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
Spacious Oak Bluffs Contemporary Home, 4 Bedrooms & 4 Baths, Quiet Private Location in Bayes Hill Community of Homes
Privately situated on the outskirts of Oak Bluffs, yet centrally located to towns and beaches. The home features a large patio area with outdoor dining and grill area and a spacious...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
4
Price Range:
$3,500 - $7,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,800
27
28
29
30
$4,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$4,500
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
$6,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$7,000
8
9
10
11
12
13
14
$7,000
15
16
17
18
19
20
21
$7,000
22
23
24
25
26
27
28
$5,500
29
30
31
$4,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,000
5
6
7
8
9
10
11
$4,000
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
$3,500
Clean Fee:
$575
Tax: State & Local:
11.7
Rates reduced for available weeks June - September - see calendar for adjusted rates
Stylish Main & Guest House with Heated Pool, 10 x 16 Plunge Pool,Landscaped Yard, Walk to Village Center, Sleeps 8-10 2026- Owner will rent Main House Only in June for $10,000 per week, and $15,000 open July weeks.Inquire for Details!
This inviting 5-bedroom, 3.5-bath compound is perfect for extended families and friends. It features a Main House and separate Guest House, both offering a heated plunge pool, 10 x 16...Read more
Location:
Edgartown
Sleeps:
9
Bedrooms:
5
Baths:
3
Price Range:
$15,000 - $20,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$18,000
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$18,000
4
5
6
7
8
9
10
$20,000
11
12
13
14
15
16
17
$18,000
18
19
20
21
22
23
24
$18,000
25
26
27
28
29
30
31
$18,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$20,000
8
9
10
11
12
13
14
$20,000
15
16
17
18
19
20
21
$20,000
22
23
24
25
26
27
28
$15,000
29
30
31
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
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:
$750 per week
Tax: State & Local:
11.7
Pool Heated to 82 included in rental rate July & August weeks.
Pool Heated to 82 June & September weeks additional $275 per week propane surcharge.
Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths
Tucked just beyond the heart of downtown Oak Bluffs, this spacious, architect-designed retreat offers families and friends an exceptional Vineyard vacation experience.
Thoughtfully crafted by a noted architect, the home...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$8,500 - $20,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$8,500
6
7
8
9
10
11
12
$8,500
13
14
15
16
17
18
19
$11,000
20
21
22
23
24
25
26
$14,000
27
28
29
30
$16,500
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$16,500
4
5
6
7
8
9
10
$16,500
11
12
13
14
15
16
17
$18,000
18
19
20
21
22
23
24
$18,000
25
26
27
28
29
30
31
$20,000
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$20,000
8
9
10
11
12
13
14
$21,000
15
16
17
18
19
20
21
$21,500
22
23
24
25
26
27
28
$18,000
29
30
31
$10,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$10,000
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
$9,000
26
27
28
29
30
$9,000
Clean Fee:
$600 per week
Tax: State & Local:
11.7
1st Two Weeks of July 2026 being offered at $16,500 per week
Pool Heated to 81 degrees July & August included in Rental Rate
Pool Heated to 81 degrees June & September additional $300 Propane Surcharge
Lovely, Recently Updated West Chop Area Home, Spacious Deck, Open Living Spaces, 15 Minute Walk to Town
This lovely, spacious, airy home was recently renovated, an open-concept home filled with natural light and located on a private road. Your next “home away from home” is perfectly located minutes from all...Read more
Location:
Vineyard Haven
Sleeps:
6
Bedrooms:
3
Baths:
2
Price Range:
$3,500 - $5,500
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$3,500
6
7
8
9
10
11
12
$3,500
13
14
15
16
17
18
19
$3,500
20
21
22
23
24
25
26
$3,800
27
28
29
30
$4,300
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$4,300
4
5
6
7
8
9
10
$4,300
11
12
13
14
15
16
17
$4,300
18
19
20
21
22
23
24
$4,800
25
26
27
28
29
30
31
$5,500
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$5,500
8
9
10
11
12
13
14
$5,800
15
16
17
18
19
20
21
$4,800
22
23
24
25
26
27
28
$4,400
29
30
31
$3,500
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$3,500
5
6
7
8
9
10
11
$3,500
12
13
14
15
16
17
18
$3,500
19
20
21
22
23
24
25
$3,500
26
27
28
29
30
$3,500
Clean Fee:
$450 per week
Tax: State & Local:
11.7
Rates reduced for available weeks in July & August - see calendar for adjusted rates
Perfect Retreat for Large Families, 1.5 miles to Oak Bluffs Town Center & Beach, Bike Path at end of Street
Spacious and perfect for extended families, featuring multiple attractively furnished living areas, and sleeps 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with...Read more
Location:
Oak Bluffs
Sleeps:
11
Bedrooms:
5
Baths:
3
Price Range:
$7,950 - $7,950
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
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 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
$7,950
25
26
27
28
29
30
31
$7,950
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$7,950
8
9
10
11
12
13
14
$7,950
15
16
17
18
19
20
21
$7,950
22
23
24
25
26
27
28
$7,950
29
30
31
$7,950
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$7,950
5
6
7
8
9
10
11
$7,950
12
13
14
15
16
17
18
$7,950
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
$7,950
Clean Fee:
$450 per week
Tax: State & Local:
11.7
Owner reduced rates for weeks 7/12 & 8/23 by 20% - see calendar for adjusted rate
Meadow House, 5 Minute Drive to Lambert's Cove Beach, Sleeps 6, AC, Private, Quiet Location yet close to Town and Beach, AC
Immaculately clean cabinesque home, privately located off of Lambert's Cove Rd, yet just a 5-minute drive to beautiful Lambert's Cove Beach and 10 minutes from Vineyard Haven town center.
Outstanding In-town Home, Gorgeous Professionally Landscaped Yard, 5 Min walk to Main Street Shops & Restaurants
Located on a quiet street in the Edgartown Village area, this lovely 5 bedroom, 3 bath Home has been all newly updated. The home is bordered by lush lawn, privacy fencing...Read more
Location:
Edgartown
Sleeps:
9
Bedrooms:
5
Baths:
3
Price Range:
$7,000 - $16,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,000
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
$9,000
27
28
29
30
$10,000
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$10,000
4
5
6
7
8
9
10
$12,500
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
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$13,000
8
9
10
11
12
13
14
$16,000
15
16
17
18
19
20
21
$16,000
22
23
24
25
26
27
28
$12,000
29
30
31
$11,000
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$11,000
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
Owner reduced rates for available weeks June, July & August - see calendar for adjusted rates
Exquisite all Newly Updated Contemporary Farm House Style Home! Heated Pool! Location!! 15 minute walk to Edgartown Village Center, 5 minute Drive to South Beach
Outstanding Edgartown Vacation Home! Walk or bike to the center of Edgartown Village from this handsomely crafted, 5-bedroom, 3.5-bath vacation home. Multiple living spaces flow seamlessly from inside to the vaulted, 3-season screened...Read more
Location:
Edgartown
Sleeps:
10
Bedrooms:
5
Baths:
3
Price Range:
$6,980 - $17,970
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$10,970
6
7
8
9
10
11
12
$10,970
13
14
15
16
17
18
19
$14,980
20
21
22
23
24
25
26
$14,980
27
28
29
30
$16,970
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$16,970
4
5
6
7
8
9
10
$16,970
11
12
13
14
15
16
17
$16,970
18
19
20
21
22
23
24
$16,970
25
26
27
28
29
30
31
$16,970
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$17,970
8
9
10
11
12
13
14
$17,970
15
16
17
18
19
20
21
$17,970
22
23
24
25
26
27
28
$17,970
29
30
31
$13,980
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$13,980
5
6
7
8
9
10
11
$10,970
12
13
14
15
16
17
18
$10,970
19
20
21
22
23
24
25
$10,970
26
27
28
29
30
$8,980
Clean Fee:
$475 per week
Tax: State & Local:
11.7
Owner reduced rates for 8/23, 8/30, and 9/6 weeks - see calendar for adjusted rates
Pool Heat to 82 degrees,included in rental rate July & August
Pool Heat to 82 degrees, Shoulder season weeks additional $250 per week
Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Multiple Living Spaces, Screened Porch, Spacious Deck, AC, Wifi, Beautifully Furnished, Bike Paths at the head of the Road
Spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. . The main living level features an open concept and hosts a family...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$4,700 - $5,000
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
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 2027
Su
Mo
Tu
We
Th
Fr
Sa
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
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
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
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
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:
$500 per week ($375 for interim cleaning on multiple week rentals)
Upscale Designer Interior, Features 3 Living Spaces, Pool Table, Ping Pong Table, Large Deck, Central A/C, WiFi, Conveniently Located to Towns and Beaches
Beautifully renovated large cape, centrally located in the desirable community of Dodger's Hole. This lovely 4 bedroom home features a large custom kitchen with upscale appliances and breakfast bar, an...Read more
Water Views, Heated Pool , Walk/Drive to Private Association Makonikey Beach, North Shore, Breathtaking Sunsets, Sleeps 8.
Looking to escape? This pristine contemporary home has it all; beautiful distant ocean views, a heated pool, a gorgeous pool house, patio dining and grill area poolside with an expansive deck the full width of...Read more
Location:
West Tisbury
Sleeps:
8
Bedrooms:
5
Baths:
4
Price Range:
$9,500 - $14,750
June 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$14,750
6
7
8
9
10
11
12
$14,750
13
14
15
16
17
18
19
$14,750
20
21
22
23
24
25
26
$14,750
27
28
29
30
$14,750
July 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
$14,750
4
5
6
7
8
9
10
$14,750
11
12
13
14
15
16
17
$14,750
18
19
20
21
22
23
24
$14,750
25
26
27
28
29
30
31
$14,750
August 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
$14,750
8
9
10
11
12
13
14
$14,750
15
16
17
18
19
20
21
$14,750
22
23
24
25
26
27
28
$14,750
29
30
31
$14,750
September 2027
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$14,750
5
6
7
8
9
10
11
$14,750
12
13
14
15
16
17
18
$14,750
19
20
21
22
23
24
25
$14,750
26
27
28
29
30
$14,750
Clean Fee:
$750 per week
Tax: State & Local:
11.7
Pool Heated to 81, included in Rental Rate last Saturday in June to end of August
Pool Heated to 81 June, and September weeks ( begins last Saturday in August), additional $300 propane surcharge per week
Special Offers from Owner:
June 13 - 20 - price reduced to $12,000
August 22nd - 9/5 2 Week stay for $28,000 instead of $29,500
