Vacation Rentals By Owner In Vineyard Haven, MA

Showing 80 Of 276 Vacation Rentals

$567.9

/ Nightly

Apartment

Spacious Second FL 4-Bedroom Rental – Private Entrance & Newly Renovated Deck!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(12)

Select Dates for Price

Private Vacation Home

New Waterfront Home, Secluded on Private Road w Pvt Beach, only 10min to town

West Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$728.92

/ Nightly

Private Vacation Home

New 2 min from Circuit ave

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$446.8

/ Nightly

Private Vacation Home

The Pearl: Lovely cottage, close to Vineyard Haven town/ferry

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(4)

$1037.57

/ Nightly

Private Vacation Home

Greek Revival-Inspired In-Town Luxury Getaway

Vineyard Haven, Massachusetts, United States

Bed

Bath

Sleeps

$754.45

/ Nightly

Private Vacation Home

Special offer 2026 Aug 28 & Sept 4 weeks take 10% off !

West Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$702.04

/ Nightly

Condo

Short Walk to Town - Nice Comfortable -Reasonable

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(32)

$781.34

/ Nightly

Private Vacation Home

Entire house walking distance from ferry

Vinyard Haven, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(15)

$531.69

/ Nightly

Private Vacation Home

Fully Renovated & Spacious home within walking distance of Oak Bluffs / Beaches

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$1367.21

/ Nightly

Private Vacation Home

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(30)

$1021.1

/ Nightly

Cottage

Beautiful Carriage House on the Chop

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(6)

$866.24

/ Nightly

Apartment

Stylish renovated apartment, 2 miles from town, private gardens & fire pit

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(1)

$1217.82

/ Nightly

Private Vacation Home

Historic Oak Bluffs Cottage – Porch with View

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(50)

$595.36

/ Nightly

Private Vacation Home

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(48)

$551.04

/ Nightly

Chalet

Gorgeous Chalet - Incredible Views - Hot Tub - Fire Pit

Snowshoe, West Virginia, United States

Bed

Bath

Sleeps

$891.93

/ Nightly

Private Vacation Home

4-bedroom house in Tisbury for a relaxing getaway - newly renovated

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(26)

$701.64

/ Nightly

Private Vacation Home

Beautiful home with pool in great location- close to everything!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(33)

$438.24

/ Nightly

Private Vacation Home

IN-TOWN-WALK TO EVERYTHING! Adorable & Affordable! A/C units in each bedroom!

Vineyard Haven, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(20)

$877.13

/ Nightly

Private Vacation Home

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$797.54

/ Nightly

Private Vacation Home

Charming Recently Renovated 3-Bedroom Retreat

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Rent a place that suits your needs

Private vacation home

View 227 Private vacation home

Most popular vacation rentals in Vineyard Haven

Exceptional(9)

$701.48

/ Nightly

Private vacation home

Close to town, beautifully updated

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$733.55

/ Nightly

Private vacation home

Charming West Chop Retreat on Private, Tree-Lined Lot

Vineyard Haven, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$733.50

/ Nightly

Private vacation home

New 5BR Luxury Home Near Ferry – Huge Deck, Fire Pit, Sleeps 12

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$728.92

/ Nightly

Private vacation home

New 2 min from Circuit ave

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$713.21

/ Nightly

Private vacation home

Downtown brand new construction 3 bed & 3 bath

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$702.04

/ Nightly

Condo

Short Walk to Town - Nice Comfortable -Reasonable

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$701.85

/ Nightly

Private vacation home

Oak Bluffs Family Retreat - Private Roundabout, Walk to the Beach & Downtown OB.

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$701.76

/ Nightly

Cottage

Cozy New TimberFrame Vineyard Haven!

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$701.64

/ Nightly

Private vacation home

Beautiful home with pool in great location- close to everything!

Oak Bluffs, Massachusetts, United States

Bed

Bath

Sleeps

Exceptional(9)

$665.73

/ Nightly

Private vacation home

Newly built house, Central A/C, Walk to ferry, beach, and town

Tisbury, Massachusetts, United States

Bed

Bath

Sleeps

Vacation Rentals By Owner In Vineyard Haven, MA

$567.9

$728.92

$446.8

$1037.57

$754.45

$702.04

$781.34

$531.69

$1367.21

$1021.1

$866.24

$1217.82

$595.36

$551.04

$891.93

$701.64

$438.24

$877.13

$797.54

Rent a place that suits your needs

Most popular vacation rentals in Vineyard Haven

$701.48

$733.55

$733.50

$728.92

$713.21

$702.04

$701.85

$701.76

$701.64

$665.73

Most Popular Cities in Massachusetts