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Martha's Vineyard Vacation Rentals

Vineyard Haven Vacation Rentals

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.

65 properties

Vineyard Haven Guide

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

Distance to beach: 1/2 mi to Eastville Beach and across the street from Owen Park Beach

5.02 reviews

OWNER SPECIAL:

PRICE DROP: $4000 off, 1 week is NOW $20,000 (available weeks 6/28-7/5, 7/5-7/12, and 8/16-8/23).

Summer:
$14,000 - $26,000/wk

Off Season:
$1,500 - $3,000/night
$8,000 - $14,000/wk

Vineyard Haven vacation rentals that sleep 14

Vineyard Haven

ID 34385

7 BR

4 baths

Sleeps 14

Magnificent 7 Bedroom, West Chop, Beachfront, Dock & Tennis!

Distance to beach: Gorgeous Shared Private Beach

Summer:
$1,450 - $2,450/night
$10,250 - $12,250/wk

Off Season:
$900 - $1,500/night
$5,000 - $9,000/wk

Vineyard Haven vacation rentals that sleep 12

Vineyard Haven

ID 39172

6 BR

4 ½ baths

Sleeps 12

Luxurious Six-Bedroom Vineyard Haven Cottage/Walk to Beach

Distance to beach: 1/10 mile to Tisbury Town Beach

5.01 review

Summer:
$9,000 - $14,000/wk

Off Season:
$500 - $800/night
$5,000 - $12,000/wk

Vineyard Haven

ID 21782

6 BR

3 ½ baths

Sleeps 12

Harborfront Home in Vineyard Haven

Distance to beach: Sits on the harbor beach (less than 1/10 of a mi)

Summer:
$5,750 - $6,500/wk
$25,000/mo

Off Season:
$750 - $820/night
$5,750/wk
$18,000/mo

Vineyard Haven

ID 35726

6 BR

6 ½ baths

Sleeps 12

Private Estate with Pool and Tennis

Distance to beach: 2.4 mi to Lake Tashmoo Town Beach

Summer:
$15,000 - $28,000/wk

Off Season:
$15,000 - $22,000/wk

Vineyard Haven

ID 38942

5 BR

6 ½ baths

Sleeps 12

Luxurious Beachfront Haven w/ Private Dock & Views

Distance to beach: Situated on Private Beach

Summer:
$15,000 - $35,000/wk

Off Season:
$1,700 - $2,100/night
$10,000 - $25,000/wk

Vineyard Haven vacation rentals that sleep 11

Waterfront on Vineyard Haven H

ID 38336

6 BR

4 ½ baths

Sleeps 11

West Chop Waterfront/FERRY TICKETS AVAILABLE

Distance to beach: 0.2 mi to Eastville Beach and water access from the house

OWNER SPECIAL:

Waterfront Home Available all of August/FERRY TICKETS for Most Weeks.

Summer:
$17,500 - $18,500/wk

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

Distance to beach: 1 block to Owen Park Beach

5.011 reviews

OWNER SPECIAL:

$1000 off if you rent 2 weeks starting August 23rd.

Summer:
$6,900 - $7,400/wk

Off Season:
$6,900/wk

VINEYARD HAVEN

ID 35577

5 BR

4 ½ baths

Sleeps 10

Reunion House: Car + Ferry Tickets

Distance to beach: 1.5 miles to James Pond Preserve (Lambert's Cove)

5.09 reviews

Summer:
$7,725 - $10,750/wk

Off Season:
$4,000 - $8,000/wk

Vineyard Haven

ID 40173

5 BR

4 baths

Sleeps 10

Luxurious Contemporary Near The Lagoon

Distance to beach: 1.4 mi to Tisbury Town Beach

Summer:
$8,400 - $10,500/wk

Off Season:
$950 - $1,000/night
$5,600 - $8,400/wk

Lower Makonikey, off Lambert's

ID 3695

4 BR

3 baths

Sleeps 10

Secluded 4+br home: short walk to private association beach

Distance to beach: 4/10 mile to private Lower Makonikey Beach

4.919 reviews

OWNER SPECIAL:

Only 1 week available! Prime July week, 7/6-13.

Summer:
$4,500 - $4,600/wk

Vineyard Haven

ID 30546

4 BR

3 baths

Sleeps 10

4-Bedroom Vineyard Haven Home

Distance to beach: 1.2 miles to Owen Park Beach

4.918 reviews

Summer:
$4,500 - $6,500/wk

Off Season:
$400 - $500/night
$3,000 - $5,500/wk

Off Main Street

ID 33483

4 BR

2 baths

Sleeps 10

MV25 Your Island Escape Awaits. Quiet & Relaxing.

Distance to beach: 2/10 mi to Tisbury Town Beach

5.05 reviews

Summer:
$6,000 - $7,500/wk

Off Season:
$3,000 - $6,000/wk

Vineyard Haven vacation rentals that sleep 9

Vineyard Haven

ID 35172

5 BR

3 baths

Sleeps 9

Larrier House; walk to town and a large secret garden

Distance to beach: 1.2 mi to Tisbury Town Beach

Summer:
$5,000 - $8,000/wk

Off Season:
$5,000 - $7,000/wk

Vineyard Haven

ID 18566

4 BR

2 baths

Sleeps 9

Waterfront Cottage with Private Beach

Distance to beach: On the beach

5.06 reviews

OWNER SPECIAL:

Owners special - Price reduction - Save $900/wk for wks of 5.10, 6.21, 6.28 Book now.

Summer:
$5,000 - $6,900/wk

Off Season:
$2,750 - $4,400/wk

Vineyard Haven

ID 29874

4 BR

4 baths

Sleeps 9

Luxury 4 Ensuite Bedrooms, Pool, Spa, Cabana Walk To Town VH

Distance to beach: .5 miles Owen Park Beach and Owen Park Beach 1/2 mile

Summer:
$16,000 - $20,000/wk

Off Season:
$1,000 - $1,800/night
$7,000 - $12,000/wk

VIneyard Haven

ID 37130

4 BR

2 ½ baths

Sleeps 9

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

OWNER SPECIAL:

25% off in Sept.

Summer:
$2,000 - $6,200/wk

Off Season:
$350 - $550/night
$4,200 - $5,500/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

Distance to beach: 1/2 mile to Owen Park Beach and 1/4 mile to Owen Park Beach.

Summer:
$3,510 - $4,950/wk

Off Season:
$3,330/wk

Martha's Vineyard

ID 29569

4 BR

2 ½ baths

Sleeps 8

Perfect Vineyard Vacay with Central AC, 4 Bedrooms, 2.5 Bath

Distance to beach: 3 State Beach

5.09 reviews

OWNER SPECIAL:

FERRY TICKETS + $200 OFF JULY 13th-July20 PLEASE READ ALL REVIEWS THIS IS A SWEET SPOT.

Summer:
$4,675 - $4,975/wk

Off Season:
$4,675 - $4,775/wk

Martha's Vineyard

ID 28424

4 BR

4 ½ baths

Sleeps 8

Captain Spring House: In-town Luxury with Water Views

Distance to beach: 3/10 mile Owen Park Bch, 1/2 mile Town Beach

5.01 review

Summer:
$7,990 - $9,650/wk

Off Season:
$750 - $1,000/night
$5,250 - $7,990/wk

Vineyard Haven

ID 34561

4 BR

2 baths

Sleeps 8

A/C Home w/ Peaceful Pool

Distance to beach: 10 minute walk to Owen's Beach State Park

5.02 reviews

Summer:
$7,000 - $10,000/wk

Off Season:
$5,000 - $7,000/wk

Vineyard Haven

ID 36965

4 BR

2 baths

Sleeps 8

Charming, Centrally Located Vineyard Home

Distance to beach: 1 mile Owen Park Beach and 4 miles Oak Bluffs Town Beach

4.910 reviews

Summer:
$3,500 - $6,000/wk

Off Season:
$2,000 - $3,500/wk
$3,500 - $4,000/mo

Vineyard Haven (West Chop)

ID 37892

4 BR

2 baths

Sleeps 8

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

5.07 reviews

OWNER SPECIAL:

I have ferry reservations for you!

Summer:
$3,500 - $6,500/wk

Off Season:
$1,500 - $4,000/wk

Vineyard Haven

ID 37328

4 BR

2 ½ baths

Sleeps 8

Makonikey with Private Beach Nearby

Distance to beach: 2.0 mi to Lambert's Cove Beach and Half mile to association beach

Summer:
$6,000 - $7,500/wk

Off Season:
$6,000/wk

Vineyard Haven

ID 39883

4 BR

2 ½ baths

Sleeps 8

Red Buoy Hideaway w/ Private In-Law Suite

Distance to beach: 1.6 miles to Owen Park Beach and 2 mi to Lake Tashmoo Town Beach

Summer:
$5,175 - $8,050/wk

Off Season:
$570 - $750/night
$4,025 - $5,750/wk

Vineyard Haven

ID 39177

4 BR

3 baths

Sleeps 8

Private Beachfront Cottage that Has It All

Distance to beach: 0.5 mi to Owen Park Beach and Private beach right in front of the home.

Summer:
$6,000/wk

Off Season:
$250 - $500/night
$5,000/wk

VIneyard Haven

ID 39682

4 BR

2 ½ baths

Sleeps 8

The Bellevue - Stunning 4/2.5 Water View, Hot Tub

Distance to beach: 1.0 mi to Tisbury Town Beach and Under 3 miles to Inkwell Beach, Oak Bluffs

15 reviews

Summer:
$6,900 - $8,400/wk

Off Season:
$399 - $950/night
$2,800 - $6,900/wk
$7,000 - $8,000/mo

Vineyard Haven

ID 3110

3 BR

2 baths

Sleeps 8

Peaceful Escape | Charming Vacation Home w/ AC

Distance to beach: 1.0 mile Owen Park Beach and 1.5 miles Lake Tashmoo Town Beach

5.016 reviews

Summer:
$4,200/wk

Off Season:
$450 - $500/night
$2,200 - $3,400/wk

Vineyard Haven

ID 29178

3 BR

3 baths

Sleeps 8

Vineyard Haven Gem - A perfect back drop for making memories

Distance to beach: 10 min walk to Owen Park Beach

5.010 reviews

Summer:
$6,503 - $9,800/wk

Off Season:
$786 - $929/night
$5,502 - $9,800/wk

Vineyard Haven

ID 36073

3 BR

3 baths

Sleeps 8

Private Setting with Two Private Beaches (Select Ferry Tix)

Distance to beach: 1/4 mile to Private Association Beach

6 reviews

Summer:
$6,825/wk

Off Season:
$4,200 - $6,650/wk

Vineyard Haven

ID 40043

3 BR

3 baths

Sleeps 8

Serene Location Yet Only Minutes to Downtown Vineyard Haven

Distance to beach: 1.9 mi to Tisbury Town Beach

OWNER SPECIAL:

Aug 10th and Aug 17th NOW AVAILABLE!

Summer:
$5,200 - $6,200/wk

Off Season:
$550 - $890/night
$4,900 - $5,900/wk

Vineyard Haven vacation rentals that sleep 7

Vineyard Haven

ID 29593

4 BR

2 ½ baths

Sleeps 7

Charming - Family Friendly - A/C - Walk to Town/Beach/Ferry

Distance to beach: 2/10 mile Tisbury Town Beach and 3/10 Owen Park Beach

4.812 reviews

Summer:
$4,200 - $5,600/wk

Off Season:
$2,450 - $4,200/wk

Downtown Vineyard Haven

ID 29406

3 BR

3 ½ baths

Sleeps 7

MV Modern Farmhouse

Distance to beach: A few blocks to Owen Park Beach

5.02 reviews

Summer:
$4,995 - $12,500/wk

Off Season:
$4,500 - $5,995/wk

Vineyard Haven

ID 35457

3 BR

1 bath

Sleeps 7

Family Home Close to Downtown

Distance to beach: 1/2 mi to Owen Park Beach

4.85 reviews

Summer:
$3,800 - $5,000/wk

Vineyard Haven vacation rentals that sleep 6

Vineyard Haven

ID 16365

3 BR

3 baths

Sleeps 6

Tashmoo Wood Condo

Distance to beach: 1.5 mi to Lake Tashmoo Town Beach (Herring Creek)

Summer:
$2,500 - $3,400/wk

Off Season:
$2,000 - $3,400/wk

Vineyard Haven

ID 29492

3 BR

2 baths

Sleeps 6

Amazing Views Year-Round, Private Beach, Great for Kayaking

Distance to beach: Private beach on the property, 3/10 mile to public

5.031 reviews

Summer:
$4,150 - $6,100/wk

Off Season:
$329 - $659/night
$2,250 - $4,700/wk

Vineyard Haven

ID 33283

3 BR

1 ½ bath

Sleeps 6

Commanding Lagoon Waterfront, Private Beach: 180° View

Distance to beach: 20 ft from the your own 250' private Lagoon Beach!

5.013 reviews

Summer:
$7,750 - $12,500/wk

Off Season:
$925 - $1,000/night
$4,500 - $8,500/wk

Vineyard Haven

ID 27296

3 BR

1 ½ bath

Sleeps 6

Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!

Distance to beach: Lake Tashmoo, Owen Park, Wilfred's Pond

Summer:
$2,600 - $2,900/wk

Off Season:
$2,600/wk

Vineyard Haven

ID 34233

3 BR

1 ½ bath

Sleeps 6

Historic, Renovated, In Town Cape

Distance to beach: 1.0 mi to Tisbury Town Beach

5.04 reviews

Summer:
$3,850 - $5,775/wk

Off Season:
$350 - $550/night
$2,100 - $4,550/wk

Tisbury

ID 36737

3 BR

2 ½ baths

Sleeps 6

Walk to Town Beach, Downtown, Sunny Stylish VH Ranch

Distance to beach: one block Tisbury Town Beach

Summer:
$5,400 - $6,000/wk
$26,000 - $29,000/mo

Off Season:
$5,400 - $5,600/wk
$12,000 - $22,000/mo

Vineyard Haven

ID 37838

3 BR

2 baths

Sleeps 6

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

5.04 reviews

Summer:
$3,800 - $5,800/wk

Off Season:
$3,500/wk

Vineyard Haven

ID 37651

3 BR

2 baths

Sleeps 6

Great Location/Walk to Lake Tashmoo and Tennis

Distance to beach: 1.3 mi to Tisbury Town Beach

Summer:
$3,000 - $4,500/wk

Off Season:
$300 - $400/night
$3,000 - $3,500/wk

Vineyard Haven

ID 39147

3 BR

2 baths

Sleeps 6

Renovated Home Near Town Vineyard Haven

Distance to beach: 2.1 mi to Tisbury Town Beach

Summer:
$4,500 - $6,000/wk

Off Season:
$500 - $1,000/night
$4,000 - $4,500/wk

Vineyard Haven

ID 39473

3 BR

2 baths

Sleeps 6

Renovated Vineyard Retreat: Modern & Convenient Location

Distance to beach: 1.7 mi to Tisbury Town Beach

Summer:
$565/night
$3,600 - $4,000/wk
$12,650 - $15,000/mo

Off Season:
$299/night
$2,000 - $4,000/wk
$7,000 - $13,000/mo

Vineyard Haven

ID 11693

3 BR

2 baths

Sleeps 6

Charming Cottage near West Chop- Vineyard Haven

Distance to beach: 2 Blks to Owen Little Beach-1 mi. to Tashmoo Beach

5.05 reviews

Summer:
$3,250 - $3,465/wk

Off Season:
$3,000 - $3,465/wk
$2,600 - $11,000/mo

Vineyard Haven

ID 37747

3 BR

2 baths

Sleeps 6

Waterfront Classic w/Private Beach.Kayaks & Paddle Boards

Distance to beach: Private BEACH on Lagoon Pond is 100 steps

2 reviews

Summer:
$9,800/wk

Vineyard Haven

ID 4482

2 BR

1 bath

Sleeps 6

Hine's Point Waterfront

Distance to beach: 1/2 mile

5.01 review

Summer:
$3,900 - $5,600/wk

Off Season:
$3,600 - $4,300/wk

Vineyard Haven

ID 26940

2 BR

1 bath

Sleeps 6

2 Bedroom Cottage on Beautiful Hines Point

Distance to beach: Eastville Beach is 1 1/2 miles from cottage

5.01 review

Summer:
$5,000/wk

Off Season:
$4,000/wk

Vineyard Haven

ID 40176

2 BR

2 ½ baths

Sleeps 6

Two Bedroom Condo unit in Tashmoo Wood

Distance to beach: 1.5 miles Lake Tashmoo Town Beach

Summer:
$2,800 - $3,000/wk

Off Season:
$2,700 - $3,000/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

Distance to beach: Private beach on property

5.017 reviews

Summer:
$3,350/wk

Off Season:
$2,512 - $3,350/wk

Vineyard Haven

ID 39810

3 BR

1 bath

Sleeps 5

Charming 3-Bedroom Home in a Peaceful Neighborhood – Perfect

Distance to beach: 2.2 mi to Tisbury Town Beach

2 reviews

Summer:
$550 - $700/night
$3,850 - $4,800/wk

Off Season:
$550/night
$3,850 - $4,100/wk

Vineyard Haven

ID 29565

2 BR

2 baths

Sleeps 5

Vineyard Charmer

Distance to beach: 1 mile Owen Park Beach

Summer:
$3,400 - $3,600/wk

Off Season:
$3,050 - $3,250/wk

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

Distance to beach: 10 min walk Owen Park Beach and Lake Tashmoo Beach, Tisbury Town Beach also close

5.010 reviews

Summer:
$2,400 - $2,700/wk

Off Season:
$2,000 - $2,500/wk
$1,850 - $2,000/mo

Vineyard Haven

ID 7436

2 BR

1 bath

Sleeps 4

Relax..You're on Island Time...A little piece of paradise..

Distance to beach: 1 mile Tisbury Town Beach and 1 mile Owen Park Beach

4.947 reviews

Summer:
$1,800 - $2,000/wk

Off Season:
$250 - $350/night
$1,600 - $1,800/wk
$1,700/mo

Vineyard Haven

ID 31287

2 BR

1 bath

Sleeps 4

Lovely Vineyard Condo - Walk To Ferry - Flexible Dates

Distance to beach: 7/10 mile to Owen Park Beach

5.03 reviews

Summer:
$2,200/wk

Off Season:
$1,200 - $2,200/wk

Vineyard Haven

ID 34386

2 BR

2 baths

Sleeps 4

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:
$3,750 - $5,500/wk

Off Season:
$425 - $650/night
$2,450 - $4,000/wk
$3,000 - $10,000/mo

West Chop

ID 35609

2 BR

1 bath

Sleeps 4

Cozy West Chop Hideaway

Distance to beach: 0.9 mi to Tisbury Town Beach

5.03 reviews

Summer:
$2,600 - $3,800/wk

Off Season:
$1,500 - $2,900/wk

VIneyard Haven

ID 36738

2 BR

1 bath

Sleeps 4

Charming Vineyard Haven Cottage ~ Walk to Beach, Town, Park

Distance to beach: 4/10 mi Tisbury Town Beach

Summer:
$4,600 - $5,600/wk
$14,000 - $19,500/mo

Off Season:
$3,000 - $4,900/wk
$3,000 - $9,000/mo

Tisbury

ID 38371

2 BR

1 bath

Sleeps 4

Peaceful Upgraded Condo Minutes from VH and Ferry/Pool

Distance to beach: 0.8 miles Owen Park Beach

5.03 reviews

Summer:
$2,000 - $3,500/wk
$8,000 - $10,000/mo

Off Season:
$1,800 - $3,000/wk
$4,000 - $7,500/mo

Vineyard Haven

ID 39641

2 BR

1 bath

Sleeps 4

Waterfront Beach House! Incredible Sunsets and Lake access.

Distance to beach: 0.1 mi to Lake Tashmoo Town Beach and Sandy Path from House Leads to Private Beach

Summer:
$5,500 - $6,750/wk

Off Season:
$3,850 - $5,750/wk

Vineyard Haven

ID 38039

2 BR

2 baths

Sleeps 4

Cozy West Chop Cottage, Walk or Bike to Beach & Woods, Town

Distance to beach: 4/10 Mi to Grove Avenue Beach;1 mi Owen Park Beach

5.01 review

Summer:
$450 - $650/night
$3,999 - $4,999/wk
$17,000 - $19,000/mo

Off Season:
$299 - $699/night
$2,100 - $4,999/wk
$7,000 - $14,000/mo

West Chop

ID 39912

2 BR

2 baths

Sleeps 4

Walk to Beach; Close to Town & Dining; Newly Renovated

Distance to beach: 0.5 mi to Owen Park Beach

Summer:
$4,000 - $6,500/wk
$20,000/mo

Off Season:
$3,500 - $5,000/wk
$14,000 - $15,000/mo

Vineyard Haven vacation rentals that sleep 2

Vineyard Haven

ID 7718

1 BR

1 bath

Sleeps 2

Waterview of Vineyard Sound, sleeps 2.

Distance to beach: 10 minute walk to Owen Little Way Beach.

5.03 reviews

Summer:
$1,500 - $1,700/wk

Off Season:
$1,500/wk

Vineyard Haven

ID 29576

1 BR

1 bath

Sleeps 2

Stand Alone Condo Walking distance to Town and Ferry

Distance to beach: 1 mile to Owen Park

OWNER SPECIAL:

ALL AUGUST DATES STILL AVAILABLE -MAX 2 PEOPLE!!!

Summer:
$2,800 - $3,000/wk

Off Season:
$300/wk

Vineyard Haven

ID 21680

1 BR

1 bath

Sleeps 2

CCC - Cute, Cozy Condo with Pool

Distance to beach: Owen Park Beach under 1/2 mile

4.45 reviews

Summer:
$1,000 - $1,125/wk

Off Season:
$1,000 - $1,125/wk