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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.

49 Vacation Properties in Vineyard Haven
Sleeps

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven
ID 27594
5 BR
3 ½ baths
Sleeps 14
Main House near Lagoon & Town (SLEEPS 14)
Main House near Lagoon & Town (SLEEPS 14)
Distance to beach: 4 miles State Beach and Less than one mile to Lagoon Beach via wooded hike
Summer:
$5,500 - $6,200/wk
Off Season:
$500 - $900/night
$3,500 - $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 - $4,500/wk
$17,000 - $18,000/mo
Off Season:
$2,500 - $3,000/wk
$10,000 - $11,500/mo
Vineyard Haven
ID 32917
7 BR
5 baths
Sleeps 12
Wonderful for families! Walk to beach and to town!
Wonderful for families! Walk to beach and to town!
Distance to beach: 1/2 mile to Owen Park Beach and Beach access via our street.
Summer:
$8,000 - $10,500/wk
$38,000 - $42,000/mo
Off Season:
$800 - $1,000/night
$2,500 - $7,500/wk
$6,000 - $18,000/mo
Vineyard Haven
ID 30881
Summer:
$6,500 - $6,800/wk
Off Season:
$6,500/wk

Vineyard Haven vacation rentals that sleep 10

Vineyard Haven
ID 16690
Summer:
$5,500 - $5,900/wk
Off Season:
$5,500/wk
Vineyard Haven
ID 29492
5 BR
2 baths
Sleeps 10
Amazing Lake & Ocean Views, Private Beach, Great for Kayaks
Amazing Lake & Ocean Views, Private Beach, Great for Kayaks
Distance to beach: Private beach on the property, 3/10 mile to Wilfri
13 reviews read reviews
Summer:
$549 - $849/night
$3,651 - $5,646/wk
Off Season:
$299 - $549/night
$1,988 - $3,983/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:
$4,844 - $7,211/wk
Off Season:
$2,622 - $5,667/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
Off Season:
$750 - $850/night
$3,000 - $5,000/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
10 reviews read reviews
Summer:
$3,850/wk
Off Season:
$500 - $525/night
$3,500/wk
Vineyard Haven
ID 29874
4 BR
4 baths
Sleeps 10
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:
$5,950 - $10,500/wk
Off Season:
$500 - $800/night
$3,500 - $5,600/wk

Vineyard Haven vacation rentals that sleep 9

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 Outer Harbor beach; 1.3 to Lake Tashmoo
8 reviews read reviews
Summer:
$2,000 - $3,000/wk
Off Season:
$1,500 - $2,000/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
2 reviews read reviews
Summer:
$3,250 - $5,000/wk
Off Season:
$1,250 - $3,000/wk

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
4 reviews read reviews
Summer:
$5,500 - $8,990/wk
Off Season:
$785/night
$5,500/wk
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:
$5,500 - $6,500/wk
$5,500 - $6,500/mo
Off Season:
$4,500 - $5,000/wk
$5,000 - $5,500/mo
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
3 reviews read reviews
OWNER SPECIAL:
**We can provide vehicle FERRY TICKET for week of July 19, July 26 and August 2nd bookings!!**.
Summer:
$5,990 - $7,990/wk
Off Season:
$400 - $700/night
$2,990 - $5,990/wk
Martha's Vineyard
ID 29569
4 BR
2 ½ baths
Sleeps 8
Perfect Vineyard Vaca with Central AC, 4 Bedrooms, 2.5 Baths
Perfect Vineyard Vaca with Central AC, 4 Bedrooms, 2.5 Baths
Distance to beach: Owen Park Beach 1 mile
2 reviews read reviews
OWNER SPECIAL:
Ferry Tickets available for purchase July weeks and week of 8/23.
Summer:
$2,975 - $3,575/wk
Off Season:
$2,275 - $2,975/wk
Vineyard Haven
ID 30205
Summer:
$4,800 - $6,000/wk
Off Season:
$400 - $600/night
$4,500 - $5,000/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:
$2,950 - $4,950/wk
West Chop
ID 32778
Summer:
$9,000 - $17,000/wk
Off Season:
$7,000 - $11,000/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
1 review read review
Summer:
$6,000/wk
Vineyard Haven
ID 32425
4 BR
3 ½ baths
Sleeps 8
Newly Renovated Victorian - in town Vineyard Haven
Newly Renovated Victorian - in town Vineyard Haven
Distance to beach: 9/10 mile to Tisbury Town Beach
Off Season:
$7,500/wk
Vineyard Haven
ID 3110
3 BR
2 baths
Sleeps 8
Charming Vacation Home w/ AC ***NEW AMENITIES IN 2020***
Charming Vacation Home w/ AC ***NEW AMENITIES IN 2020***
Distance to beach: 1 mile to Owen Pk Beach, 1.5 miles to Lake Tashmoo
5 reviews read reviews
OWNER SPECIAL:
Round trip vehicle transfer included in rate for weeks of June 21st & August 30th, 2020.
Summer:
$2,500 - $3,150/wk
Off Season:
$300/night
$1,700 - $2,500/wk
Vineyard Haven
ID 29178
Summer:
$5,000 - $6,500/wk
Off Season:
$350 - $500/night
$3,000 - $3,500/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:
$5,995 - $8,495/wk
Off Season:
$643/night
$4,000 - $5,495/wk
Tisbury
ID 33254
3 BR
2 ½ baths
Sleeps 8
Beautifully appointed townhouse; pool, tennis lake for kayak
Beautifully appointed townhouse; pool, tennis lake for kayak
Distance to beach: 1 mile To Owen Park Beach and Tashmoo Beach
Summer:
$3,500 - $4,900/wk
Off Season:
$350 - $450/night
$2,450 - $3,500/wk

Vineyard Haven vacation rentals that sleep 7

Vineyard Haven
ID 29593
4 BR
2 ½ baths
Sleeps 7
Family friendly - Walk to Town & Beach
Family friendly - Walk to Town & Beach
Distance to beach: 2 blocks to Town beach at Owen Little Way
6 reviews read reviews
Summer:
$2,000 - $3,350/wk
Off Season:
$1,575 - $2,000/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:
$2,340 - $2,550/wk
Off Season:
$334/night
$2,340/wk
Vineyard Haven
ID 15230
Summer:
$1,800 - $2,300/wk
Off Season:
$215 - $230/night
$1,500 - $1,800/wk
Vineyard Haven
ID 6517
3 BR
1 bath
Sleeps 6
Oceanfront & Lakefront Home
Oceanfront & Lakefront Home
Distance to beach: private ocean beach and private lakefront beach
1 review read review
Summer:
$6,000/wk
Off Season:
$5,000 - $6,000/wk
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:
$2,000 - $2,200/wk
Off Season:
$200 - $250/night
$900 - $1,800/wk
$1,800 - $2,400/mo
Vineyard Haven
ID 28135
3 BR
2 baths
Sleeps 6
Beautiful Tashmoo Woods Condo w/Central AC
Beautiful Tashmoo Woods Condo w/Central AC
Distance to beach: Tashmoo Woods Assn Beach approx 1/2 mile
Summer:
$3,000/wk
Off Season:
$2,500/wk
Vineyard Haven
ID 25846
3 BR
2 ½ baths
Sleeps 6
Vacation Home Close to Town, Golf and Beach
Vacation Home Close to Town, Golf and Beach
Distance to beach: 1 mile to Tashmoo Beach & Wilfrid's Pond Preserve
Summer:
$3,800/wk
Off Season:
$3,000 - $3,500/wk
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:
$6,815 - $8,909/wk
Off Season:
$1,637 - $6,663/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
7 reviews read reviews
Summer:
$2,500 - $3,000/wk
$8,000 - $10,000/mo
Off Season:
$285 - $425/night
$1,400 - $2,500/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:
$3,300 - $3,500/wk
Off Season:
$2,300 - $3,100/wk
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:
$2,400 - $2,800/wk
Off Season:
$1,000 - $2,500/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:
$2,522 - $3,137/wk
Off Season:
$800 - $2,598/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 Tisbury Town Beach and 1/2 mile to Owen Park beach on Harbor
35 reviews read reviews
Summer:
$1,800/wk
Off Season:
$1,300 - $1,600/wk
$1,200 - $1,300/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:
$2,000 - $2,500/wk
Off Season:
$2,000 - $2,200/wk

Vineyard Haven vacation rentals that sleep 4

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:
$3,250/wk
Off Season:
$2,250 - $3,250/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.
Summer:
$350 - $450/night
$1,750 - $2,750/wk
$9,400 - $10,900/mo
Off Season:
$200 - $450/night
$1,200 - $2,100/wk
$1,500 - $9,400/mo
Vineyard Haven
ID 31044
Summer:
$1,800 - $2,000/wk
Off Season:
$1,200 - $1,500/wk
Vineyard Haven
ID 31287
Summer:
$1,200 - $1,800/wk
Off Season:
$800 - $1,600/wk
$1,200 - $1,600/mo
Vineyard Haven
ID 29639
2 BR
1 bath
Sleeps 4
Private West Chop Guesthouse
Private West Chop Guesthouse
Distance to beach: Tashmoo Beach - 1.5 mi, Owen Little Beach - 1.2 mi
Summer:
$2,500 - $2,800/wk
$10,000/mo
Off Season:
$2,000 - $2,250/wk
$8,000 - $10,000/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
5 reviews read reviews
Summer:
$950 - $1,050/wk
Off Season:
$950/wk
Vineyard Haven
ID 29576
Summer:
$1,500 - $1,900/wk
Off Season:
$1,300 - $1,500/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
Off Season:
$1,300 - $1,400/wk

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:
$2,223 - $2,725/wk
Off Season:
$104 - $225/night
$925 - $2,183/wk