Quintessential Edgartown Village Home, Impeccably Maintained, 3 Minute Walk to Main St, 8 Minute Walk to Lighthouse Beach & the Harborfront Area
Charming Historic Home in the Heart of Edgartown Village
Built in 1780 and thoughtfully updated, this beautifully maintained historic home blends timeless character with modern comforts. Ideally located in the...Read more
Location:
Edgartown
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$5,500 - $11,900
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$7,000
14
15
16
17
18
19
20
$12,000
21
22
23
24
25
26
27
$12,000
28
29
30
$11,900
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$11,900
5
6
7
8
9
10
11
$11,900
12
13
14
15
16
17
18
$11,900
19
20
21
22
23
24
25
$11,900
26
27
28
29
30
31
$11,900
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$11,900
2
3
4
5
6
7
8
$11,900
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$11,900
23
24
25
26
27
28
29
$11,900
30
31
$9,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$9,000
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$5,500
27
28
29
30
$5,500
Clean Fee:
$500
Tax: State & Local:
11.7
Ferry tickets available for purchase, 7/19-7/26, & 7/26-8/2 - please inquire (mv)
Owner offers a 5% discount on the Rental Rate for two weeks, and 10% for 3 weeks or longer
Captain Swain House, Elegant Main & Guest House, 4 Bedrooms, 4.5 Baths, Multiple Indoor/Outdoor Living Spaces, 5 Minute Walk to Town, Expansive Landscaped Yard
In-Town Vacation Retreat in the William Street Historic District Just a five-minute walk to the heart of town, this spacious and beautifully updated home blends modern comfort with timeless...Read more
Location:
Vineyard Haven
Sleeps:
10
Bedrooms:
4
Baths:
4
Price Range:
$5,500 - $5,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$5,500
14
15
16
17
18
19
20
$5,500
21
22
23
24
25
26
27
$6,000
28
29
30
$5,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$5,500
5
6
7
8
9
10
11
$8,500
12
13
14
15
16
17
18
$8,500
19
20
21
22
23
24
25
$8,500
26
27
28
29
30
31
$8,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$8,500
2
3
4
5
6
7
8
$10,000
9
10
11
12
13
14
15
$10,000
16
17
18
19
20
21
22
$10,000
23
24
25
26
27
28
29
$10,000
30
31
$7,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,000
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
$6,000
Clean Fee:
$875 per week
Tax: State & Local:
11.7
Rate reduced for week 6/27 - 7/4 - see calendar for adjusted rate
Gorgeous Waterfront Home on the Lagoon, Newly Renovated, 4 bedrooms, 3.5 Baths, Spectacular Waterviews, Upper & Lower Decks
Waterfront Retreat on the Lagoon – Oak Bluffs
This beautifully renovated waterfront home offers breathtaking views, a private sandy beach on the Lagoon, and a stylish, coastal-inspired interior. Nearly every room...Read more
Owner offering 15% off all remaining weeks open 2026! Victorian East Chop Cottage all Newly updated, 4 Bedrooms, 3.5 Baths, Main House and Detached Guest Suite
Nestled in the highly sought-after East Chop neighborhood of Oak Bluffs, this charming Victorian cottage offers the perfect blend of classic Vineyard character and modern comfort. Ideally located within walking...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$4,000 - $11,480
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$6,200
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$8,500
28
29
30
$9,600
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$9,600
5
6
7
8
9
10
11
$10,000
12
13
14
15
16
17
18
$9,000
19
20
21
22
23
24
25
$9,000
26
27
28
29
30
31
$10,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$10,000
2
3
4
5
6
7
8
$11,480
9
10
11
12
13
14
15
$15,170
16
17
18
19
20
21
22
$14,030
23
24
25
26
27
28
29
$9,600
30
31
$8,920
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$8,920
6
7
8
9
10
11
12
$7,000
13
14
15
16
17
18
19
$5,500
20
21
22
23
24
25
26
$5,500
27
28
29
30
$4,000
Clean Fee:
$500 per week
Tax: State & Local:
11.7
Ferry Tickets available for purchase 7/18 to 7/25 & 8/1 to 8/8 weeks. Owner offering 15% off all weeks remaining open in 2026!
Owners are also open to weekday arrival and departure to accommodate the need for auto ferry ticket reservations.
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 - $4,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,800
28
29
30
$4,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,500
5
6
7
8
9
10
11
$4,500
12
13
14
15
16
17
18
$4,500
19
20
21
22
23
24
25
$4,500
26
27
28
29
30
31
$6,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$6,000
2
3
4
5
6
7
8
$7,000
9
10
11
12
13
14
15
$7,000
16
17
18
19
20
21
22
$7,000
23
24
25
26
27
28
29
$5,500
30
31
$4,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$4,000
6
7
8
9
10
11
12
$4,000
13
14
15
16
17
18
19
$4,000
20
21
22
23
24
25
26
$4,000
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 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$15,000
14
15
16
17
18
19
20
$15,000
21
22
23
24
25
26
27
$15,000
28
29
30
$18,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$18,000
5
6
7
8
9
10
11
$20,000
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
$18,000
26
27
28
29
30
31
$18,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$18,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$20,000
16
17
18
19
20
21
22
$20,000
23
24
25
26
27
28
29
$15,000
30
31
$15,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$15,000
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$15,000
20
21
22
23
24
25
26
$15,000
27
28
29
30
$15,000
Clean Fee:
$700 per week
Tax: State & Local:
11.7
Owner will rent main house only for $14,000 per week plus fees. There would be no one in the guest house during renter stay! Inquire for details!
Ferry Tickets available for transfer 7/4 - 7/11, 7/11- 7/18, (mv) Inquire for details
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:
$9,000 - $10,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$8,500
14
15
16
17
18
19
20
$11,000
21
22
23
24
25
26
27
$14,000
28
29
30
$16,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$16,500
5
6
7
8
9
10
11
$16,500
12
13
14
15
16
17
18
$18,000
19
20
21
22
23
24
25
$18,000
26
27
28
29
30
31
$20,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$20,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$21,000
16
17
18
19
20
21
22
$21,500
23
24
25
26
27
28
29
$18,000
30
31
$10,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
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
$9,000
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 - $4,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$3,500
14
15
16
17
18
19
20
$3,500
21
22
23
24
25
26
27
$3,800
28
29
30
$4,300
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$4,300
5
6
7
8
9
10
11
$4,300
12
13
14
15
16
17
18
$4,000
19
20
21
22
23
24
25
$4,000
26
27
28
29
30
31
$5,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$5,500
2
3
4
5
6
7
8
$4,500
9
10
11
12
13
14
15
$5,800
16
17
18
19
20
21
22
$4,800
23
24
25
26
27
28
29
$4,000
30
31
$3,500
September 2026
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
$3,500
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
Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Heated Pool, Spacious Stone Patio, Pool Pavilion, Propane Fire Pit, Professionally Landscaped Grounds and Gardens
Tucked on 7.25 private acres in the coveted seaside community of Chilmark, this exceptional retreat includes coveted access to Quansoo Beach—one of Martha’s Vineyard’s most stunning and private association shorelines. Offering...Read more
Location:
Chilmark
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$15,000 - $18,500
June 2026
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
$22,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$22,500
5
6
7
8
9
10
11
$22,500
12
13
14
15
16
17
18
$22,500
19
20
21
22
23
24
25
$22,500
26
27
28
29
30
31
$25,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$25,000
2
3
4
5
6
7
8
$20,000
9
10
11
12
13
14
15
$25,000
16
17
18
19
20
21
22
$18,000
23
24
25
26
27
28
29
$18,000
30
31
$18,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$18,000
6
7
8
9
10
11
12
$15,000
13
14
15
16
17
18
19
$18,500
20
21
22
23
24
25
26
27
28
29
30
Clean Fee:
$850 per week ($650 interim clean)
Tax: State & Local:
11.7
Rates reduced for available weeks in August - see calendar for adjusted rates
Ferry tickets available for purchase, 8/1-8/8 or 8/2 -8/9 - please inquire (mv)
Pool will be heated to 82 degrees July and August included in rental rate.
Pool Heated to 82 degrees June & Sept weeks $300/week
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:
$0 - $0
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$7,950
14
15
16
17
18
19
20
$7,950
21
22
23
24
25
26
27
$7,950
28
29
30
$7,950
July 2026
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
$6,360
19
20
21
22
23
24
25
$7,950
26
27
28
29
30
31
$7,950
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$7,950
2
3
4
5
6
7
8
$7,950
9
10
11
12
13
14
15
$7,950
16
17
18
19
20
21
22
$7,950
23
24
25
26
27
28
29
$6,360
30
31
$7,950
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$7,950
6
7
8
9
10
11
12
$7,950
13
14
15
16
17
18
19
$7,950
20
21
22
23
24
25
26
$7,950
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 - $15,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$8,000
14
15
16
17
18
19
20
$7,000
21
22
23
24
25
26
27
$7,500
28
29
30
$12,500
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$12,500
5
6
7
8
9
10
11
$10,500
12
13
14
15
16
17
18
$11,000
19
20
21
22
23
24
25
$11,000
26
27
28
29
30
31
$11,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$11,000
2
3
4
5
6
7
8
$13,000
9
10
11
12
13
14
15
$13,000
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$9,000
30
31
$10,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$10,000
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
$8,000
Clean Fee:
$600 per week
Tax: State & Local:
11.7
Owner reduced rates for available weeks June, July & August - see calendar for adjusted rates
Free Ferry Tickets Available for weeks 7/26-8/2, 8/23-8/30, 8/30-9/6 - please inquire
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 - $12,980
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$10,970
14
15
16
17
18
19
20
$14,980
21
22
23
24
25
26
27
$14,980
28
29
30
$16,970
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$16,970
5
6
7
8
9
10
11
$16,970
12
13
14
15
16
17
18
$16,970
19
20
21
22
23
24
25
$16,970
26
27
28
29
30
31
$16,970
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$16,970
2
3
4
5
6
7
8
$16,970
9
10
11
12
13
14
15
$16,970
16
17
18
19
20
21
22
$17,970
23
24
25
26
27
28
29
$16,480
30
31
$12,980
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$12,980
6
7
8
9
10
11
12
$10,970
13
14
15
16
17
18
19
$10,970
20
21
22
23
24
25
26
$10,970
27
28
29
30
$8,980
Clean Fee:
$475 per week
Tax: State & Local:
11.7
Owner reduced rates for 8/23 week & 8/30 week - 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 - $5,400
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
7
8
9
10
11
12
13
$5,400
14
15
16
17
18
19
20
$5,400
21
22
23
24
25
26
27
$5,400
28
29
30
$6,300
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$6,300
5
6
7
8
9
10
11
$6,300
12
13
14
15
16
17
18
$6,500
19
20
21
22
23
24
25
$6,700
26
27
28
29
30
31
$6,900
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$6,900
2
3
4
5
6
7
8
$9,100
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$9,500
23
24
25
26
27
28
29
$6,900
30
31
$6,600
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,600
6
7
8
9
10
11
12
$5,900
13
14
15
16
17
18
19
$5,000
20
21
22
23
24
25
26
$5,000
27
28
29
30
$5,000
Clean Fee:
$500 per week ($375 for interim cleaning on multiple week rentals)
