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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.

50 Vacation Properties in Vineyard Haven
Sleeps

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven
ID 27594
5 BR
2 ½ baths
Sleeps 14
Main House near Lagoon & Town (SLEEPS 14)
Main House near Lagoon & Town (SLEEPS 14)
Distance to beach: 2 Miles to Eastville Beach
Summer:
$5,000 - $6,000/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 Owen Little Beach
1 review read review
Summer:
$3,000 - $4,000/wk
Off Season:
$3,000/wk
Vineyard Haven
ID 30881
Summer:
$6,800/wk
Off Season:
$6,800/wk

Vineyard Haven vacation rentals that sleep 10

Vineyard Haven
ID 29492
6 BR
2 baths
Sleeps 10
Family-Friendly Lakefront, Private Beach, Amazing Views
Family-Friendly Lakefront, Private Beach, Amazing Views
Distance to beach: 50 yds. to private bch, 3/10 mile to White's Beach
Summer:
$3,675 - $5,845/wk
Off Season:
$420 - $675/night
$2,065 - $3,675/wk
Vineyard Haven
ID 16690
Summer:
$5,200 - $5,600/wk
Off Season:
$3,200 - $4,200/wk
Vineyard Haven
ID 22635
5 BR
4 ½ baths
Sleeps 10
Vineyard Haven Golf and Beach Retreat
Vineyard Haven Golf and Beach Retreat
Distance to beach: .8 miles to Mink Meadows Association Beach
3 reviews read reviews
Summer:
$5,500 - $6,250/wk
Off Season:
$700 - $850/night
$3,000 - $5,000/wk
Vineyard Haven
ID 30024
5 BR
5 baths
Sleeps 10
The CAVU Mansion on Bellevue
The CAVU Mansion on Bellevue
Distance to beach: 1.6 miles to Owen Park Beach
11 reviews read reviews
Summer:
$525 - $1,116/night
$5,521 - $7,818/wk
Off Season:
$336 - $789/night
$2,521 - $5,065/wk
Oak Bluffs
ID 30891
5 BR
2 baths
Sleeps 10
Stunning Victorian Inkwell Beach
Stunning Victorian Inkwell Beach
Distance to beach: Inkwell beach - 100 steps
Off Season:
$600 - $800/night
$5,000/wk
Makonikey, off Lambert's Cove
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
9 reviews read reviews
Summer:
$3,800/wk
Off Season:
$500 - $525/night
$3,500 - $3,675/wk

Vineyard Haven vacation rentals that sleep 9

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
1 review read review
Summer:
$3,000 - $5,000/wk
Off Season:
$1,250 - $3,500/wk
Vineyard Haven
ID 29874
Summer:
$6,000 - $9,996/wk
Off Season:
$650/night
$4,550 - $6,500/wk
Vineyard Haven
ID 16951
4 BR
2 baths
Sleeps 9
10 min.walk beach or town; 4 BR 2B private
10 min.walk beach or town; 4 BR 2B private
Distance to beach: .4 to outer harbor beach; 1.3 to Lake Tashm
6 reviews read reviews

Vineyard Haven vacation rentals that sleep 8

Vineyard Haven
ID 27679
4 BR
4 ½ baths
Sleeps 8
Renovated Modern In Town Luxury Home
Renovated Modern In Town Luxury Home
Distance to beach: Owen Park Beach is 2 blocks from our home
3 reviews read reviews
Summer:
$5,500 - $8,990/wk
Off Season:
$785/night
$5,500/wk
Vineyard Haven
ID 27718
4 BR
3 baths
Sleeps 8
Cat Hollow: Four Bedroom Home with Views of the Harbor
Cat Hollow: Four Bedroom Home with Views of the Harbor
Distance to beach: .6 mile Owen Park, Vineyard Haven
Summer:
$4,000 - $5,800/wk
$5,000 - $5,800/mo
Off Season:
$4,000 - $5,500/wk
$4,000 - $5,500/mo
Vineyard Haven
ID 28257
4 BR
3 ½ baths
Sleeps 8
Picturesque walk to beach, Sleeps 8!
Picturesque walk to beach, Sleeps 8!
Distance to beach: Tashmoo Beach 1 Mile
Summer:
$4,800 - $6,000/wk
$5,000 - $6,000/mo
Off Season:
$4,800 - $5,000/wk
$4,800 - $5,500/mo
Vineyard Haven
ID 29569
4 BR
2 ½ baths
Sleeps 8
Perfect Vineyard Stay. Central a/c and 4 Bedrooms.
Perfect Vineyard Stay. Central a/c and 4 Bedrooms.
Distance to beach: Owen Park 1 mile Vineyard Haven Harbor
2 reviews read reviews
OWNER SPECIAL:
FERRY TICKETS FOR YOUR VEHICLE WILL BE AVAILABLE FOR JULY-AUGUST 2019 WEEKS.
Summer:
$2,775 - $2,975/wk
Off Season:
$2,675 - $2,775/wk
Vineyard Haven
ID 30205
4 BR
2 ½ baths
Sleeps 8
Shelbourne House, walking distance to town. Beautiful!
Shelbourne House, walking distance to town. Beautiful!
Distance to beach: Eastville Point Beach 1.6 mi.
2 reviews read reviews
Summer:
$4,500 - $6,000/wk
Off Season:
$400 - $600/night
$2,100 - $5,000/wk
Tisbury
ID 31045
4 BR
4 baths
Sleeps 8
Walk to Main Street & Beach - No car needed!
Walk to Main Street & Beach - No car needed!
Distance to beach: 1/4 mile to Owen Park Beach
Summer:
$5,000 - $8,000/wk
Off Season:
$400 - $715/night
$2,800 - $7,000/wk
Vineyard Haven
ID 31296
4 BR
3 ½ baths
Sleeps 8
Pilot Hill Farm Delight: Walk to Private Assn Beach
Pilot Hill Farm Delight: Walk to Private Assn Beach
Distance to beach: 1/3 mile to Pilot Hill Farm's North Shore beach
Summer:
$6,000 - $6,500/wk
Off Season:
$6,000/wk
Oak Bluffs
ID 31351
4 BR
1 ½ bath
Sleeps 8
Classic Vineyard Home in the Center of Oak Bluffs
Classic Vineyard Home in the Center of Oak Bluffs
Distance to beach: .5 mile to Inkwell Beach
Summer:
$2,800/wk
Off Season:
$2,800/wk
Vineyard Haven
ID 13591
4 BR
2 baths
Sleeps 8
Charming, New Remodel, Tree-Lined Lane 3 Blocks from Ferry
Charming, New Remodel, Tree-Lined Lane 3 Blocks from Ferry
Distance to beach: .3 mile to Owen Little Beach, .6 mile to Tashmoo
10 reviews read reviews
Off Season:
$150 - $350/night
$2,200 - $2,500/wk
$7,000/mo
Vineyard Haven
ID 3110
3 BR
2 baths
Sleeps 8
Charming Vacation Home w/ AC
Charming Vacation Home w/ AC
Distance to beach: 1 mile to Owen Pk Beach, 1.5 miles to Lake Tashmoo
4 reviews read reviews
OWNER SPECIAL:
Winter Season Special: December through February $1200 per week.
Summer:
$2,500/wk
Off Season:
$300/night
$1,500 - $2,500/wk
Vineyard Haven
ID 29178
Summer:
$3,500 - $6,500/wk
Off Season:
$350 - $400/night
$3,000 - $4,500/wk
Downtown Vineyard Haven
ID 29406
3 BR
3 ½ baths
Sleeps 8
New ''Modern Farmhouse'' - Walk to Town & Beach!
New ''Modern Farmhouse'' - Walk to Town & Beach!
Distance to beach: 10 minute walk to Owen Park Beach
2 reviews read reviews
Summer:
$4,500 - $7,925/wk
Off Season:
$3,995 - $7,425/wk
Vineyard Haven
ID 11449
3 BR
3 baths
Sleeps 8
Beautiful, spacious home with Private Beach, Pool and Tennis
Beautiful, spacious home with Private Beach, Pool and Tennis
Distance to beach: 1 mile to association private beach and dock
1 review read review
Off Season:
$2,000 - $2,800/wk

Vineyard Haven vacation rentals that sleep 6

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:
$2,000 - $2,300/wk
Off Season:
$2,000 - $2,300/wk
$1,200 - $1,400/mo
Vineyard Haven
ID 6517
3 BR
1 bath
Sleeps 6
Oceanfront & Lakefront Home/ Ferry tickets for July 28 week!
Oceanfront & Lakefront Home/ Ferry tickets for July 28 week!
Distance to beach: private ocean beach and private lakefront beach
Summer:
$5,000 - $6,000/wk
$30,000/mo
Off Season:
$4,000 - $6,000/wk
$8,000 - $25,000/mo
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
8 reviews read reviews
Summer:
$1,800 - $2,200/wk
Off Season:
$1,000 - $2,100/wk
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
3 reviews read reviews
Summer:
$2,500 - $3,000/wk
$10,000 - $12,000/mo
Off Season:
$285 - $425/night
$1,200 - $3,000/wk
$2,000 - $4,000/mo
Vineyard Haven
ID 30849
3 BR
2 ½ baths
Sleeps 6
Newly Renovated Quiet Retreat with Central AC!
Newly Renovated Quiet Retreat with Central AC!
Distance to beach: 1/2 mile to Lagoon Pond
Summer:
$2,500 - $3,600/wk
$12,800 - $16,100/mo
Off Season:
$250 - $290/night
$2,000 - $2,500/wk
$7,500 - $12,800/mo
Vineyard Haven
ID 15230
Off Season:
$250 - $300/night
$1,000 - $1,500/wk
Vineyard Haven
ID 25299
3 BR
2 baths
Sleeps 6
Charming 3 bedroom Cape in Vineyard Haven
Charming 3 bedroom Cape in Vineyard Haven
Distance to beach: Owen Pk / Lk Tashmoo-1 mi & Trustees Properties
4 reviews read reviews
Off Season:
$2,000 - $2,200/wk
Vineyard Haven
ID 24927
3 BR
2 baths
Sleeps 6
Private, charming in-town VH home, walk to ferry & beach
Private, charming in-town VH home, walk to ferry & beach
Distance to beach: Owen Park town beach under 1/2 mile
11 reviews read reviews
Off Season:
$1,800/mo
Vineyard Haven
ID 30017
3 BR
3 baths
Sleeps 6
Nature's Pocket
Nature's Pocket
Distance to beach: 1.6 Miles to Owen Park Beach
12 reviews read reviews
Summer:
$533 - $1,007/night
$2,826 - $6,891/wk
Off Season:
$197 - $663/night
$1,372 - $2,860/wk
Vineyard Haven
ID 30347
3 BR
2 ½ baths
Sleeps 6
Treehouse: Vineyard Haven Gem: close to all, & Private
Treehouse: Vineyard Haven Gem: close to all, & Private
Distance to beach: less than a mile to Owen Park Beach
5 reviews read reviews
Summer:
$3,000 - $3,300/wk
$12,000/mo
Off Season:
$350/night
$2,500 - $3,000/wk
$8,000 - $10,000/mo
Vineyard Haven
ID 16365
2 BR
3 baths
Sleeps 6
Tashmoo Woods Condo
Tashmoo Woods Condo
Distance to beach: 1.5 mi to Lake Tashmoo Town Beach (Herring Creek)
Summer:
$2,200 - $2,800/wk
Off Season:
$1,500 - $2,800/wk
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:
$3,000 - $3,500/wk
Off Season:
$2,100 - $3,300/wk
Vineyard Haven
ID 24589
2 BR
1 bath
Sleeps 6
The Lodge: Historic Cottage Overlooking Lake Tashmoo
The Lodge: Historic Cottage Overlooking Lake Tashmoo
Distance to beach: in front, then public Wilfrid's Pond .25 mile
2 reviews read reviews
Off Season:
$300 - $328/night
$2,100/wk
Vineyard Haven
ID 30015
2 BR
1 bath
Sleeps 6
The Vacation House
The Vacation House
Distance to beach: 9/10 mile to Owen Park Beach
12 reviews read reviews
Summer:
$231 - $406/night
$1,617 - $2,783/wk
Off Season:
$156 - $305/night
$924 - $1,513/wk

Vineyard Haven vacation rentals that sleep 5

Vineyard Haven
ID 7366
3 BR
1 ½ bath
Sleeps 5
Charming Lagoon Pond Cottage with Water View & Private Beach
Charming Lagoon Pond Cottage with Water View & Private Beach
Distance to beach: 3 miles to State Beach; private beach on property
11 reviews read reviews
Summer:
$2,600/wk
Off Season:
$1,950 - $2,600/wk
Vineyard Haven
ID 7436
2 BR
1 bath
Sleeps 5
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 to Owen Park beach on Harbor
35 reviews read reviews
Summer:
$1,600 - $1,800/wk
Off Season:
$250/night
$1,200 - $1,600/wk
$1,200 - $2,000/mo
Vineyard Haven
ID 29565
2 BR
2 baths
Sleeps 5
Vineyard Charmer
Vineyard Charmer
Distance to beach: 1 mile from Owen Park Beach
Summer:
$1,900 - $2,200/wk
Off Season:
$1,600 - $2,000/wk
Vineyard Haven
ID 31315
Summer:
$2,500 - $2,700/wk
Off Season:
$2,250 - $2,500/wk

Vineyard Haven vacation rentals that sleep 4

Vineyard Haven
ID 31044
Summer:
$1,600 - $1,700/wk
Off Season:
$800 - $1,700/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: Owen Park Beach, Appx. 3/4 mile from house.
Summer:
$2,000 - $2,500/wk
Off Season:
$200 - $400/night
$1,000 - $1,900/wk
$3,500 - $4,000/mo
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
4 reviews read reviews
Summer:
$900 - $1,050/wk
Off Season:
$900 - $950/wk
Vineyard Haven
ID 7848
Summer:
$1,195 - $1,295/wk
Off Season:
$795 - $1,195/wk
Vineyard Haven
ID 29576
Summer:
$1,500 - $1,800/wk
Off Season:
$1,300 - $1,400/wk
Vineyard Haven
ID 7718
1 BR
1 bath
Sleeps 4
Waterview of Vineyard Sound, sleeps 4.
Waterview of Vineyard Sound, sleeps 4.
Distance to beach: 10 minute walk to Owen Little Way Beach.
2 reviews read reviews
Summer:
$1,350/wk
$5,000 - $6,000/mo
Off Season:
$1,200/wk
$800 - $1,000/mo

Vineyard Haven vacation rentals that sleep 2

Vineyard Haven
ID 30012
1 BR
1 bath
Sleeps 2
The Mermaid Suite
The Mermaid Suite
Distance to beach: 8/10 Mile to Owen Park Beach
5 reviews read reviews
Summer:
$200 - $316/night
$1,139 - $2,161/wk
Off Season:
$104 - $225/night
$585 - $1,002/wk