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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.

59 Vacation Properties in Vineyard Haven

Vineyard Haven vacation rentals that sleep 18

Vineyard Haven
ID 37866
9 BR
6 ½ baths
Sleeps 18
Historic Captain's House/Sleeps 18/Walk to Ferry & Beaches
Historic Captain's House/Sleeps 18/Walk to Ferry & Beaches
Distance to beach: 1/2 mi to Eastville Beach and across the street from Owen Park Beach
Summer:
$12,000 - $26,000/wk
Off Season:
$2,500 - $3,000/night
$6,000 - $12,000/wk
5

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven
ID 34385
Summer:
$10,000 - $12,500/wk
Off Season:
$5,000 - $9,000/wk
3

Vineyard Haven vacation rentals that sleep 13

West Chop Waterfront
ID 38244
6 BR
3 baths
Sleeps 13
West Chop Waterfront Home with Private Beach
West Chop Waterfront Home with Private Beach
Distance to beach: Private sandy beach
Summer:
$17,500 - $20,500/wk
Off Season:
$5,000 - $10,000/wk
Vineyard Haven
ID 27594
5 BR
2 ½ baths
Sleeps 13
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 - $7,500/wk
Off Season:
$500 - $900/night
$4,500 - $6,500/wk
5

Vineyard Haven vacation rentals that sleep 12

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:
$18,000 - $28,000/wk
Off Season:
$12,000 - $28,000/wk
VINEYARD HAVEN
ID 35577
5 BR
4 ½ baths
Sleeps 12
Reunion House - Car & Ferry Tkt Available
Reunion House - Car & Ferry Tkt Available
Distance to beach: 2.2 mi to Lake Tashmoo Town Beach
6 reviews read reviews
Summer:
$7,800 - $11,750/wk
$34,000/mo
Off Season:
$3,000 - $8,725/wk
$25,000 - $32,000/mo
9

Vineyard Haven vacation rentals that sleep 10

Waterfront in Vineyard Haven
ID 38336
6 BR
4 ½ baths
Sleeps 10
Vineyard Haven Waterfront with Mooring
Vineyard Haven Waterfront with Mooring
Distance to beach: 0.2 mi to Eastville Beach and water access from the house
Summer:
$18,500 - $20,000/wk
Off Season:
$18,500/wk
Vineyard Haven
ID 16690
Summer:
$7,400/wk
Off Season:
$5,900/wk
3
Vineyard Haven
ID 36252
5 BR
3 ½ baths
Sleeps 10
In town Captain house with double lot garden
In town Captain house with double lot garden
Distance to beach: 0.4 mi to Tisbury Town Beach
4 reviews read reviews
Summer:
$8,000 - $9,500/wk
Off Season:
$7,000 - $8,500/wk
6
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
19 reviews read reviews
Summer:
$4,500/wk
5
Off Main Street
ID 33483
Summer:
$6,000 - $7,500/wk
Off Season:
$6,000 - $7,500/wk
2
Vineyard Haven
ID 38773
4 BR
3 baths
Sleeps 10
Fabulous 4 bedroom in Vineyard Haven
Fabulous 4 bedroom in Vineyard Haven
Distance to beach: 1.7 mi to Tisbury Town Beach
Summer:
$5,900 - $6,400/wk
Off Season:
$5,900/wk

Vineyard Haven vacation rentals that sleep 9

Vineyard Haven
ID 35172
Summer:
$5,000 - $8,000/wk
Off Season:
$3,200 - $5,000/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
6 reviews read reviews
Summer:
$5,000 - $6,500/wk
Off Season:
$2,500 - $4,000/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:
$12,000 - $20,000/wk
Off Season:
$1,000 - $1,800/night
$7,000 - $10,000/wk
2
In the heart of the Village of
ID 32425
4 BR
3 ½ baths
Sleeps 9
Historic Captains Home - Downtown Vineyard Haven
Historic Captains Home - Downtown Vineyard Haven
Distance to beach: 3/10 mile to Tisbury Town Beach and Walk to Owen Park Beach
Summer:
$5,500 - $8,500/wk
Off Season:
$400 - $571/night
$2,800 - $6,500/wk
7
VIneyard Haven
ID 37130
4 BR
2 ½ baths
Sleeps 9
Updated Vineyard Farmhouse - Walk to Town & Ferry
Updated Vineyard Farmhouse - Walk to Town & Ferry
Distance to beach: 1.0 mi to Tisbury Town Beach and 0.7 mi to Owen Park Beach
Summer:
$5,250 - $6,125/wk
Off Season:
$350 - $550/night
$2,450 - $4,165/wk

Vineyard Haven vacation rentals that sleep 8

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:
$4,400 - $4,950/wk
Off Season:
$650 - $750/night
$3,900/wk
5
Martha's Vineyard
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 - $9,450/wk
Off Season:
$750 - $1,000/night
$5,250 - $7,990/wk
4
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:
$1,100 - $1,800/night
$6,000 - $9,000/wk
Off Season:
$714 - $1,000/night
$5,000 - $7,000/wk
Vineyard Haven
ID 36965
4 BR
2 baths
Sleeps 8
Charming, Centrally Located Vineyard Home
Charming, Centrally Located Vineyard Home
Distance to beach: 1 mile Owen Park Beach and 4 miles Oak Bluffs Town Beach
5 reviews read reviews
OWNER SPECIAL:
Summer will be here before you know it! Don't wait until the last minute!
Summer:
$3,500 - $6,000/wk
Off Season:
$2,000 - $3,000/wk
Vineyard Haven (West Chop)
ID 37892
4 BR
2 baths
Sleeps 8
Newly Renovated West Chop/Walk to Beach, Golf, and Ferry
Newly Renovated West Chop/Walk to Beach, Golf, and Ferry
Distance to beach: 1/2 mi to Tisbury Town Beach and 4 mi to Lake Tashmoo Town Beach
3 reviews read reviews
OWNER SPECIAL:
Book 2 weeks and get 10% off.I have ferry tickets!
Summer:
$4,000 - $7,000/wk
Off Season:
$300 - $700/night
$1,500 - $4,500/wk
4
Vineyard Haven
ID 38171
4 BR
3 baths
Sleeps 8
Main Street Charmer
Main Street Charmer
Distance to beach: 0.2 mi to Tisbury Town Beach
Summer:
$2,800 - $4,750/wk
Off Season:
$2,500 - $3,000/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
16 reviews read reviews
OWNER SPECIAL:
Stays of 7 nights or more in Sep/Oct 2024 will receive a round trip vehicle transfer discount!!!
Summer:
$3,400 - $4,200/wk
Off Season:
$450/night
$2,200 - $3,200/wk
3
Vineyard Haven
ID 29178
Summer:
$6,503 - $9,800/wk
Off Season:
$929 - $1,000/night
$6,500 - $6,503/wk
4

Vineyard Haven vacation rentals that sleep 7

Vineyard Haven
ID 29593
4 BR
2 ½ baths
Sleeps 7
Central Air - Walk to Town, Beach & Ferry
Central Air - Walk to Town, Beach & Ferry
Distance to beach: 2/10 mile Tisbury Town Beach and 3/10 Owen Park Beach
12 reviews read reviews
Summer:
$4,500 - $5,600/wk
Off Season:
$1,750 - $4,500/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
2 reviews read reviews
Summer:
$3,800 - $4,800/wk
4
Vineyard Haven
ID 38183
3 BR
2 ½ baths
Sleeps 7
Centrally Located; Brand New Home/Walk to Lagoon
Centrally Located; Brand New Home/Walk to Lagoon
Distance to beach: 1/4 mi to Lagoon; 1.7 mi to Tisbury Town
Summer:
$600 - $700/night
$4,500 - $6,000/wk
Off Season:
$400 - $770/night
$3,150 - $5,500/wk
8

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:
$3,300 - $3,400/wk
Off Season:
$347/night
$2,500 - $3,400/wk
$2,200 - $2,500/mo
Vineyard Haven
ID 15230
Summer:
$2,800 - $3,000/wk
Off Season:
$1,600 - $3,000/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
22 reviews read reviews
Summer:
$4,200 - $6,000/wk
Off Season:
$369 - $649/night
$2,600 - $4,700/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
17 reviews read reviews
Summer:
$3,000 - $5,500/wk
Off Season:
$3,000 - $4,500/wk
3
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!
11 reviews read reviews
Summer:
$7,750 - $12,500/wk
Off Season:
$925 - $1,100/night
$6,750 - $8,000/wk
8
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:
$2,500 - $3,000/wk
Off Season:
$2,500/wk
3
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
OWNER SPECIAL:
Transferrable ferry tickets are available for purchase for select weeks.
Summer:
$3,750 - $5,775/wk
Off Season:
$1,500 - $5,500/wk
4
Vineyard Haven
ID 33882
3 BR
3 baths
Sleeps 6
Vineyard Getaway: Access to Pool, Dock, Trails, & Beaches!
Vineyard Getaway: Access to Pool, Dock, Trails, & Beaches!
Distance to beach: 7/10 mi to Owen Park Beach and 8/10 mile to beautiful Tashmoo Pond and public bea
2 reviews read reviews
Summer:
$4,400 - $4,650/wk
Off Season:
$450 - $550/night
$2,650 - $4,550/wk
2
Tisbury
ID 36737
Summer:
$5,400 - $6,000/wk
Off Season:
$750/night
$4,400 - $5,400/wk
6
Vineyard Haven
ID 37747
3 BR
2 baths
Sleeps 6
Waterfront Classic w/ Private Beach & ferry reservations!
Waterfront Classic w/ Private Beach & ferry reservations!
Distance to beach: Private BEACH on Lagoon Pond is 100 steps
Summer:
$9,000 - $10,000/wk
Off Season:
$9,000/wk
9
Vineyard Haven
ID 37831
3 BR
3 baths
Sleeps 6
Vineyard Haven Townhouse with Pool
Vineyard Haven Townhouse with Pool
Distance to beach: 1.2 mi to Eastville Beach
Summer:
$2,880 - $3,500/wk
Off Season:
$343/night
$2,400 - $3,000/wk
Vineyard Haven
ID 37838
3 BR
2 baths
Sleeps 6
Wedding guest romantic weekend girls trip golf fishing
Wedding guest romantic weekend girls trip golf fishing
Distance to beach: 8/10 mile to Tisbury Town Beach and 2.2 Lake Tashmoo Town Beach
3 reviews read reviews
Summer:
$4,800 - $5,800/wk
Off Season:
$560 - $600/night
$3,500 - $4,800/wk
4
Vineyard Haven
ID 37651
3 BR
2 baths
Sleeps 6
Great Location/Walk to Lake Tashmoo and Tennis
Great Location/Walk to Lake Tashmoo and Tennis
Distance to beach: 1.3 mi to Tisbury Town Beach
Summer:
$3,200 - $4,000/wk
Off Season:
$275 - $400/night
$2,800 - $3,200/wk
5
VIneyard Haven
ID 35985
Off Season:
$300 - $365/night
2
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:
$2,500 - $3,300/wk
Off Season:
$2,300 - $3,000/wk
4
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:
$3,900 - $5,400/wk
Off Season:
$2,900 - $4,000/wk

Vineyard Haven vacation rentals that sleep 5

Vineyard Haven
ID 7366
Summer:
$3,350/wk
Off Season:
$2,512 - $3,350/wk
2
Vineyard Haven
ID 29565
2 BR
2 baths
Sleeps 5
Vineyard Charmer
Vineyard Charmer
Distance to beach: 1 mile Owen Park Beach
Summer:
$3,400/wk
Off Season:
$3,000 - $3,400/wk
2
Vineyard Haven
ID 33784
2 BR
1 bath
Sleeps 5
Summer Cottage - Walk to Town & Water
Summer Cottage - Walk to Town & Water
Distance to beach: 1.3 mi to Tisbury Town Beach
Summer:
$2,700 - $4,150/wk
Off Season:
$1,170 - $2,850/wk
6

Vineyard Haven vacation rentals that sleep 4

Vineyard Haven
ID 19399
3 BR
2 baths
Sleeps 4
Charming Bright Sunny Cape Home in Vineyard Haven
Charming Bright Sunny Cape Home in Vineyard Haven
Distance to beach: 10 min walk Owen Park Beach and Lake Tashmoo Beach, Tisbury Town Beach also close
9 reviews read reviews
Summer:
$1,800 - $2,600/wk
Off Season:
$250/night
$900 - $2,200/wk
$1,400 - $1,700/mo
3
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
45 reviews read reviews
Summer:
$1,800 - $2,000/wk
Off Season:
$250 - $350/night
$1,800 - $2,000/wk
$1,700 - $1,800/mo
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:
$3,400 - $4,600/wk
$13,113 - $19,660/mo
Off Season:
$375 - $750/night
$1,500 - $3,250/wk
$3,500 - $12,258/mo
7
Vineyard Haven
ID 31287
Summer:
$2,000 - $2,100/wk
Off Season:
$1,200 - $2,100/wk
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!
OWNER SPECIAL:
Tax Exempt When Renting 32+ Nights!
Summer:
$3,900 - $5,500/wk
Off Season:
$425 - $650/night
$2,500 - $4,550/wk
$2,800 - $15,000/mo
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: 0.9 mi to Tisbury Town Beach
2 reviews read reviews
Summer:
$2,600 - $3,600/wk
Off Season:
$260 - $2,900/wk
5
VIneyard Haven
ID 36738
Summer:
$4,900 - $5,900/wk
Off Season:
$1,100 - $4,900/wk
$3,500 - $12,000/mo
6
Vineyard Haven
ID 38039
2 BR
2 baths
Sleeps 4
Cozy Cottage in the Woods, Walk to Beach, Bike to Town
Cozy Cottage in the Woods, Walk to Beach, Bike to Town
Distance to beach: 4/10 Mi to Grove Avenue Beach;1 mi Owen Park Beach
Summer:
$3,200 - $4,500/wk
$15,000 - $18,000/mo
Off Season:
$250 - $350/night
$1,750 - $4,000/wk
$7,000 - $13,000/mo
6
Tisbury
ID 38371
Summer:
$2,600 - $3,500/wk
Off Season:
$2,000 - $2,800/wk
4

Vineyard Haven vacation rentals that sleep 2

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:
$1,700/wk
Off Season:
$600 - $1,400/wk
Vineyard Haven
ID 21680
1 BR
1 bath
Sleeps 2
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 - $1,100/wk
Off Season:
$950/wk
Vineyard Haven
ID 29576
Summer:
$2,500 - $3,000/wk
Off Season:
$250 - $400/night