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Properties Available 672 properties available
BR1 Queen with Adjoining Bath, First FloorAdjoining Hall Bath with Shower Tub Combo, First FloorBR2 Queen with Adjoining Bath, First FloorOverflow: Trundle in Hallway
Edgartown Downtown 6
Edgartown Downtown 6 2
Edgartown Downtown 6 3
Edgartown Downtown 6 4
Edgartown Downtown 6 5
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$3,500.00 - $5,075.00 / per week + taxes and fees
Beds 2 beds
Baths 1 Full Bath
Sleeps sleeps 4
Edgartown Downtown 6
This sweet two bedroom Edgartown cottage is perfect for those that desire a bungalow with all the necessary amenities to complete their summer vacatio... Read More
June 2025
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BR1 King, First FloorHall Bath with Tub Shower Combo, First FloorBR2 (2) Twin Beds, First Floor
Vineyard Haven 929
Vineyard Haven 929 2
Vineyard Haven 929 3
Vineyard Haven 929 4
Vineyard Haven 929 5
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$4,900.00 - $5,900.00 / per week + taxes and fees
Beds 2 beds
Baths 1 Full Bath
Sleeps sleeps 4
Vineyard Haven 929
This gracious home, beautifully restored reflects a combination of original and new - with an abundance of outdoor space to run about! The woodwork e... Read More
June 2025
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1 2 3 4 5 6 $4,900 7
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July 2025
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    1 2 3 4 $4,900 5
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August 2025
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10 11 12 13 14 15 $5,900 16
17 18 19 20 21 22 $5,900 23
24 25 26 27 28 29 $4,900 30
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BR1 King En Suite with Separate Tub & Shower Stall, First FloorBR2 Queen, Second FloorBR3 (2) Twin Beds, Second FloorHall Bath with Tub Shower Combo, Second FloorPowder Room, First Floor
Edgartown 705
Edgartown 705 2
Edgartown 705 3
Edgartown 705 4
Edgartown 705 5
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$3,000.00 - $4,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 6
Edgartown 705
Edgartown vacation home offering great privacy, lots of light and open contemporary design. Spend days at the beach or wandering around town to visit... Read More
June 2025
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24 25 26 27 28 29 $3,900 30
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BR1 Queen, 1st floorHall bath with shower stall, 1st floorBR2 Queen en suite with shower stall, 2nd floor loft
Oak Bluffs Guest 8018
Oak Bluffs Guest 8018 2
Oak Bluffs Guest 8018 3
Oak Bluffs Guest 8018 4
Oak Bluffs Guest 8018 5
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$1,500.00 - $4,000.00 / per week + taxes and fees
Beds 2 beds
Baths 2 Full Bath
Sleeps sleeps 4
Oak Bluffs Guest 8018
Modern two-bedroom guest house, just moments from everything you want to do in Oak Bluffs. Classic post and beam design packs a lot of living space in... Read More
June 2025
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1 2 3 4 5 6 $3,000 7
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BR1 King with en suite, First FloorBR2 Queen, First FloorBR3 Queen, First FloorHall bath with tub/shower, First FloorOffice Space, First FloorTwin Trundle, Lower LevelBathroom with shower stall, Lower Level
Oak Bluffs 838
Oak Bluffs 838 2
Oak Bluffs 838 3
Oak Bluffs 838 4
Oak Bluffs 838 5
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$3,000.00 - $6,250.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full Bath
Sleeps sleeps 8
Oak Bluffs 838
This classic 3 bedroom Oak Bluffs home is perfect for relaxing, entertaining and spending quality time with family. All 3 of the bedrooms are on the M... Read More
June 2025
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1 2 3 4 5 6 $4,750 7
8 9 10 11 12 13 $4,750 14
15 16 17 18 19 20 $4,750 21
22 23 24 25 26 27 $6,000 28
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July 2025
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    1 2 3 4 $6,000 5
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BR1 Double Bedroom with 1/2 bath first floorBR2 King Bedroom second floor with full bathroom BR3 Queen Bedroom second floorBR4 (2)Twin beds second floor Full bathroom second floorStudio in separate building with twin trundle and queen sofa sleeper Mini Split units in bedrooms and dining room.
West Tisbury 1069
West Tisbury 1069 2
West Tisbury 1069 3
West Tisbury 1069 4
West Tisbury 1069 5
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$4,500.00 / per week + taxes and fees
Beds 5 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
West Tisbury 1069
A Summer Dream Come True! A vacation in the historic district of the first settlement on Martha's Vineyard! Plan to stay in our beautifully renovated ... Read More
June 2025
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1 2 3 4 5 6 $4,500 7
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15 16 17 18 19 20 $4,500 21
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BR1 King en suite with shower, 1st floor(BR1 step down into bedroom from hall)BR2 Queen, 2nd floorBR3 (2)Double beds, 2nd floorHall bath with tub/shower, 2nd floorHalf bath, 1st floorNote: Several steps up & down throughout main level
Oak Bluffs 860
Oak Bluffs 860 2
Oak Bluffs 860 3
Oak Bluffs 860 4
Oak Bluffs 860 5
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Pet Friendly
$4,000.00 - $7,000.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full, 1 Half Bath
Sleeps sleeps 8
Oak Bluffs 860
This comfortable three bedroom vacation home is centrally located on the bike path and approximately four miles from the townships and beautiful beach... Read More
June 2025
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BR1 Queen En Suite with Shower Stall, First FloorBR2 King, 2nd floorBR3 Queen, 2nd floorHall bath with tub and shower, 2nd floorBR4 (2) doubles, lower levelHall Bath with Shower Stall, Lower Level
Vineyard Haven 965
Vineyard Haven 965 2
Vineyard Haven 965 3
Vineyard Haven 965 4
Vineyard Haven 965 5
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$12,000.00 - $18,000.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 10
Vineyard Haven 965
Experience this modern and contemporary home nestled in a private setting off Lambert's Cove Road. Spread out on 3 levels, this home has modern amenit... Read More
June 2025
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1 2 3 4 5 6 $12,000 7
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    1 2 3 4 $16,000 5
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17 18 19 20 21 22 $18,000 23
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BR1: King, Television and Ensuite Bath. BR2: Pair of Twins with Twin Daybed, Television. Shared Hall Bath with BR3: Queen with Television, open staircase to first floor. All Bedrooms are on the Second Floor.
Vineyard Haven 1241
Vineyard Haven 1241 2
Vineyard Haven 1241 3
Vineyard Haven 1241 4
Vineyard Haven 1241 5
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$6,000.00 - $8,500.00 / per week + taxes and fees
Beds 3 beds
Baths 3 Full Bath
Sleeps sleeps 7
Vineyard Haven 1241
Follow the gentle stone pillars and then gently turn right into a lovely neighborhood, where the roads narrow a bit and the hustle and bustle fade awa... Read More
June 2025
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17 18 19 20 21 22 $7,000 23
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BR1 Queen, First FloorBR2 Queen, First FloorHall Bath with Shower Stall, First FloorBR3 Queen, Second FloorBR4 (2) Twin Beds, Second FloorHall Bath with Shower Stall, Second Floor
Oak Bluffs 8802
Oak Bluffs 8802 2
Oak Bluffs 8802 3
Oak Bluffs 8802 4
Oak Bluffs 8802 5
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$3,882.00 - $10,000.00 / per week + taxes and fees
Beds 4 beds
Baths 2 Full Bath
Sleeps sleeps 10
Oak Bluffs 8802
This beautifully renovated home, accommodating up to 10 guests, is located just minutes from Oak Bluffs, the vibrant hub of the harbor and village act... Read More
June 2025
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July 2025
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August 2025
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BR1 King En Suite with Shower Stall, Second FloorBR2 Queen, First FloorHall Bath with Shower Stall, First FloorBR3 (2) Twin Beds, First FloorLaundry, Lower Level
Edgartown Chappaquiddick 407
Edgartown Chappaquiddick 407 2
Edgartown Chappaquiddick 407 3
Edgartown Chappaquiddick 407 4
Edgartown Chappaquiddick 407 5
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$3,000.00 - $4,500.00 / per week + taxes and fees
Beds 3 beds
Baths 2 Full Bath
Sleeps sleeps 6
Edgartown Chappaquiddick 407
Three bedroom chappy cottage, open kitchen, dining, and living area. Two bedrooms on the first floor with access to a hall bathroom. A spacious king s... Read More
June 2025
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1 2 3 4 5 6 $3,500 7
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17 18 19 20 21 22 $4,500 23
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BR1 King En Suite with Tub Shower Combo, First FloorBR2 Queen, First FloorHall Bath with Shower Stall, First Floor BR3 Queen, Second FloorBR4 Bunk Bed & Twin, Second FloorHall Bath with Tub Shower Combo, Second FloorPowder Room, First Floor
Oak Bluffs 831
Oak Bluffs 831 2
Oak Bluffs 831 3
Oak Bluffs 831 4
Oak Bluffs 831 5
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$4,600.00 - $7,200.00 / per week + taxes and fees
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps sleeps 8
Oak Bluffs 831
Located in the serene Iron Hill Farm area just beyond the Islands' Alpaca Farm, this spacious four bedroom contemporary Cape offers large rooms, exten... Read More
June 2025
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1 2 3 4 5 6 $4,600 7
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July 2025
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6 7 8 9 10 11 $5,300 12
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