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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.

61 Vacation Properties in Vineyard Haven

Vineyard Haven vacation rentals that sleep 15

Vineyard Haven
ID 29608
5 BR
2 ½ baths
Sleeps 15
Waterfront home steps to Vineyard Sound & Tashmoo Pond
Waterfront home steps to Vineyard Sound & Tashmoo Pond
Distance to beach: Vineyard Sound & Tashmoo Pond - steps to both
Summer:
$12,000 - $17,000/wk
Off Season:
$12,000 - $17,000/wk

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven
ID 27594
5 BR
2 ½ baths
Sleeps 14
Main House near Lagoon & Town (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:
$750/night
$3,000 - $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:
$2,500 - $3,000/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
$2,030 - $4,725/wk
Vineyard Haven
ID 16690
Summer:
$4,800 - $5,300/wk
Off Season:
$3,200 - $4,000/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:
$4,000 - $6,000/wk
Off Season:
$700 - $850/night
$2,500 - $4,000/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:
$720 - $1,117/night
$5,041 - $7,818/wk
Off Season:
$282 - $725/night
$1,971 - $5,078/wk
Tisbury
ID 26357
4 BR
2 baths
Sleeps 10
Charming Four bedroom, close to Ferry
Charming Four bedroom, close to Ferry
Distance to beach: .75 mile Owen Park Beach
Summer:
$3,000/wk
Off Season:
$2,500/wk
Vineyard Haven
ID 28968
Summer:
$8,500 - $10,000/wk
Off Season:
$8,500/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 to outer harbor beach; 1.3 to Lake Tashm
6 reviews read reviews
Summer:
$1,800 - $2,800/wk
Off Season:
$1,800 - $2,300/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
OWNER SPECIAL:
Price reduction of $500 on choice summer weeks. Book now!
Summer:
$3,500 - $5,000/wk
Off Season:
$750 - $3,750/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: Owen Park Beach 1/2 mile
OWNER SPECIAL:
Limited Transferable Ferry Tickets available for car.
Summer:
$1,000 - $1,285/night
$7,000 - $9,000/wk
Off Season:
$650/night
$4,550 - $7,000/wk

Vineyard Haven vacation rentals that sleep 8

Vineyard Haven
ID 3014
4 BR
2 baths
Sleeps 8
Charming home in quiet neighborhood of Vineyard Haven
Charming home in quiet neighborhood of Vineyard Haven
Distance to beach: 1 mile to Lake Tashmoo, or 1 mile to Owens Beach
2 reviews read reviews
Summer:
$1,800 - $2,600/wk
Off Season:
$1,800/wk
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
2 reviews read reviews
OWNER SPECIAL:
Free Auto Reservations for July 29 - August 5th week.
Summer:
$5,000 - $8,990/wk
Off Season:
$715/night
$5,000 - $8,490/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
OWNER SPECIAL:
"GREAT LOCATION" WEEKS ARE STILL AVAILABLE FOR JULY & AUGUST. BOOK NOW BEFORE THEY ARE GONE...
Summer:
$4,000 - $5,500/wk
Off Season:
$500 - $800/night
$4,000 - $5,500/wk
Vineyard Haven
ID 28257
4 BR
3 ½ baths
Sleeps 8
PICTURESQUE WALK TO BEACH, SLEEPS 4!
PICTURESQUE WALK TO BEACH, SLEEPS 4!
Distance to beach: Tashmoo Beach 1 Mile
Summer:
$4,000 - $7,250/wk
Off Season:
$4,000 - $4,700/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
2 reviews read reviews
OWNER SPECIAL:
Memorial Day Special! Weekly rental reduced to $3,999!!! Week of June 3 reduced to $3,999!!!
Summer:
$5,990 - $8,990/wk
Off Season:
$700 - $1,000/night
$2,990 - $4,990/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: 1/4 mile to Owen Park Beach.
Summer:
$2,900 - $3,900/wk
$8,500 - $12,000/mo
Off Season:
$2,900/wk
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: State Beach 3 miles
OWNER SPECIAL:
Rates Reduced on available weeks. FERRY TICKETS avail for purchase weeks 7/22; 7/29.
Summer:
$1,900 - $2,700/wk
Off Season:
$1,900/wk
Vineyard Haven
ID 30055
Summer:
$4,000 - $5,500/wk
Off Season:
$4,000 - $5,500/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.
OWNER SPECIAL:
CHARMING HOUSE. NEW LISTING. JULY AND AUGUST ROUND TRIP FERRY TICKETS AVAILABLE.
Summer:
$4,500 - $5,500/wk
Off Season:
$3,000 - $5,000/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
9 reviews read reviews
Summer:
$2,000 - $2,850/wk
$10,500/mo
Off Season:
$150 - $350/night
$2,000 - $2,500/wk
$4,000 - $7,000/mo
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
Summer:
$2,500 - $3,000/wk
Off Season:
$2,000 - $2,800/wk
Vineyard Haven
ID 21913
3 BR
2 baths
Sleeps 8
Rent a Cozy House in Vineyard Haven
Rent a Cozy House in Vineyard Haven
Distance to beach: Owen Park Beach 5 minutes; Tisbury Town Beach 10 m
Summer:
$2,000 - $2,200/wk
Off Season:
$150 - $200/night
$1,800/wk
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
3 reviews read reviews
Summer:
$2,500 - $2,650/wk
Off Season:
$300/night
$1,500 - $1,850/wk
Vineyard Haven
ID 28707
3 BR
3 baths
Sleeps 8
Bright, Spacious Tashmoo Wood Condo
Bright, Spacious Tashmoo Wood Condo
Distance to beach: Private Association Lake Tashmoo less than 1 mile
Summer:
$2,800 - $3,000/wk
Off Season:
$250/night
$1,750 - $3,000/wk
Vineyard Haven
ID 29178
3 BR
3 baths
Sleeps 8
Vineyard Haven Gem - A perfect back drop for making memories
Vineyard Haven Gem - A perfect back drop for making memories
Distance to beach: 10 min walk to Owen Park Beach
OWNER SPECIAL:
JULY FERRY TICKETS AVAILABLE.
Summer:
$571 - $642/night
$3,500 - $5,000/wk
Off Season:
$357 - $500/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
Summer:
$4,495 - $6,495/wk
Off Season:
$700/night
$3,500 - $4,995/wk

Vineyard Haven vacation rentals that sleep 7

Vineyard Haven
ID 3755
4 BR
1 ½ bath
Sleeps 7
Right on the water
Right on the water
Distance to beach: about 30 feet. You are right there.
3 reviews read reviews
Summer:
$2,500 - $3,300/wk
Off Season:
$150 - $400/night
$850 - $2,700/wk
Vineyard Haven
ID 29593
4 BR
2 ½ baths
Sleeps 7
Great Location - Walk to Town & Beach - Family Friendly
Great Location - Walk to Town & Beach - Family Friendly
Distance to beach: 3 blocks to Town beach at Owen Little Way
4 reviews read reviews
Summer:
$2,000 - $3,350/wk
Off Season:
$285/night
$2,000/wk
Vineyard Haven
ID 16365
2 BR
3 baths
Sleeps 7
Tashmoo Woods Condo
Tashmoo Woods Condo
Distance to beach: 1.5 mi to Lake Tashmoo Town Beach (Herring Creek)
Summer:
$300 - $400/night
$2,000 - $2,800/wk
$9,000 - $12,000/mo
Off Season:
$250 - $400/night
$1,500 - $2,500/wk
$4,000 - $7,000/mo

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:
$2,200 - $2,300/wk
Off Season:
$1,500 - $2,300/wk
$1,200/mo
Vineyard Haven
ID 15230
Summer:
$2,200 - $2,300/wk
Off Season:
$1,600 - $2,000/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
Summer:
$2,200 - $2,600/wk
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
7 reviews read reviews
Summer:
$2,600 - $3,300/wk
Off Season:
$2,600/wk
$2,500 - $3,000/mo
Vineyard Haven
ID 27296
3 BR
1 ½ bath
Sleeps 6
Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!
Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!
Distance to beach: Lake Tashmoo, Owen Park, Wilfred's Pond
Summer:
$2,200/wk
Off Season:
$1,900 - $2,200/wk
Vineyard Haven
ID 27956
3 BR
2 ½ baths
Sleeps 6
Summer fun begins with a great vacation home and this is one
Summer fun begins with a great vacation home and this is one
Distance to beach: Eastville Beach 2 miles away
OWNER SPECIAL:
Transferable Ferry ticket available for the week of July 28th.
Summer:
$2,400 - $2,700/wk
Off Season:
$1,850 - $2,700/wk
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:
$2,800 - $3,000/wk
Off Season:
$2,500 - $2,800/wk
Vineyard Haven
ID 24544
3 BR
2 baths
Sleeps 6
Walk to the Village
Walk to the Village
Distance to beach: 2 miles to Eastville Beach, walk to VH Harbor
Summer:
$2,800/wk
Off Season:
$2,800/wk
Tisbury
ID 28404
3 BR
2 baths
Sleeps 6
Charming 3 Bedroom 2 Bathroom Cape Cod
Charming 3 Bedroom 2 Bathroom Cape Cod
Distance to beach: 1 Mile to Town Beach
Summer:
$2,400/wk
Off Season:
$2,400/wk
Vineyard Haven
ID 29326
Summer:
$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:
$404 - $1,044/night
$2,826 - $7,308/wk
Off Season:
$166 - $679/night
$1,159 - $4,755/wk
Vineyard Haven
ID 30347
3 BR
2 ½ baths
Sleeps 6
Treehouse
Treehouse
Distance to beach: less than a mile to Owen Park Beach
5 reviews read reviews
Summer:
$2,550 - $3,000/wk
$10,000/mo
Off Season:
$350/night
$2,500 - $2,550/wk
$8,000 - $9,500/mo
Vineyard Haven
ID 6517
3 BR
1 bath
Sleeps 6
Ocean Front and Lake Front Cottage
Ocean Front and Lake Front Cottage
Distance to beach: private ocean beach and private lakefront beach
Summer:
$5,000 - $6,000/wk
Off Season:
$4,000 - $6,000/wk
$20,000/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:
$1,200 - $1,800/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:
$3,100 - $3,300/wk
Off Season:
$2,100 - $2,800/wk
Vineyard Haven
ID 26940
2 BR
1 bath
Sleeps 6
2 Bedroom Cottage on Beautiful Hines Point
2 Bedroom Cottage on Beautiful Hines Point
Distance to beach: Eastville Beach is 1 1/2 miles from cottage
1 review read review
Summer:
$2,000 - $2,750/wk
Off Season:
$2,000/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 - $422/night
$1,617 - $2,954/wk
Off Season:
$132 - $305/night
$924 - $2,138/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
Summer:
$3,000/wk
Off Season:
$300/night
$2,100/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
Off of Franklin Street
ID 28312
3 BR
1 ½ bath
Sleeps 5
Clean Cape - Close to Town
Clean Cape - Close to Town
Distance to beach: Town Beach 1 mile
Summer:
$1,600/wk
Off Season:
$1,600/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
30 reviews read reviews
Summer:
$1,600 - $1,800/wk
Off Season:
$250/night
$1,200 - $1,600/wk
$1,200 - $1,500/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:
$2,100 - $2,300/wk
Off Season:
$350/night
$1,900 - $2,300/wk

Vineyard Haven vacation rentals that sleep 4

Vineyard Haven
ID 29639
2 BR
1 bath
Sleeps 4
Private, Updated West Chop Guesthouse
Private, Updated West Chop Guesthouse
Distance to beach: Tashmoo Beach - 1.5 mi, Owen Little Beach - 1.2 mi
Summer:
$1,250 - $1,550/wk
$6,000 - $6,500/mo
Off Season:
$1,000 - $1,550/wk
$1,500 - $5,500/mo
Vineyard Haven
ID 7848
Summer:
$1,095 - $1,295/wk
Off Season:
$795 - $1,095/wk
Vineyard Haven
ID 29576
Summer:
$1,300 - $1,700/wk
Off Season:
$1,000 - $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
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:
$850 - $1,000/wk
Off Season:
$850/wk

Vineyard Haven vacation rentals that sleep 2

Vineyard Haven
ID 27158
Summer:
$1,000 - $1,400/wk
Off Season:
$250/night
$900 - $1,000/wk
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:
$162 - $323/night
$1,132 - $2,258/wk
Off Season:
$85 - $231/night
$596 - $1,619/wk
Vineyard Haven
ID 29999
1 BR
1 bath
Sleeps 2
Sea Captain's Victorian w. Studio ~ pets welcome
Sea Captain's Victorian w. Studio ~ pets welcome
Distance to beach: Owen Park Beach is 5/10 mile
Summer:
$150/night
$1,100/wk
Off Season:
$150/night
$1,100/wk