area, 4 bedrooms & 4 Baths. Short Drive to Towns and Multiple Beaches

Family 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
Baths: 
4
Price Range:
$4,000 - $4,000
June 2027
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July 2027
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August 2027
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September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$700 per week
Tax: State & Local: 
11.7

Sheets & Towels are not provided. Rental guests need to bring sheets & towels, or they can be rented and delivered per the instructions from the linen rental company. www.marthaslinenrental.com

 

 

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CLARO

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Property Details
Contemporary Farmhouse Design, Multiple Living Areas, Screened Porch & Farmers Porch, Deck, Lovely Yard Area, Bike or Walk to Oak Bluffs Center.

Contemporary Farmhouse Design | Multiple Living Areas | Screened Porch, Farmer’s Porch & Deck | Walk or Bike to Oak Bluffs Center

Located just on the outskirts of Oak Bluffs,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$3,100 - $5,300
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$3,300
6
7
8
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10
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12
$3,300
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$3,600
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$4,300
27
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29
30
 $5,300
July 2027
SuMoTuWeThFrSaWeek
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2
3
$5,300
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$5,300
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$5,300
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$5,300
25
26
27
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29
30
31
$5,900
August 2027
SuMoTuWeThFrSaWeek
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2
3
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5
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7
$6,100
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9
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13
14
$6,100
15
16
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20
21
$5,900
22
23
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25
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27
28
$5,000
29
30
31
 $3,600
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,600
5
6
7
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10
11
$3,600
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13
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$3,100
19
20
21
22
23
24
25
$3,100
26
27
28
29
30
 
Clean Fee: 
$450 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 - $9,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,700
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
$8,100
27
28
29
30
 $8,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,500
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
16
17
$9,000
18
19
20
21
22
23
24
$9,500
25
26
27
28
29
30
31
$10,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,500
8
9
10
11
12
13
14
$10,500
15
16
17
18
19
20
21
$10,500
22
23
24
25
26
27
28
$10,000
29
30
31
 $6,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,000
5
6
7
8
9
10
11
$5,500
12
13
14
15
16
17
18
$5,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
 $4,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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CLEME

Inquire
Property Details
Sweetened Water Farm, 1 Mile from Village Center, Bike or Walk to Town

Lovely 4 bedroom, 2 bath home.  Located just on the outskirts of Edgartown village center on Sweetened Water Farm (an 87-acre horse farm located near Morning Glory Farm).  This spacious...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$2,500 - $6,200
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$2,500
6
7
8
9
10
11
12
$4,500
13
14
15
16
17
18
19
$4,500
20
21
22
23
24
25
26
$4,500
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
$5,500
25
26
27
28
29
30
31
$5,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$6,200
8
9
10
11
12
13
14
$6,200
15
16
17
18
19
20
21
$6,200
22
23
24
25
26
27
28
$6,200
29
30
31
 $4,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,000
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
 $3,000
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

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