Vacation Rentals

Depart OnlyArrive OnlyBookedAvailable

Displaying 91 - 100 of 333

Add Favorite
 
<< >>
View Larger Images (31 images)
Get My Quote
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. 

This three-bedroom home...Read more

Location: 
West Tisbury
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSa
 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
SuMoTuWeThFrSa
 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 2026
SuMoTuWeThFrSa
 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 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
$1,750
13
14
15
16
17
18
19
$1,750
20
21
22
23
24
25
26
$1,750
27
28
29
30
 $1,750
Clean Fee: 
$405 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (19 images)
Get My Quote

DRAPG

(0)Inquire/Share
Property Details
Mink Meadow Guest Cottage, Overlooks Golf Course, Walk to Beach 5 min walk from House, Mink Meadows Golf Course, 1 mile to Clubhouse

Cozy guest cottage with designer touches throughout. As the guest cottage to the main house, this adorable cottage is private from the main house and has its own drive and...Read more

Location: 
Vineyard Haven
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,900 - $1,900
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,900
7
8
9
10
11
12
13
$1,900
14
15
16
17
18
19
20
$1,900
21
22
23
24
25
26
27
$1,900
28
29
30
 $2,100
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$2,100
5
6
7
8
9
10
11
$2,100
12
13
14
15
16
17
18
$2,100
19
20
21
22
23
24
25
$2,100
26
27
28
29
30
31
 $2,100
August 2026
SuMoTuWeThFrSaWeek
 1
$2,100
2
3
4
5
6
7
8
$2,100
9
10
11
12
13
14
15
$2,100
16
17
18
19
20
21
22
$2,100
23
24
25
26
27
28
29
$2,100
30
31
 $1,900
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,900
6
7
8
9
10
11
12
$1,900
13
14
15
16
17
18
19
$1,900
20
21
22
23
24
25
26
$1,900
27
28
29
30
 $1,900
Clean Fee: 
$150 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (41 images)
Get My Quote

DRAPM

(0)Inquire/Share
Property Details
Mink Meadows Family Compound, Private Heated Pool, Walk or Drive to Private Association Beach, Beautifully Landscaped Yard, Deck and Patio, Golf 1 Mile from House

Spacious 4 Bedroom, 3.5 bath family compound with 28 x 14  heated pool, multiple indoor/outdoor living spaces situated in Mink Meadows Association. 

Mink Meadows Public Golf Course is just a short drive...Read more

Location: 
Vineyard Haven
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,400 - $8,500
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$4,400
7
8
9
10
11
12
13
$4,400
14
15
16
17
18
19
20
$6,500
21
22
23
24
25
26
27
$6,500
28
29
30
 $7,800
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,800
5
6
7
8
9
10
11
$7,800
12
13
14
15
16
17
18
$7,800
19
20
21
22
23
24
25
$7,800
26
27
28
29
30
31
 $8,500
August 2026
SuMoTuWeThFrSaWeek
 1
$8,500
2
3
4
5
6
7
8
$8,500
9
10
11
12
13
14
15
$8,500
16
17
18
19
20
21
22
$8,500
23
24
25
26
27
28
29
$8,500
30
31
 $6,500
September 2026
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
$6,500
27
28
29
30
 $6,500
Clean Fee: 
$550 per week
Tax: State & Local: 
11.7

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

 

Pool heated to 81 degrees June & September additional $250 per week. Requests for higher temperature, please contact your agent for details. 

 

Pool heated to 81 degrees May & October additional $350 per week. Requests for higher temperature, please contact your agent for details.

 

Add Favorite
 
<< >>
View Larger Images (27 images)
Get My Quote

DUREJ

(0)Inquire/Share
Property Details

This luxuriously updated tri-level condo retreat at Quail Run in the community of homes known as Sengekontacket, has been transformed, bringing a fresh, coastal feel to every corner. The end...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
2
Baths: 
1
Price Range:
$70 - $5,000
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$3,500
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
$4,000
28
29
30
 $5,500
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$5,500
5
6
7
8
9
10
11
$5,000
12
13
14
15
16
17
18
$5,000
19
20
21
22
23
24
25
$5,000
26
27
28
29
30
31
 $5,500
August 2026
SuMoTuWeThFrSaWeek
 1
$5,500
2
3
4
5
6
7
8
$6,000
9
10
11
12
13
14
15
$6,000
16
17
18
19
20
21
22
$5,750
23
24
25
26
27
28
29
$5,000
30
31
 $4,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$4,000
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: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (46 images)
Get My Quote

ELLIK

(0)Inquire/Share
Property Details
Quintessential West Chop Waterfront Home. Private Beach, Spectacular Views

Enjoy the essence of summer at this waterfront home with a private beach just 50 yards in front of the house. Evenings enjoy the magnificent sunsets while relaxing on the...Read more

Location: 
Vineyard Haven
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
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
$25,000
28
29
30
 $28,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$28,000
5
6
7
8
9
10
11
$25,000
12
13
14
15
16
17
18
$25,000
19
20
21
22
23
24
25
$25,000
26
27
28
29
30
31
 $28,000
August 2026
SuMoTuWeThFrSaWeek
 1
$28,000
2
3
4
5
6
7
8
$28,000
9
10
11
12
13
14
15
$28,000
16
17
18
19
20
21
22
$28,000
23
24
25
26
27
28
29
$28,000
30
31
 $25,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$25,000
6
7
8
9
10
11
12
$17,500
13
14
15
16
17
18
19
$17,500
20
21
22
23
24
25
26
$17,500
27
28
29
30
 $17,500
Clean Fee: 
$800 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (24 images)
Get My Quote

ELOUA

(0)Inquire/Share
Property Details
Lovely updated Home , Village Area Edgartown, 7 minute Walk to Main St. Bike Paths at end of Street.

Minutes from downtown Edgartown's shops & restaurants, this cape style home features open concept living, air conditioning, a mini-split in the main living area, window units in all but 1st level...Read more

Location: 
Edgartown
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,650 - $7,350
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$6,650
7
8
9
10
11
12
13
$6,650
14
15
16
17
18
19
20
$6,650
21
22
23
24
25
26
27
$6,650
28
29
30
 $7,350
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,350
5
6
7
8
9
10
11
$7,350
12
13
14
15
16
17
18
$7,350
19
20
21
22
23
24
25
$7,350
26
27
28
29
30
31
 $7,350
August 2026
SuMoTuWeThFrSaWeek
 1
$7,350
2
3
4
5
6
7
8
$8,050
9
10
11
12
13
14
15
$8,050
16
17
18
19
20
21
22
$8,050
23
24
25
26
27
28
29
$8,050
30
31
 $6,650
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$6,650
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: 
$275 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (54 images)
Get My Quote

ENGLJ

(0)Inquire/Share
Property Details
Exquisite Estate Vacation Retreat, Main & Guest House, Affinity Pool, South Shore Waterviews, Sleeps 12 in 6 Bedrooms, Multiple Living & Entertaining Areas both indoors & out

Outstanding Chilmark Estate tucked on 9.5 private acres with sweeping views of the Atlantic Ocean and Chilmark Pond. This unique contemporary home features a heated infinity pool, screened porch, and expansive deck with...Read more

Location: 
Chilmark
Sleeps: 
12
Bedrooms: 
6
Baths: 
5
Price Range:
$0 - $0
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$35,000
7
8
9
10
11
12
13
$35,000
14
15
16
17
18
19
20
$35,000
21
22
23
24
25
26
27
$40,000
28
29
30
 $55,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$55,000
5
6
7
8
9
10
11
$50,000
12
13
14
15
16
17
18
$50,000
19
20
21
22
23
24
25
$50,000
26
27
28
29
30
31
 $60,000
August 2026
SuMoTuWeThFrSaWeek
 1
$60,000
2
3
4
5
6
7
8
$60,000
9
10
11
12
13
14
15
$60,000
16
17
18
19
20
21
22
$60,000
23
24
25
26
27
28
29
$50,000
30
31
 $30,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$30,000
6
7
8
9
10
11
12
$30,000
13
14
15
16
17
18
19
$30,000
20
21
22
23
24
25
26
$30,000
27
28
29
30
 
Clean Fee: 
$2000 per week
Tax: State & Local: 
11.7

Pool heated to 82 degrees in July and August included in rental rate

Pool heated to 82 degrees June & September additional surcharge $350 per week

Pool heated to 82 degrees May & October additional surcharge $450 per week

Add Favorite
 
<< >>
View Larger Images (44 images)
Get My Quote

EW138

(0)Inquire/Share
Property Details
Beautiful Oak Bluffs Home, 20 x 40 Heated Pool, 6 Bedrooms, 4 baths, Sleeps 14, Screened Porch, Multiple Living Spaces

Oak Bluffs vacation retreat with multiple indoor, and outdoor living and entertaining areas. The highlight of this spacious summer home is the heated Gunite pool with waterfall, bluestone patio, and...Read more

Location: 
Oak Bluffs
Sleeps: 
14
Bedrooms: 
6
Baths: 
4
Price Range:
$70 - $12,000
June 2026
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
 $18,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$18,000
5
6
7
8
9
10
11
$18,900
12
13
14
15
16
17
18
$19,000
19
20
21
22
23
24
25
$20,000
26
27
28
29
30
31
 $20,000
August 2026
SuMoTuWeThFrSaWeek
 1
$20,000
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
$16,900
30
31
 $12,000
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$12,000
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
 $12,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7

Pool Heated to 82 included in rental rate July and August, Spa in pool is heated to same the temperature as pool.

 

Additional Spa Heat 6 to 10pm, $250 per week. Available upon request. 

 

Pool Heated to 82 June & Sept additional $275 per week. May & October additional $350 per week. 

 

Firepit seen in photos is not for renter use. 

Add Favorite
fennb13-01-exterior.jpg
 
<< >>
View Larger Images (13 images)
Get My Quote

FENNB

(0)Inquire/Share
Property Details
Menemsha, Water View, Walk to beach
Location: 
Chilmark
Sleeps: 
4
Bedrooms: 
2
Baths: 
1
Price Range:
$1,950 - $3,200
June 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
$1,950
7
8
9
10
11
12
13
$1,950
14
15
16
17
18
19
20
$1,950
21
22
23
24
25
26
27
$1,950
28
29
30
 $3,000
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$3,000
5
6
7
8
9
10
11
$3,000
12
13
14
15
16
17
18
$3,000
19
20
21
22
23
24
25
$3,000
26
27
28
29
30
31
 $3,200
August 2026
SuMoTuWeThFrSaWeek
 1
$3,200
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
 $1,950
September 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
$1,950
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: 
$200 per week
Tax: State & Local: 
11.7
Add Favorite
 
<< >>
View Larger Images (22 images)
Get My Quote

FERGN

(0)Inquire/Share
Property Details
5 minute walk to town center.

Enjoy a view of Vineyard Haven harbor from this 1898 Captain's home. Walk to town, tennis, dining, library, etc... The Captain Henry Stevenson house has been renovated to include a...Read more

Location: 
Vineyard Haven
Sleeps: 
9
Bedrooms: 
5
Baths: 
2
Price Range:
$7,400 - $7,400
June 2026
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
 $7,400
July 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
$7,400
5
6
7
8
9
10
11
$7,400
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
August 2026
SuMoTuWeThFrSaWeek
 1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
$6,900
23
24
25
26
27
28
29
$6,900
30
31
 
September 2026
SuMoTuWeThFrSa
 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: 
$350 per week
Tax: State & Local: 
11.7

Pages