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Gracious Village Area 5 Bedroom Home, Light Filled Interior, Mulitple Living Spaces, Large Landscaped Yard, Located on Quiet Side St, 5 min Walk to Main St.

Stunning Edgartown Village Home! This meticulously maintained and newly updated property offers multiple living areas, 5 bedrooms, and 3.5 baths, surrounded by a lushly landscaped yard. Just a 5-minute walk...Read more

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

 

Parking for 3 cars, no on street parking

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JOSEJ

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Property Details
Exquisite Coastal Style Home, Pool, Patio, Landscaped Yard! 10 minute walk to Oak Bluffs Center, Luxury Interior, 3 bedrooms, 4 baths, Multiple Living Spaces

This newly constructed, luxurious home offers the perfect blend of comfort, style, and convenience. Featuring a heated 16 x 32' pool with varying depths of 3 to 8 feet, a...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $14,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,000
6
7
8
9
10
11
12
$6,000
13
14
15
16
17
18
19
$6,000
20
21
22
23
24
25
26
$6,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,000
4
5
6
7
8
9
10
$12,000
11
12
13
14
15
16
17
$12,000
18
19
20
21
22
23
24
$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,500
8
9
10
11
12
13
14
$14,500
15
16
17
18
19
20
21
$14,500
22
23
24
25
26
27
28
$11,500
29
30
31
 $11,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$11,500
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 $6,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to  81 degrees included in rental rate last Sat in June to first Sat in September. Pool Depth 3 feet to 8 Feet 

Pool Heated to 81 degrees June and September weeks additional $275 per week  

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WESTW

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Property Details
Tri Level Oak Bluffs Home, Central A/C, Set in Private Community of Sengekontacket, Multiple Living Spaces, Large Deck, Patio Area, Association Tennis

Privately situated on a hilltop in Sengekontacket, -spacious tri-level, 4000 sq ft contemporary home. Set in a wonderful, family friendly community, offering association tennis courts, and an association dock on Sengekontacket Pond...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
5
Baths: 
2
Price Range:
$5,300 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $8,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,000
4
5
6
7
8
9
10
$8,500
11
12
13
14
15
16
17
$9,000
18
19
20
21
22
23
24
$10,000
25
26
27
28
29
30
31
$10,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,000
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
$12,000
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$5,300
19
20
21
22
23
24
25
$5,300
26
27
28
29
30
 $5,300
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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NAIDN

Inquire
Property Details
Stunning Luxury Home, Heated 18 x 42 Gunite Pool, Spectacular Yard & Patio Areas, Ideally Located with a 10 minute Walk to Village, 7 minute drive to South Beach

Contemporary, architect-designed coastal-style farmhouse, this luxurious vacation home will exceed your every expectation in amenity, quality, furnishings, and location. Situated in a distinctive enclave of eight luxury homes on 1-2...Read more

Location: 
Edgartown
Sleeps: 
9
Bedrooms: 
5
Baths: 
5
Price Range:
$14,000 - $14,000
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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21
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26
27
28
29
30
 
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner will rent June & July weeks of 2026 on a Fri to Fri basis available. 

 

Pool Heated to 81 degrees July & August, included in the rental rate. Pool Heated to 81 June & September,  additional $400 per week propane fee. 

 

 

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ZILLK

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Property Details
Newly Updated Contemporary Home, Heated Pool, Bluestone Patio, Spacious Deck, Tucked Away and Close to Long Point Beach.

Nestled in the town of West Tisbury, this exquisite contemporary residence boasts a heated pool, surrounded by a patio, and enveloped by lush landscaping, offering a private oasis for those seeking...Read more

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

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

Pool Heated to 81 in June & Sept additional $250 per week

Pool size is 20 x 40 

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KNOXA

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Property Details
Modern Cottage, Recently Updated! Walk to Oak Bluffs Harbor and Town Center, 15 min walk

Walk to Oak Bluffs town center, ferry, or Inkwell Beach from this beach-chic recently renovated, adorable cottage! 

Upon entering you are greeted with an open floor plan in the living, kitchen,...Read more

Location: 
Oak Bluffs
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$3,600 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$3,850
6
7
8
9
10
11
12
$3,850
13
14
15
16
17
18
19
$3,850
20
21
22
23
24
25
26
$3,850
27
28
29
30
 $4,200
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$4,200
4
5
6
7
8
9
10
$4,200
11
12
13
14
15
16
17
$4,200
18
19
20
21
22
23
24
$4,200
25
26
27
28
29
30
31
$4,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$5,800
8
9
10
11
12
13
14
$14,000
15
16
17
18
19
20
21
$14,000
22
23
24
25
26
27
28
$4,900
29
30
31
 $4,900
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$4,900
5
6
7
8
9
10
11
$3,850
12
13
14
15
16
17
18
$3,850
19
20
21
22
23
24
25
$3,850
26
27
28
29
30
 $3,600
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7

 

 

 

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WESTC

Inquire
Property Details
Summer Wind in the Heart of Oak Bluffs, Water views. 2 minute Walk to Inkwell Beach & 5 minute walk to town, All Newly Remodeled 5 Bedroom, 3 Bath Home With Deluxe Amenities

Set in the heart of Oak Bluffs center, this newly renovated home features water views, walk to Inkwell Beach and Pay Beach and walk to the town center all within...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $14,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$8,000
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$9,000
20
21
22
23
24
25
26
$10,000
27
28
29
30
 $12,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$12,000
4
5
6
7
8
9
10
$13,000
11
12
13
14
15
16
17
$14,000
18
19
20
21
22
23
24
$14,000
25
26
27
28
29
30
31
$15,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$22,000
8
9
10
11
12
13
14
$22,000
15
16
17
18
19
20
21
$22,000
22
23
24
25
26
27
28
$14,000
29
30
31
 $9,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,500
5
6
7
8
9
10
11
$8,000
12
13
14
15
16
17
18
$7,000
19
20
21
22
23
24
25
$7,000
26
27
28
29
30
 $7,000
Clean Fee: 
$550
Tax: State & Local: 
11.7
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HUN28

Inquire
Property Details
Lovely New 3 Bedroom, 3.5 Bath Home, 15 min walk to Oak Bluffs Center, Inkwell Beach and Town Beach, Sleeps 8, 3 Bedrooms, Plus Loft, 3.5 Baths

This stylish contemporary retreat is ideally located in a lovely, peaceful Oak Bluffs neighborhood, just a 10–15 minute stroll to the village center, parks, Inkwell Beach, Oak Bluffs Town Beach, and...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,250 - $13,960
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$9,760
6
7
8
9
10
11
12
$9,760
13
14
15
16
17
18
19
$9,760
20
21
22
23
24
25
26
$9,760
27
28
29
30
 $9,760
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,760
4
5
6
7
8
9
10
$10,460
11
12
13
14
15
16
17
$10,460
18
19
20
21
22
23
24
$10,460
25
26
27
28
29
30
31
$10,460
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,960
8
9
10
11
12
13
14
$13,960
15
16
17
18
19
20
21
$13,960
22
23
24
25
26
27
28
$13,960
29
30
31
 $13,960
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,960
5
6
7
8
9
10
11
$9,060
12
13
14
15
16
17
18
$6,650
19
20
21
22
23
24
25
$6,650
26
27
28
29
30
 $6,650
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

2026, Owner offers 10% discount off rental rate - May, June, July weeks for 7 night stay or longer. 

 

3 night minimum stay required, May, June to last week, September 5 on &, October. 

 

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PANDC

Inquire
Property Details
Coffin's Field, Main House, and Guest Apartment above Garage, Heated Pool - 16 x 32, Porch and Spacious Deck, 8 Minute Drive to Gorgeous Trustees / Long Point Beach

Lovely farmhouse-style 5-bedroom home with heated pool -16' x 32', 3 to 5 feet depth,  main house, and guest apartment over the garage centrally located and easily accessible to Long Point Beach and Edgartown...Read more

Location: 
Edgartown
Sleeps: 
12
Bedrooms: 
5
Baths: 
3
Price Range:
$6,000 - $13,900
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,500
6
7
8
9
10
11
12
$7,500
13
14
15
16
17
18
19
$8,950
20
21
22
23
24
25
26
$8,950
27
28
29
30
 $8,950
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,950
4
5
6
7
8
9
10
$11,300
11
12
13
14
15
16
17
$11,300
18
19
20
21
22
23
24
$11,300
25
26
27
28
29
30
31
$13,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,900
8
9
10
11
12
13
14
$13,900
15
16
17
18
19
20
21
$13,900
22
23
24
25
26
27
28
$11,300
29
30
31
 $8,950
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,950
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$7,500
19
20
21
22
23
24
25
$7,500
26
27
28
29
30
 $6,000
Clean Fee: 
$700
Tax: State & Local: 
11.7

Pool & the Spa in the pool heated to 81 degrees, included in Rental Rate, July & August Weeks. Spa not heated to higher temperatures, and jets will be off. 

 

Pool & Spa  Heated to 81 degrees, June & September weeks, additional charge per week.

 

No Pool & Spa before 5/28 and after 9/24

 

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CASED

Inquire
Property Details
Deep Bottom Pond, Private Heated Pool, Central Air, WiFi, Gorgeous Views

Contemporary home in the Deep Bottom area of West Tisbury. This gracious home with a pool and patio overlooks the open meadowland that is the Deep Bottom. The home is...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
5
Baths: 
4
Price Range:
$13,500 - $13,500
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
 $13,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$13,500
4
5
6
7
8
9
10
$13,500
11
12
13
14
15
16
17
$13,500
18
19
20
21
22
23
24
$13,500
25
26
27
28
29
30
31
$13,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$13,500
8
9
10
11
12
13
14
$13,500
15
16
17
18
19
20
21
$13,500
22
23
24
25
26
27
28
$13,500
29
30
31
 $13,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$13,500
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: 
$475 per week
Tax: State & Local: 
11.7

Pool Heated to 82 degrees mid June to mid Sept, pool heat costs included in rental rate.

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ROGLM

Inquire
Property Details
Coastal Contemporary Beach House, Newly updated! Located under a mile from South Beach & 2 miles from Edgartown Center.

Feel the south shore breezes at this great vacation home ideally located in the Katama area. The proximity to both South Beach and Edgartown village center makes this home an ideal choice...Read more

Location: 
Edgartown
Sleeps: 
10
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $13,500
June 2027
SuMoTuWeThFrSa
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July 2027
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August 2027
SuMoTuWeThFrSa
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September 2027
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Clean Fee: 
$600
Tax: State & Local: 
11.7
Add Favorite
 
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KILLY

Inquire
Property Details
Beautiful Village Area Summer Retreat, Tucked Away on a Quiet Street, Walk to Village Center.

This lovely contemporary home offers the perfect blend of elegance, comfort, and prime location in the highly sought-after Plantingfield Wood area of Edgartown. With its soothing coastal palette and modern design,...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,500 - $13,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
6
7
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10
11
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$11,000
13
14
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18
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$11,000
20
21
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$11,000
27
28
29
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 $10,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$10,500
4
5
6
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8
9
10
$11,000
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$11,000
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$11,000
25
26
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30
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$12,000
August 2027
SuMoTuWeThFrSaWeek
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2
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$13,000
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$13,000
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$13,000
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$12,000
29
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 $8,000
September 2027
SuMoTuWeThFrSaWeek
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2
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$8,000
5
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$7,500
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$6,000
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$5,500
26
27
28
29
30
 $5,500
Clean Fee: 
$300 per week
Tax: State & Local: 
11.7
Add Favorite
 
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MEINT

Inquire
Property Details
Stately Historic Chilmark Home, All Newly updated to Luxury Standards, Private Association South Shore Beach Rights, Hancock Beach 1.5 miles from House

This is an updated 5-bedroom, 3½ bath, farmhouse set back behind ancient Chilmark stonewalls with a key to Hancock Beach!  The house lies between West Tisbury (Alley’s General Store, 7A...Read more

Location: 
Chilmark
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$5,000 - $13,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$8,000
6
7
8
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10
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$8,000
13
14
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$8,000
20
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$8,000
27
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 $11,000
July 2027
SuMoTuWeThFrSaWeek
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2
3
$11,000
4
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$11,000
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$11,000
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$11,000
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$13,000
August 2027
SuMoTuWeThFrSaWeek
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$13,000
8
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$13,000
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$13,000
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$11,000
29
30
31
 $8,000
September 2027
SuMoTuWeThFrSaWeek
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2
3
4
$8,000
5
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$8,000
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$8,000
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$8,000
26
27
28
29
30
 $5,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BAKE7

Inquire
Property Details
Waterview, Walk to the Beach and Town Center, Impeccably Maintained 4 bedroom Home set in the Heart of Oak Bluffs.

This restored historic J.A. Norton Main and Guest Suite Quarters seamlessly blends 1870s character with the modern comforts today’s travelers appreciate. Nestled in a peaceful  Oak Bluffs neighborhood, the property is just...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $13,000
June 2027
SuMoTuWeThFrSaWeek
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2
3
4
5
$4,400
6
7
8
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$4,400
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$4,900
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$4,900
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 $6,000
July 2027
SuMoTuWeThFrSaWeek
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2
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$6,000
4
5
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$8,800
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$8,800
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19
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$8,900
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$9,000
August 2027
SuMoTuWeThFrSaWeek
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2
3
4
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$12,000
8
9
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$12,000
15
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$13,000
22
23
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$13,000
29
30
31
 $8,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,500
5
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7
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$5,600
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$5,600
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$5,600
26
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28
29
30
 $5,600
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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ROBDE

Inquire
Property Details
Edgartown, Katama Area, Spacious Luxury with Designer Detailing, Chef's Kitchen, Multiple Living Spaces, 4 Bedrooms, 3.5 Baths

New in 2022 large addition and full renovation to this beautiful Katama home. Located within walking distance of town (1.4 miles) and biking to Katama South Beach (2.1 miles). 

The...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$13,000 - $13,000
June 2027
SuMoTuWeThFrSa
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July 2027
SuMoTuWeThFrSa
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August 2027
SuMoTuWeThFrSaWeek
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$13,000
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$13,000
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$13,000
29
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31
 
September 2027
SuMoTuWeThFrSa
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Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

Sales Tax Exempt for weeks 8/8 & 8/15

 

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