Classic updated 7 bedrooms, 5 bath West Chop Home. Nestled on a large landscaped lot on Hatch Rd in Vineyard Haven this spacious home offers the best in vacation home...Read more
Exceptional Main & Guest House, 20 x 40 Heated Pool with Stone Patio Surround, Tucked on Large Landscaped Acreage, 2 miles to Beautiful Lambert's Cove Beach, Sleeps 8
This exceptional vacation home and guest house have been recently updated, offering a large, heated saltwater pool nestled on expansive, private acreage in the desirable Indian Hill area of West...Read more
Location:
West Tisbury
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$11,500 - $15,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$11,500
7
8
9
10
11
12
13
$11,500
14
15
16
17
18
19
20
$11,500
21
22
23
24
25
26
27
$11,500
28
29
30
$12,900
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$12,900
5
6
7
8
9
10
11
$12,900
12
13
14
15
16
17
18
$12,900
19
20
21
22
23
24
25
$12,900
26
27
28
29
30
31
$14,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$14,000
2
3
4
5
6
7
8
$15,000
9
10
11
12
13
14
15
$15,000
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$15,000
30
31
September 2026
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:
$700 per week
Tax: State & Local:
11.7
Pool Heated to 82 degrees included in rental rate July & August
Pool Heated to 82 degrees, June, Sept & October additional $300 propane surcharge per week.
Requests for pool heated above 82 additional cost. Please inquire with an agent for details.
Water Views, Heated Pool , Walk/Drive to Private Association Waterfront, 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:
$10,000 - $14,750
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$14,750
7
8
9
10
11
12
13
$14,750
14
15
16
17
18
19
20
$14,750
21
22
23
24
25
26
27
$14,750
28
29
30
$14,750
July 2026
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
31
$14,750
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$14,750
2
3
4
5
6
7
8
$14,750
9
10
11
12
13
14
15
$14,750
16
17
18
19
20
21
22
$14,750
23
24
25
26
27
28
29
$14,750
30
31
$14,750
September 2026
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
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
Outstanding Waterfront Home, Private Dock, Spectacular Views & Sunsets across and up the Lagoon. Screened Porch, Larger Wrap Around Deck with Cushioned Chaise and Chair Seating
Nestled hillside, this lovely contemporary residence offers an exquisite retreat overlooking the tranquil lagoon and the sunsets are magnificent. Featuring breathtaking water vistas, a private dock, a screened porch, an expansive...Read more
Luxury Modern Farm House Design, Waterfront Pear Tree Cove on the Tisbury Great Pond, Rental Boat Access to South Shore Beach, Spectacular Area for Kayak Enthusiasts
New exquisite contemporary farmhouse design! Waterfront on the Tisbury Great Pond with access via boat rentals to gorgeous South Shore Beach. The beach area on the pond provides a great play space...Read more
Spacious Oak Bluffs Home, Heated Pool 16 x 32, 4 bedrooms & 3.5 baths sleeps 8
This charming and spacious 4-bedroom, 3.5-bath home offers multiple living areas, including a main living room with TV, a cozy sitting room, and a lower-level family room featuring a TV,...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
4
Baths:
3
Price Range:
$14,000 - $14,000
June 2026
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 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
31
$14,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$14,000
2
3
4
5
6
7
8
$14,000
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$14,000
23
24
25
26
27
28
29
30
31
September 2026
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:
$550
Tax: State & Local:
11.7
Two week minimum stay required, house can be rented Sat 8/8 to 8/22 or 8/9 to 8/23
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 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$8,000
7
8
9
10
11
12
13
$8,000
14
15
16
17
18
19
20
$8,000
21
22
23
24
25
26
27
$9,000
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
$12,500
12
13
14
15
16
17
18
$12,500
19
20
21
22
23
24
25
$12,500
26
27
28
29
30
31
$12,500
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$12,500
2
3
4
5
6
7
8
$14,000
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$14,000
23
24
25
26
27
28
29
$14,000
30
31
$12,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$12,500
6
7
8
9
10
11
12
$8,000
13
14
15
16
17
18
19
$7,000
20
21
22
23
24
25
26
$7,000
27
28
29
30
$7,000
Clean Fee:
$550 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
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
Stylish New Home, In Village Location, Patio Area with Outdoor Living and Dining, Walk to town!
This beautiful four-bedroom home boasts an open-concept living space, including a large kitchen and dining area, as well as a sitting area with a wet bar, beverage cooler and large...Read more
Quintessental 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:
$10,000 - $14,000
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$12,000
7
8
9
10
11
12
13
$12,000
14
15
16
17
18
19
20
$12,000
21
22
23
24
25
26
27
$12,000
28
29
30
$14,000
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$14,000
5
6
7
8
9
10
11
$14,000
12
13
14
15
16
17
18
$14,000
19
20
21
22
23
24
25
$14,000
26
27
28
29
30
31
$14,000
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$14,000
2
3
4
5
6
7
8
$14,000
9
10
11
12
13
14
15
$14,000
16
17
18
19
20
21
22
$14,000
23
24
25
26
27
28
29
$14,000
30
31
$14,000
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$14,000
6
7
8
9
10
11
12
$12,000
13
14
15
16
17
18
19
$12,000
20
21
22
23
24
25
26
$12,000
27
28
29
30
$10,000
Clean Fee:
$450
Tax: State & Local:
11.7
Owner will rent off weekend arrival and departure dates. Please inquire!
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
Please note: This beautiful new home is in the process of being furnished into April. The photos provided are a sampling of the decor. All furnishings and household items will...Read more
Location:
Oak Bluffs
Sleeps:
8
Bedrooms:
3
Baths:
3
Price Range:
$5,230 - $13,960
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$9,760
7
8
9
10
11
12
13
$9,760
14
15
16
17
18
19
20
$9,760
21
22
23
24
25
26
27
$9,760
28
29
30
$9,760
July 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
$9,760
5
6
7
8
9
10
11
$10,460
12
13
14
15
16
17
18
$10,460
19
20
21
22
23
24
25
$10,460
26
27
28
29
30
31
$10,460
August 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
$10,460
2
3
4
5
6
7
8
$13,960
9
10
11
12
13
14
15
$13,960
16
17
18
19
20
21
22
$13,960
23
24
25
26
27
28
29
$13,960
30
31
$9,060
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$9,060
6
7
8
9
10
11
12
$6,650
13
14
15
16
17
18
19
$6,650
20
21
22
23
24
25
26
$6,650
27
28
29
30
$6,650
Clean Fee:
$600 per week
Tax: State & Local:
11.7
3 night minimum stay required, May, June, September, October, 4 night minimum July to 7/19
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
Perfect in Town Location. Just 1 to 2 blocks to Beach, Town Center & Harbor Area, Walk to and from the Ferry
Centrally located in the heart of Oak Bluffs, walk 1-2 blocks to the beach, public tennis courts, and town & harbor areas. This wonderful large home has a large wrap-around porch for relaxing, 7...Read more
Spacious Colonial with Contemporary Detailing in Fresh Pond Estates, Mulitpe 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:
$4,900 - $13,500
June 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
6
$5,500
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
$5,500
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
$6,500
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
$13,500
9
10
11
12
13
14
15
$13,500
16
17
18
19
20
21
22
$15,000
23
24
25
26
27
28
29
$7,900
30
31
$6,500
September 2026
Su
Mo
Tu
We
Th
Fr
Sa
Week
1
2
3
4
5
$6,500
6
7
8
9
10
11
12
$5,500
13
14
15
16
17
18
19
$5,100
20
21
22
23
24
25
26
$5,100
27
28
29
30
$5,100
Clean Fee:
$500 per week ($375 for interim cleaning on multiple week rentals)
Herring Creek Summer Retreat, Waterfront, Oversized Pool, Private Association Shore Beach
Nestled into an expansive waterfront lot on the Edgartown Great Pond in prestigious Herring Creek Farm, you’ll find this true Vineyard casual cottage adorned with antique Vineyard collections of original...Read more
