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Originally a fishing village and a bustling seaport during the whaling era, the Vineyard Haven of today is home to charming shops, popular restaurants and a beautiful harbor, often filled with private yachts.

47 Vacation Properties in Vineyard Haven

Vineyard Haven vacation rentals that sleep 16

Tisbury
ID 35301
6 BR
4 baths
Sleeps 16
Beautiful, Spacious Home Sleeps 16
Beautiful, Spacious Home Sleeps 16
Distance to beach: 8/10 mi to East Chop Beach Tisbury Tisbury Town Beach
Summer:
$1,000 - $1,200/night
$5,000 - $8,400/wk
Off Season:
$1,000 - $1,350/night
$4,000 - $7,000/wk

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven
ID 27594
5 BR
2 ½ baths
Sleeps 14
Main House near Lagoon & Town
Main House near Lagoon & Town
Distance to beach: 4 miles State Beach and Less than one mile to Lagoon Beach via wooded hike
Summer:
$6,500/wk
Off Season:
$500 - $900/night
$3,750 - $5,000/wk

Vineyard Haven vacation rentals that sleep 12

Vineyard Haven
ID 18585
7 BR
3 ½ baths
Sleeps 12
324 Main Street
324 Main Street
Distance to beach: 250 yards to Tisbury Town Beach off Owen Little Wa
1 review read review
Summer:
$4,000 - $5,500/wk
Off Season:
$4,000/wk
Vineyard Haven
ID 35726
6 BR
6 ½ baths
Sleeps 12
Historic Private Estate with Pool and Tennis
Historic Private Estate with Pool and Tennis
Distance to beach: 2.4 mi to Lake Tashmoo Town Beach
Summer:
$22,000 - $25,000/wk
$100,000/mo
Off Season:
$22,000/wk
$88,000/mo
Tisbury
ID 35577
5 BR
4 ½ baths
Sleeps 12
Reunion House, Car, Ferry Res.
Reunion House, Car, Ferry Res.
Distance to beach: 2.2 mi to Lambert's Cove Beach
Summer:
$6,500 - $12,000/wk
$29,000 - $38,000/mo
Off Season:
$4,000 - $9,000/wk
$14,000 - $28,000/mo

Vineyard Haven vacation rentals that sleep 11

Vineyard Haven
ID 34385
Summer:
$11,500 - $17,500/wk
Off Season:
$800 - $10,500/wk
$18,850 - $29,500/mo
3

Vineyard Haven vacation rentals that sleep 10

Vineyard Haven
ID 16690
5 BR
2 ½ baths
Sleeps 10
Vineyard Haven (in town), Recently Renovated, Harbor views
Vineyard Haven (in town), Recently Renovated, Harbor views
Distance to beach: 1 block to Owen Park Beach
11 reviews read reviews
OWNER SPECIAL:
One week starting August 27 still available. Can extend thru Labor Day weekend, if interested.
Summer:
$6,700/wk
3
Vineyard Haven
ID 30881
Summer:
$9,500 - $10,000/wk
Off Season:
$9,000/wk
Lower Makonikey, off Lambert's
ID 3695
4 BR
3 baths
Sleeps 10
Secluded 4+br home: short walk to private association beach
Secluded 4+br home: short walk to private association beach
Distance to beach: 4/10 mile to private Lower Makonikey Beach
16 reviews read reviews
Summer:
$3,800 - $4,400/wk
Off Season:
$550 - $575/night
$3,500 - $38,000/wk
5
Vineyard Haven
ID 35271
Summer:
$7,000 - $12,000/wk
Off Season:
$5,000 - $8,000/wk
2
Vineyard Haven
ID 34602
3 BR
3 baths
Sleeps 10
Tranquil Modern Victorian near Private Association Beach
Tranquil Modern Victorian near Private Association Beach
Distance to beach: 2.4 mi to Lambert's Cove Beach
1 review read review
Summer:
$4,000 - $5,100/wk
$17,000 - $18,400/mo
Off Season:
$450 - $650/night
$3,000 - $3,800/wk
$11,400 - $12,500/mo
4

Vineyard Haven vacation rentals that sleep 9

Vineyard Haven
ID 27377
Summer:
$12,000 - $18,500/wk
Off Season:
$10,000 - $12,000/wk
Vineyard Haven
ID 35172
Summer:
$3,200 - $8,000/wk
Off Season:
$3,000 - $4,000/wk
Vineyard Haven
ID 18566
4 BR
2 baths
Sleeps 9
Waterfront Cottage with Private Beach
Waterfront Cottage with Private Beach
Distance to beach: On the beach
3 reviews read reviews
Summer:
$4,200 - $5,300/wk
Off Season:
$1,450 - $3,200/wk
Vineyard Haven
ID 29874
4 BR
4 baths
Sleeps 9
New Construction 4BR/4BA Central A/C In-Town Vineyard Haven
New Construction 4BR/4BA Central A/C In-Town Vineyard Haven
Distance to beach: .5 miles Owen Park Beach and Owen Park Beach 1/2 mile
Summer:
$9,000 - $18,000/wk
Off Season:
$800/night
$6,000 - $10,000/wk
2

Vineyard Haven vacation rentals that sleep 8

Vineyard Haven
ID 30205
4 BR
2 ½ baths
Sleeps 8
Shelbourne House, walking distance to Vineyard Haven town.
Shelbourne House, walking distance to Vineyard Haven town.
Distance to beach: Owen Park Beach, 3/4 mile Owen Park Beach and Eastville Point Beach 1.5 mi.
5 reviews read reviews
Summer:
$6,000 - $12,000/wk
Off Season:
$6,000 - $8,000/wk
Vineyard Haven
ID 34561
4 BR
2 baths
Sleeps 8
A/C Home w/ Peaceful Pool
A/C Home w/ Peaceful Pool
Distance to beach: 10 minute walk to Owen's Beach State Park
1 review read review
Summer:
$5,500 - $9,000/wk
Off Season:
$5,500 - $6,000/wk
Vineyard Haven
ID 28424
4 BR
4 ½ baths
Sleeps 8
Captain Spring House: In-town Luxury with Water Views
Captain Spring House: In-town Luxury with Water Views
Distance to beach: 3/10 mile Owen Park Bch, 1/2 mile Town Beach
Summer:
$7,990 - $9,990/wk
Off Season:
$1,000/night
$5,990 - $8,990/wk
4
Vineyard Haven
ID 36005
4 BR
2 baths
Sleeps 8
Contemporary Home with a Heated Pool
Contemporary Home with a Heated Pool
Distance to beach: 0.9 mi to Owen Park Beach and 1.7 mi to Lake Tashmoo Town Beach
OWNER SPECIAL:
THE MONTH OF JULY 2022 IS WIDE OPEN! BOOK BEFORE WEEKS ARE GONE!
Summer:
$4,500 - $8,000/wk
Off Season:
$4,000 - $6,500/wk
Vineyard Haven
ID 28634
4 BR
2 baths
Sleeps 8
Secluded In-Town Wonder: The Best Of Both Worlds
Secluded In-Town Wonder: The Best Of Both Worlds
Distance to beach: 1/2 mile to Owen Park Beach and 1/4 mile to Owen Park Beach.
Summer:
$4,100 - $4,950/wk
Off Season:
$550 - $600/night
$3,450 - $3,850/wk
Vineyard Haven
ID 3110
3 BR
2 baths
Sleeps 8
Peaceful Escape | Charming Vacation Home w/ AC
Peaceful Escape | Charming Vacation Home w/ AC
Distance to beach: 1.0 mile Owen Park Beach and 1.5 miles Lake Tashmoo Town Beach
10 reviews read reviews
Summer:
$2,800 - $3,500/wk
Off Season:
$400/night
$2,200 - $2,800/wk
Vineyard Haven
ID 29178
Summer:
$8,500 - $9,800/wk
Off Season:
$6,500 - $9,800/wk
Vineyard Haven
ID 36073
3 BR
3 baths
Sleeps 8
West Chop/Private Setting...Access to Two Private Beaches
West Chop/Private Setting...Access to Two Private Beaches
Distance to beach: 1/4 mile to Private Association Beach
Summer:
$5,600/wk
Off Season:
$500 - $700/night
$4,900 - $5,600/wk
2

Vineyard Haven vacation rentals that sleep 7

Vineyard Haven
ID 29593
4 BR
2 ½ baths
Sleeps 7
Central Air - Family friendly - Walk to Town & Beach
Central Air - Family friendly - Walk to Town & Beach
Distance to beach: 2/10 mile Tisbury Town Beach and 3/10 Owen Park Beach
10 reviews read reviews
Summer:
$3,500 - $4,900/wk
Off Season:
$300/night
$2,100 - $3,500/wk
5
Vineyard Haven
ID 35457
3 BR
1 bath
Sleeps 7
Family Home Close to Downtown
Family Home Close to Downtown
Distance to beach: 1/2 mi to Owen Park Beach
Summer:
$3,500 - $4,500/wk
3

Vineyard Haven vacation rentals that sleep 6

West Chop
ID 23406
Off Season:
$3,500 - $4,000/wk
Vineyard Haven
ID 11693
3 BR
2 baths
Sleeps 6
Charming Cottage near West Chop- Vineyard Haven
Charming Cottage near West Chop- Vineyard Haven
Distance to beach: 2 Blks to Owen Little Beach-1 mi. to Tashmoo Beach
5 reviews read reviews
Summer:
$3,150/wk
Off Season:
$2,500 - $3,150/wk
Vineyard Haven
ID 15230
Summer:
$2,300 - $2,500/wk
Off Season:
$1,800 - $2,000/wk
4
Vineyard Haven
ID 29492
3 BR
2 baths
Sleeps 6
Amazing Views Year-Round, Private Beach, Great for Kayaking
Amazing Views Year-Round, Private Beach, Great for Kayaking
Distance to beach: Private beach on the property, 3/10 mile to public
21 reviews read reviews
Summer:
$4,650 - $5,650/wk
Off Season:
$369 - $599/night
$2,975 - $4,650/wk
5
Vineyard Haven
ID 30546
3 BR
2 baths
Sleeps 6
Completely Renovated 3-Bedroom Vineyard Haven Duplex
Completely Renovated 3-Bedroom Vineyard Haven Duplex
Distance to beach: 1.2 miles to Owen Park Beach
15 reviews read reviews
OWNER SPECIAL:
Cancellation alert for prime summer week! Aug 20 - 27.
Summer:
$4,500 - $5,000/wk
Off Season:
$500 - $642/night
$3,000 - $4,500/wk
2
Vineyard Haven
ID 33283
3 BR
1 ½ bath
Sleeps 6
Commanding Lagoon Waterfront, Private Beach: 180° View
Commanding Lagoon Waterfront, Private Beach: 180° View
Distance to beach: 20 ft from the your own 250' private Lagoon Beach!
6 reviews read reviews
OWNER SPECIAL:
Last Minute Rental: TAKE 25% OFF! (Start Date within 2 weeks!) Tax Exempt When Renting 32+ Nights!
Summer:
$8,000 - $11,500/wk
Off Season:
$5,250 - $8,750/wk
Vineyard Haven
ID 34233
3 BR
1 ½ bath
Sleeps 6
Historic, Renovated, In Town Cape
Historic, Renovated, In Town Cape
Distance to beach: 1.0 mi to Tisbury Town Beach
4 reviews read reviews
Summer:
$3,500 - $5,000/wk
Off Season:
$250 - $650/night
$1,750 - $3,850/wk
4
VIneyard Haven
ID 35855
3 BR
2 ½ baths
Sleeps 6
Skiff
Skiff
Distance to beach: 1.3 mi to Tisbury Town Beach and 300 yards to Harbor
Summer:
$6,800 - $10,500/wk
Off Season:
$6,800 - $7,000/wk
4
Vineyard Haven
ID 19399
3 BR
2 baths
Sleeps 6
Charming Bright Sunny Cape Home in Vineyard Haven
Charming Bright Sunny Cape Home in Vineyard Haven
Distance to beach: 10 minute walk to Owens Beach
9 reviews read reviews
Summer:
$1,800 - $2,300/wk
Off Season:
$250/night
$1,100 - $2,100/wk
$1,400 - $1,600/mo
2
Vineyard Haven
ID 4482
2 BR
1 bath
Sleeps 6
Hine's Point Waterfront
Hine's Point Waterfront
Distance to beach: 1/2 mile
1 review read review
Summer:
$3,600 - $3,800/wk
Off Season:
$2,600 - $3,500/wk
Vineyard Haven
ID 16365
2 BR
3 baths
Sleeps 6
Tashmoo Wood Condo
Tashmoo Wood Condo
Distance to beach: 1.5 mi to Lake Tashmoo Town Beach (Herring Creek)
Summer:
$2,600 - $3,000/wk
Off Season:
$2,000 - $3,000/wk
$8,000 - $12,000/mo

Vineyard Haven vacation rentals that sleep 5

Vineyard Haven
ID 7366
Summer:
$2,950/wk
Off Season:
$2,212 - $2,950/wk
Vineyard Haven
ID 29565
2 BR
2 baths
Sleeps 5
Vineyard Charmer
Vineyard Charmer
Distance to beach: 1 mile Owen Park Beach
Summer:
$2,650 - $3,000/wk
Off Season:
$1,800 - $2,600/wk
2

Vineyard Haven vacation rentals that sleep 4

Vineyard Haven
ID 7436
2 BR
1 bath
Sleeps 4
Relax..You're on Island Time...A little piece of paradise..
Relax..You're on Island Time...A little piece of paradise..
Distance to beach: 1/2 mile Tisbury Town Beach and 1/2 mile Owen Park Beach
39 reviews read reviews
Summer:
$1,800 - $1,900/wk
Off Season:
$200 - $250/night
$1,500 - $1,900/wk
$1,500/mo
Vineyard Haven
ID 13842
2 BR
1 ½ bath
Sleeps 4
Beachfront paradise on beautiful Martha's Vineyard
Beachfront paradise on beautiful Martha's Vineyard
Distance to beach: Beachfront on Lake Tashmoo
Summer:
$3,350/wk
Off Season:
$2,250 - $3,350/wk
Vineyard Haven
ID 16502
2 BR
1 bath
Sleeps 4
Fabulous Contemporary With Steinway Piano & Tremendous Charm
Fabulous Contemporary With Steinway Piano & Tremendous Charm
Distance to beach: 3/4 Mile Owen Park Beach and Owen Park Beach, Appx. 3/4 mile from house.
OWNER SPECIAL:
Tax Exempt When Renting 32+ Nights!
Summer:
$3,050 - $3,850/wk
Off Season:
$500 - $550/night
$1,700 - $2,950/wk
4
Vineyard Haven
ID 31287
Summer:
$1,900/wk
Off Season:
$1,000 - $2,000/wk
$1,800/mo
2
Vineyard Haven
ID 34386
2 BR
2 baths
Sleeps 4
Architect Designed Two Bedroom Refuge w/Shared Private Beach
Architect Designed Two Bedroom Refuge w/Shared Private Beach
Distance to beach: Wonderful shared private beach just 200 feet away!
Summer:
$3,800 - $4,700/wk
Off Season:
$2,200 - $3,600/wk
4
West Chop
ID 35609
2 BR
1 bath
Sleeps 4
Cozy West Chop Hideaway- New Renovation
Cozy West Chop Hideaway- New Renovation
Distance to beach: 4/10 mi to Tiny Grove Street Beach
Summer:
$2,800 - $3,200/wk
Off Season:
$1,600 - $2,800/wk
4
Vineyard Haven
ID 21680
1 BR
1 bath
Sleeps 4
CCC - Cute, Cozy Condo with Pool
CCC - Cute, Cozy Condo with Pool
Distance to beach: Owen Park Beach under 1/2 mile
5 reviews read reviews
Summer:
$1,050/wk
Off Season:
$950/wk

Vineyard Haven vacation rentals that sleep 2

Vineyard Haven
ID 35975
1 BR
1 bath
Sleeps 2
Quaint Vineyard Haven One Bedroom Guest House
Quaint Vineyard Haven One Bedroom Guest House
Distance to beach: 1.0 Owen Park Beach and Eastville Beach, Oak Bluffs 3 miles away
OWNER SPECIAL:
Available to rent for the season or a monthly basis.
Summer:
$8,000/mo
Vineyard Haven
ID 7718
1 BR
1 bath
Sleeps 2
Waterview of Vineyard Sound, sleeps 2.
Waterview of Vineyard Sound, sleeps 2.
Distance to beach: 10 minute walk to Owen Little Way Beach.
3 reviews read reviews
Summer:
$1,500/wk
Off Season:
$1,300/wk