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Gracious Village Area 5 Bedroom Home, Light Filled Interior, Multiple 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:
$10,000 - $10,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$10,000
6
7
8
9
10
11
12
$10,000
13
14
15
16
17
18
19
$10,000
20
21
22
23
24
25
26
$14,500
27
28
29
30
 $15,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$15,000
4
5
6
7
8
9
10
$15,000
11
12
13
14
15
16
17
$15,000
18
19
20
21
22
23
24
$15,000
25
26
27
28
29
30
31
$17,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$17,000
8
9
10
11
12
13
14
$17,000
15
16
17
18
19
20
21
$17,000
22
23
24
25
26
27
28
$15,000
29
30
31
 $12,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$12,500
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$10,000
19
20
21
22
23
24
25
$10,000
26
27
28
29
30
 $10,000
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

 

Parking for 3 cars, no on street parking

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Bridle Path House, Quiet Lovely Neighborhood, Porch and Deck Areas, Large Yard, Central Location to all 3 Down Island Towns and Beaches

Lovely 3 bedroom 3 bath home sleeps 8, bordered by a large landscaped yard. The exterior features a shady wrap-around porch with rockers, a perfect place to relax, read a book,  and enjoy...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
2
Price Range:
$8,000 - $9,800
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
$8,000
20
21
22
23
24
25
26
$8,000
27
28
29
30
 $9,800
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,800
4
5
6
7
8
9
10
$9,800
11
12
13
14
15
16
17
$9,800
18
19
20
21
22
23
24
$9,800
25
26
27
28
29
30
31
$9,800
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,800
8
9
10
11
12
13
14
$10,500
15
16
17
18
19
20
21
$11,500
22
23
24
25
26
27
28
$9,800
29
30
31
 $9,800
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,800
5
6
7
8
9
10
11
$9,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
 $8,000
Clean Fee: 
$350 per week
Tax: State & Local: 
14.45
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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 - $9,760
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: 
14.45

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

 

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Water view Upper Makonikey Home, Distinctive Design by Royal Barry Wills, Two Private Association Beaches, Central A/C

Classic Royal Barry Wills-designed cedar-shingled Vineyard home, beautifully sited on five private landscaped acres in the exclusive enclave of homes known as Makonikey. Lovely distant water views of Vineyard Sound and...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,000 - $9,750
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,000
6
7
8
9
10
11
12
$5,750
13
14
15
16
17
18
19
$5,750
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,750
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,750
4
5
6
7
8
9
10
$9,750
11
12
13
14
15
16
17
$9,750
18
19
20
21
22
23
24
$9,750
25
26
27
28
29
30
31
$9,750
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,750
8
9
10
11
12
13
14
$9,750
15
16
17
18
19
20
21
$9,750
22
23
24
25
26
27
28
$9,750
29
30
31
 $7,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,500
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$5,750
19
20
21
22
23
24
25
$5,750
26
27
28
29
30
 
Clean Fee: 
$350 per week
Tax: State & Local: 
11.7
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Spectacular Chilmark Sunset Water Views, Walk to Private Associaton Waterfont on the North Shore, Association Tennis and many Walking Trails.

This charming, updated cottage is located on Chilmark's iconic north shore with views of Vineyard Sound and the Elizabeth Islands.  Take in spectacular sunset water views from the 40-foot deck...Read more

Location: 
Chilmark
Sleeps: 
8
Bedrooms: 
4
Baths: 
2
Price Range:
$5,000 - $9,500
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
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
$5,500
27
28
29
30
 $5,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$5,500
4
5
6
7
8
9
10
$8,500
11
12
13
14
15
16
17
$8,500
18
19
20
21
22
23
24
$8,500
25
26
27
28
29
30
31
$8,500
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,500
8
9
10
11
12
13
14
$9,500
15
16
17
18
19
20
21
$9,500
22
23
24
25
26
27
28
$7,500
29
30
31
 $7,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,500
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
 $5,500
Clean Fee: 
$475 per week
Tax: State & Local: 
11.7

This home books Fri to Fri in July & August

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Gorgeous Retreat, Pool 18 X 36', Lush Landscaped Yard, Expansive Deck & Patio Areas, Luxury Interior, Media Room, Lambert's Cove Beach 1/2 mile

Gather your family, this gorgeous 5 bedroom home offers all one could want in a vacation home on the Vineyard. Resort-like outdoor amenities include a pool, stone patio surround, large deck with...Read more

Location: 
West Tisbury
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$8,700 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,100
6
7
8
9
10
11
12
$7,100
13
14
15
16
17
18
19
$7,100
20
21
22
23
24
25
26
$7,900
27
28
29
30
 $8,700
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,700
4
5
6
7
8
9
10
$8,700
11
12
13
14
15
16
17
$8,700
18
19
20
21
22
23
24
$9,400
25
26
27
28
29
30
31
$9,400
August 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
31
 $6,600
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,600
5
6
7
8
9
10
11
$6,600
12
13
14
15
16
17
18
$6,600
19
20
21
22
23
24
25
$6,600
26
27
28
29
30
 
Clean Fee: 
$700 per week
Tax: State & Local: 
11.7
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Katama Area, Stylish Designer Luxury, Bike to South Beach and Village Areas, Spacious Bluestone Patio overlooks Private Yard Area

All newly renovated and beautifully furnished, the main level of this traditional style floor plan includes, - hardwood floors throughout, bead board accents, a living room with balcony, TV center,...Read more

Location: 
Katama
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,000 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$6,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$9,400
27
28
29
30
 $9,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,400
4
5
6
7
8
9
10
$9,400
11
12
13
14
15
16
17
$9,400
18
19
20
21
22
23
24
$9,400
25
26
27
28
29
30
31
$9,400
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,400
8
9
10
11
12
13
14
$9,400
15
16
17
18
19
20
21
$9,400
22
23
24
25
26
27
28
$9,400
29
30
31
 $9,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,400
5
6
7
8
9
10
11
$5,900
12
13
14
15
16
17
18
$4,900
19
20
21
22
23
24
25
$4,900
26
27
28
29
30
 $4,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Owner maintains a 2 week minimum stay from mid-June to 2nd week in September.

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Newly Remodeled Contemporary Farm House, 12 x 26 Saltwater Heated Pool, Walk to Town, Bike to the Beach

Exquisite newly remodeled home with just the right touch of coastal decor and modern styling. This perfectly situated picturesque home allows guests to walk to the village area and is an easy no...Read more

Location: 
Katama
Sleeps: 
7
Bedrooms: 
3
Baths: 
2
Price Range:
$4,200 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,450
6
7
8
9
10
11
12
$6,800
13
14
15
16
17
18
19
$6,800
20
21
22
23
24
25
26
$9,400
27
28
29
30
 $9,400
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,400
4
5
6
7
8
9
10
$9,700
11
12
13
14
15
16
17
$10,200
18
19
20
21
22
23
24
$10,200
25
26
27
28
29
30
31
$10,650
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$10,650
8
9
10
11
12
13
14
$10,650
15
16
17
18
19
20
21
$10,650
22
23
24
25
26
27
28
$7,800
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$6,000
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
 $4,200
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Pool heated to 81 in July & August included in rental rate.  Additional $250 per week in off season.

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Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,900 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$7,100
13
14
15
16
17
18
19
$7,700
20
21
22
23
24
25
26
$8,400
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
4
5
6
7
8
9
10
$9,000
11
12
13
14
15
16
17
$9,400
18
19
20
21
22
23
24
$9,700
25
26
27
28
29
30
31
$9,900
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$11,200
8
9
10
11
12
13
14
$11,700
15
16
17
18
19
20
21
$11,200
22
23
24
25
26
27
28
$10,000
29
30
31
 $8,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$8,400
5
6
7
8
9
10
11
$7,000
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
 $4,500
Clean Fee: 
$500 per week
Tax: State & Local: 
14.45

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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Outstanding 4 Bedrom, 4 Bath Home, Located in Deep Bottom Community of Homes, Association Tennis, Gorgeous Views across Pasture and Pond

Note: New for 2027, Lower Level, will have 4th Bedroom, Bath, Media Area & Office. Will be professionally decorated in keeping with the decor of the house. 

 

 ...Read more

Location: 
West Tisbury
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,400 - $9,400
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$7,900
6
7
8
9
10
11
12
$7,900
13
14
15
16
17
18
19
$8,400
20
21
22
23
24
25
26
$8,400
27
28
29
30
 $8,900
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$8,900
4
5
6
7
8
9
10
$8,900
11
12
13
14
15
16
17
$8,900
18
19
20
21
22
23
24
$9,400
25
26
27
28
29
30
31
$9,400
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,400
8
9
10
11
12
13
14
$9,400
15
16
17
18
19
20
21
$9,400
22
23
24
25
26
27
28
$9,400
29
30
31
 $9,400
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,400
5
6
7
8
9
10
11
$8,900
12
13
14
15
16
17
18
$8,900
19
20
21
22
23
24
25
$8,900
26
27
28
29
30
 $6,400
Clean Fee: 
Tax: State & Local: 
11.7
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Lovely Historic William St Home, Located just one block from Main St. 4 bedrooms, 4 baths

Beautifully renovated Greek Revival home (the Berkshire House) on historic William Street in Vineyard Haven.

This finely crafted home offers vacationing guests spacious living on three levels. The main level...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,900 - $9,250
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
$7,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,250
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,250
4
5
6
7
8
9
10
$9,250
11
12
13
14
15
16
17
$9,250
18
19
20
21
22
23
24
$9,250
25
26
27
28
29
30
31
$9,250
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,250
8
9
10
11
12
13
14
$9,250
15
16
17
18
19
20
21
$9,250
22
23
24
25
26
27
28
$9,250
29
30
31
 
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
$6,900
12
13
14
15
16
17
18
$6,900
19
20
21
22
23
24
25
$5,900
26
27
28
29
30
 $5,900
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

 

 

 

 

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Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$9,000 - $9,000
June 2027
SuMoTuWeThFrSa
 1
2
3
4
5
6
7
8
9
10
11
12
13
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15
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20
21
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25
26
27
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29
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July 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
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13
14
15
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17
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19
20
21
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23
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$12,000
25
26
27
28
29
30
31
$12,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$14,000
8
9
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14
$14,000
15
16
17
18
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20
21
$14,000
22
23
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25
26
27
28
$12,000
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
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$9,000
5
6
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12
13
14
15
16
17
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19
20
21
22
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24
25
26
27
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29
30
 
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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Quintessential Vineyard Haven Home, Beautifully Furnished, Surrounded by Large Mature Landscaped Yard, Porch Seating, Multiple Living Spaces Within

Classic Vineyard home set on a quiet street of similar homes. Modern interior with multiple living spaces include a large family room centered around the media area with a sectional sofa...Read more

Location: 
Vineyard Haven
Sleeps: 
7
Bedrooms: 
4
Baths: 
2
Price Range:
$6,000 - $9,000
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
 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,500
4
5
6
7
8
9
10
$7,150
11
12
13
14
15
16
17
$8,000
18
19
20
21
22
23
24
$8,000
25
26
27
28
29
30
31
$9,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,000
8
9
10
11
12
13
14
$9,000
15
16
17
18
19
20
21
$9,000
22
23
24
25
26
27
28
$8,000
29
30
31
 $6,500
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$6,500
5
6
7
8
9
10
11
$6,500
12
13
14
15
16
17
18
$6,000
19
20
21
22
23
24
25
$6,000
26
27
28
29
30
 
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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La Mar, A Lovely Reverse Beach House in the Long Point Area, Newly updated, Spacious Decks, 2 Screened Porches, Sleeps 8

La Mar is a Beautifully Renovated 4-Bedroom Home with expansive outdoor living spaces on the upper and lower level decks, and screened porches on the 2nd level and off the lower level bedrooms....Read more

Location: 
West Tisbury
Sleeps: 
7
Bedrooms: 
4
Baths: 
3
Price Range:
$5,000 - $9,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$5,500
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
$7,000
27
28
29
30
 $7,500
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$7,500
4
5
6
7
8
9
10
$8,000
11
12
13
14
15
16
17
$8,000
18
19
20
21
22
23
24
$8,500
25
26
27
28
29
30
31
$9,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$9,300
8
9
10
11
12
13
14
$9,300
15
16
17
18
19
20
21
$9,300
22
23
24
25
26
27
28
$8,500
29
30
31
 
September 2027
SuMoTuWeThFrSa
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2
3
4
5
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8
9
10
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12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
Clean Fee: 
$525 per week
Tax: State & Local: 
11.7
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Oak Bluffs Vacation Retreat – Exceptional Craftsmanship, Thoughtful Design & Unmatched Comfort, Sleeps 8

Custom crafted with extraordinary attention to detail, quality, and comfort, this stunning Oak Bluffs vacation home offers an exceptional island getaway. Nestled in a peaceful residential neighborhood just two miles...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$5,000 - $9,000
June 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$6,500
20
21
22
23
24
25
26
$7,500
27
28
29
30
 $9,000
July 2027
SuMoTuWeThFrSaWeek
 1
2
3
$9,000
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
$9,000
25
26
27
28
29
30
31
$11,000
August 2027
SuMoTuWeThFrSaWeek
1
2
3
4
5
6
7
$12,000
8
9
10
11
12
13
14
$12,000
15
16
17
18
19
20
21
$12,000
22
23
24
25
26
27
28
$10,000
29
30
31
 $9,000
September 2027
SuMoTuWeThFrSaWeek
 1
2
3
4
$9,000
5
6
7
8
9
10
11
$7,500
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$5,500
26
27
28
29
30
 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
14.45

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