Vineyard Haven Vacation Rentals

Vineyard Haven vacation rentals that sleep 18

Historic Captain's House/Sleeps 18/Walk to Ferry & Beaches
Vineyard Haven
ID 37866
  • 9 BR
  • 6 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

Summer:

$18,600 - $25,600/wk

Off Season:

$1,000 - $3,000/night

$6,600 - $18,600/wk

4

Vineyard Haven vacation rentals that sleep 14

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

$14,350/wk

Off Season:

$1,200 - $2,000/night

$5,850 - $9,950/wk

$24,500 - $27,000/mo

4

Vineyard Haven vacation rentals that sleep 12

Luxurious Six-Bedroom Vineyard Haven Cottage/Walk to Beach
Vineyard Haven
ID 39172
  • 6 BR
  • 4 baths
  • Sleeps 12

Luxurious Six-Bedroom Vineyard Haven Cottage/Walk to Beach

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

Summer:

$14,500 - $17,500/wk

Off Season:

$5,500 - $13,500/wk

10
Luxurious Beachfront Haven w/ Private Dock & Views
Vineyard Haven
ID 38942
  • 5 BR
  • 6 baths
  • Sleeps 12

Luxurious Beachfront Haven w/ Private Dock & Views

Distance to beach: Situated on Private Beach

Summer:

$16,000 - $36,000/wk

Off Season:

$1,800 - $2,700/night

$10,500 - $21,000/wk

4
Legacy House: Elegant 5BR Colonial w/ AC, Fire Pit, Privacy
Vineyard Haven
ID 41170
  • 5 BR
  • 3 baths
  • Sleeps 12

Legacy House: Elegant 5BR Colonial w/ AC, Fire Pit, Privacy

Distance to beach: 1.1 mi to Tisbury Town Beach
5.05 reviews

Summer:

$6,550 - $12,550/wk

Off Season:

$360 - $500/night

$3,550 - $8,550/wk

3
Hydrangea House
Hydrangea House
ID 41396
  • 5 BR
  • 2 baths
  • Sleeps 12

Hydrangea House

Distance to beach: 0.8 mi to Tisbury Town Beach

Summer:

$10,650 - $17,150/wk

Off Season:

$8,650 - $10,650/wk

*NEW LISTING* Vineyard Haven Home - Pet Friendly!
Vineyard Haven
ID 41638
  • 5 BR
  • 2 baths
  • Sleeps 12

*NEW LISTING* Vineyard Haven Home - Pet Friendly!

Distance to beach: 1.3 mi to Owen Park Beach and 0.1 mile to Tashmoo Pond (harbor)
5.02 reviews

Summer:

$880 - $1,000/night

$6,560/wk

Off Season:

$350 - $660/night

$2,400 - $5,200/wk

Vineyard Haven vacation rentals that sleep 11

Spacious 6BR Retreat – Walk to Town & Lagoon, Sleeps 11
Vineyard Haven
ID 40704
  • 6 BR
  • 2 baths
  • Sleeps 11

Spacious 6BR Retreat – Walk to Town & Lagoon, Sleeps 11

Distance to beach: 1.6 mi to Tisbury Town Beach

Summer:

$8,400 - $15,400/wk

Off Season:

$2,900 - $12,400/wk

$10,000/mo

3

Vineyard Haven vacation rentals that sleep 10

Vineyard Haven (in town), Recently Renovated, Harbor views
Vineyard Haven
ID 16690
  • 5 BR
  • 2 baths
  • Sleeps 10

Vineyard Haven (in town), Recently Renovated, Harbor views

Distance to beach: 1 block to Owen Park Beach
5.012 reviews

Off Season:

$6,250/wk

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

Summer:

$5,070/wk

Off Season:

$5,070/wk

5
4-Bedroom Vineyard Haven Home
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
4.920 reviews

Summer:

$6,450 - $7,950/wk

Off Season:

$500 - $700/night

$2,950 - $6,450/wk

3
Where Luxe, Comfort & Charm Merge;Beach,Tennis & Pool Access
Vineyard Haven
ID 40653
  • 4 BR
  • 3 baths
  • Sleeps 10

Where Luxe, Comfort & Charm Merge;Beach,Tennis & Pool Access

Distance to beach: 1.5 mi to Lake Tashmoo Town Beach and 4.1 mi to Tisbury Town Beach
OWNER SPECIAL:

Two consecutive week special! Rent two consecutive weeks between 7/11/27 and 8/1/27 for $500.00 off.

Summer:

$9,900 - $10,400/wk

Off Season:

$800 - $900/night

$6,400 - $8,900/wk

$18,900 - $20,000/mo

3

Vineyard Haven vacation rentals that sleep 9

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

$16,850 - $22,850/wk

Off Season:

$1,428/night

$7,850 - $17,850/wk

2

Vineyard Haven vacation rentals that sleep 8

Newly Renovated West Chop/Walk to Beach, Golf, and Ferry
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
5.010 reviews
OWNER SPECIAL:

Booking for Summer 2027! Cheaper rates for June and September. Take advantage of the peace and quiet

Summer:

$4,360 - $7,360/wk

Off Season:

$2,360 - $4,360/wk

4
Makonikey with Private Beach Nearby
Vineyard Haven
ID 37328
  • 4 BR
  • 2 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:

$6,350 - $7,850/wk

Off Season:

$4,350/wk

6
Captain Spring House: In-town Luxury with Water Views
Martha's Vineyard
ID 28424
  • 4 BR
  • 4 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:

$10,950/wk

Off Season:

$750 - $1,000/night

$5,700 - $8,440/wk

4
A/C Home w/ Peaceful Pool
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

Off Season:

$6,300/wk

Pool, Walk to Town or Tashmoo.
Tisbury
ID 41250
  • 4 BR
  • 2 baths
  • Sleeps 8

Pool, Walk to Town or Tashmoo.

Distance to beach: 1.3 mi to Tisbury Town Beach

Summer:

$7,350/wk

Off Season:

$7,350/wk

4
Vineyard Haven Gem - A perfect back drop for making memories
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
5.011 reviews

Summer:

$6,025 - $16,320/wk

Off Season:

$786 - $1,600/night

$6,025 - $10,320/wk

4

Vineyard Haven vacation rentals that sleep 7

Discounted Fall Rates - A/C - Walk to Town/Beach/Ferry
Vineyard Haven
ID 29593
  • 4 BR
  • 2 baths
  • Sleeps 7

Discounted Fall Rates - 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:

$4,600 - $6,000/wk

Off Season:

$3,500 - $4,600/wk

5
Vineyard Retreat |Winter Rental + 2 Prime Aug Weeks + Pool
Vineyard Haven
ID 42109
  • 4 BR
  • 2 baths
  • Sleeps 7

Vineyard Retreat |Winter Rental + 2 Prime Aug Weeks + Pool

Distance to beach: 0.4 mi to Tisbury Town Beach
5.01 review
OWNER SPECIAL:

No Lodging Tax! Winter Rental + 2 Prime August Weeks.

Summer:

$2,400 - $14,900/wk

Off Season:

$2,400/wk

$6,000 - $7,500/mo

4
Mitchell Manor By The Sea - Walk to Beach
Mitchell Manor By The Sea
ID 35701
  • 3 BR
  • 2 baths
  • Sleeps 7

Mitchell Manor By The Sea - Walk to Beach

Distance to beach: 1/2 mi to Tisbury Town Beach

Summer:

$4,500 - $8,000/wk

Off Season:

$529 - $643/night

$3,900 - $4,500/wk

4
Island Living New Bi Level Apartment
Vineyard Haven
ID 41372
  • 3 BR
  • 3 baths
  • Sleeps 7

Island Living New Bi Level Apartment

Distance to beach: 1.2 mi Tisbury Town Beach

Summer:

$7,350 - $16,850/wk

Off Season:

$2,550 - $8,850/wk

$3,500 - $7,000/mo

4

Vineyard Haven vacation rentals that sleep 6

Charming Cottage near West Chop- Vineyard Haven
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:

$3,770 - $3,970/wk

Off Season:

$536/night

$3,220 - $3,770/wk

$5,000/mo

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

$5,275 - $6,775/wk

Off Season:

$369 - $659/night

$2,875 - $5,275/wk

5
Commanding Lagoon Waterfront, Private Beach: 180° View
Vineyard Haven
ID 33283
  • 3 BR
  • 1 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:

$10,695 - $13,645/wk

Off Season:

$5,645 - $10,495/wk

$33,500/mo

7
Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!
Vineyard Haven
ID 27296
  • 3 BR
  • 1 bath
  • Sleeps 6

Charming 3 Bedroom Home Close to Downtown & Lake Tashmoo!

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

Summer:

$3,450 - $3,650/wk

Off Season:

$3,250 - $3,450/wk

3
Waterfront Classic w/Private Beach.Kayaks & Paddle Boards
Vineyard Haven
ID 37747
  • 3 BR
  • 2 baths
  • Sleeps 6

Waterfront Classic w/Private Beach.Kayaks & Paddle Boards

Distance to beach: 5 miles small waves. kid friendly State Beach and 7 miles. Large Waves. Strong under tow and tides South Beach - Katama
5.05 reviews

Summer:

$9,900/wk

10
Sunny Vineyard  Getaway Close to Everything steps from sound
Vineyard Haven
ID 37838
  • 3 BR
  • 2 baths
  • Sleeps 6

Sunny Vineyard Getaway Close to Everything steps from sound

Distance to beach: 8/10 mile to Tisbury Town Beach and 2.2 Lake Tashmoo Town Beach
5.06 reviews

Summer:

$4,300 - $5,100/wk

Off Season:

$3,800 - $4,300/wk

4
Vineyard Haven Townhouse with Pool
Vineyard Haven
ID 37831
  • 3 BR
  • 3 baths
  • Sleeps 6

Vineyard Haven Townhouse with Pool

Distance to beach: 1.0 mi to Lake Tashmoo Town Beach

Summer:

$3,850 - $4,450/wk

Off Season:

$392 - $478/night

$3,075 - $3,850/wk

Vineyard Getaway: Access to Pool, Dock, Trails, & Beaches!
Vineyard Haven
ID 33882
  • 3 BR
  • 3 baths
  • Sleeps 6

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
5.02 reviews

Off Season:

$3,400 - $5,350/wk

2
Hine's Point Waterfront
Vineyard Haven
ID 4482
  • 2 BR
  • 1 bath
  • Sleeps 6

Hine's Point Waterfront

Distance to beach: 1/2 mile
5.01 review

Summer:

$5,200 - $5,800/wk

Off Season:

$3,000 - $4,200/wk

Vineyard Haven vacation rentals that sleep 5

Warm & Cozy Three Bedroom Bungalow
Vineyard Haven
ID 40456
  • 3 BR
  • 1 bath
  • Sleeps 5

Warm & Cozy Three Bedroom Bungalow

Distance to beach: 1.0 mi to Tisbury Town Beach
5.01 review

Summer:

$900 - $950/night

$4,350 - $4,650/wk

$15,900 - $21,500/mo

Off Season:

$800 - $850/night

$1,050 - $4,150/wk

$2,600 - $12,100/mo

Vineyard Charmer
Vineyard Haven
ID 29565
  • 2 BR
  • 2 baths
  • Sleeps 5

Vineyard Charmer

Distance to beach: 1 mile Owen Park Beach
2

Vineyard Haven vacation rentals that sleep 4

Charming Bright Sunny Cape Home in Vineyard Haven
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:

$3,365/wk

Off Season:

$400 - $450/night

$2,465 - $3,265/wk

$1,900 - $2,450/mo

4
Charming Vineyard Haven Cottage ~ Walk to Beach, Town, Park
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:

$5,400 - $6,400/wk

$18,000 - $19,000/mo

Off Season:

$3,400 - $5,400/wk

$3,500/mo

6
Waterfront Beach House! Incredible Sunsets and Lake access.
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
5.01 review

Summer:

$6,700 - $7,800/wk

Off Season:

$4,200 - $6,160/wk

1
Architect Designed Two Bedroom Refuge w/Shared Private Beach
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:

$4,600 - $5,900/wk

$21,000/mo

Off Season:

$2,600 - $25,400/wk

$2,600 - $15,000/mo

4
Cozy West Chop Hideaway- Fall Availability!
West Chop
ID 35609
  • 2 BR
  • 1 bath
  • Sleeps 4

Cozy West Chop Hideaway- Fall Availability!

Distance to beach: 0.9 mi to Tisbury Town Beach
5.03 reviews

Off Season:

$1,750 - $2,750/wk

5
Peaceful Upgraded Condo walk to VH w AC, deck, pool
Tisbury
ID 38371
  • 2 BR
  • 1 bath
  • Sleeps 4

Peaceful Upgraded Condo walk to VH w AC, deck, pool

Distance to beach: 0.8 miles Owen Park Beach
5.04 reviews

Off Season:

$2,000 - $2,400/wk

$4,000 - $8,000/mo

3

Vineyard Haven vacation rentals that sleep 3

Blue Whale Cottages
Vineyard Haven
ID 41837
  • 1 BR
  • 1 bath
  • Sleeps 3

Blue Whale Cottages

Distance to beach: 1.2 mi to Tisbury Town Beach and 1.5 Eastville Beach

Summer:

$5,000 - $6,509/wk

Off Season:

$479 - $650/night

$1,500 - $5,000/wk

$2,500 - $3,000/mo

4

Vineyard Haven vacation rentals that sleep 2

Waterview of Vineyard Sound, sleeps 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:

$1,950/wk

Off Season:

$1,800 - $1,950/wk

$1,700/mo

CCC - Cute, Cozy Condo with Pool
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
4.56 reviews

Summer:

$1,025 - $1,150/wk

Off Season:

$1,025/wk