Top Winter Vacations - Vacation Rentals in Island Cove Adventures

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From US $295

         

|

9.6 (1 Review)

House

Islander's Retreat

• Air Conditioner
• Parking
• Balcony/Terrace

• Massachusetts
• Vineyard Haven

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From US $1,277

         

10.0 (71 Reviews)

House

Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!

• Air Conditioner
• Parking
• TV

• Oak Bluffs
• East Chop

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From US $265

         

9.8 (94 Reviews)

Hotel

The Attleboro House

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Massachusetts
• Oak Bluffs

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From US $702

         

|

8.0 (1 Review)

House

Treeside Lodge

• Air Conditioner
• Parking
• Pet Friendly

• Oak Bluffs
• East Chop

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From US $539

         

9.8 (52 Reviews)

House

Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Vineyard Haven

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From US $208

         

|

9.4 (1002 Reviews)

Hotel

Mansion House Inn And Spa

• Air Conditioner
• Pool
• TV

• Massachusetts
• Vineyard Haven

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From US $1,520

         

|

New

Villa

** Vineyard Vacation Retreat ** with NEW HOT TUB

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Oak Bluffs

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From US $541

         

9.8 (54 Reviews)

House

Cozy, Clean, Bikes, Kayaks, Laundry, Ferry Tickets, Near Bike Path and Town

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Oak Bluffs

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From US $446

         

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9.4 (63 Reviews)

Hotel

Lamberts Cove Inn

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Vineyard Haven

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From US $834

         

9.4 (32 Reviews)

House

Great Martha's Vineyard House: Everything You Need - Nothing You Don't!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Oak Bluffs

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From US $385

         

9.8 (24 Reviews)

House

Beautiful 3 bedroom 2 bath Home/Close to Town & Beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Oak Bluffs

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From US $378

         

9.4 (75 Reviews)

House

New Construction with Patio & Yard - Downtown & Beaches

• Air Conditioner
• Parking
• TV

• Massachusetts
• Oak Bluffs

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From US $531

         

9.6 (36 Reviews)

House

West Tisbury Country Home

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Vineyard Haven

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From US $1,692

         

9.4 (13 Reviews)

House

Relax & Renew at Luxury Villa with Heated Pool & Hot Tub,Tennis,Bikes,Firepit!

• Air Conditioner
• Parking
• Pool

• Oak Bluffs
• Lagoon Heights

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From US $407

         

9.4 (19 Reviews)

House

Conveniently located near Town

• Air Conditioner
• Parking
• TV

• Oak Bluffs
• East Chop

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From US $1,012

         

9.6 (44 Reviews)

House

Luxury Loft Historic Center Oak Bluffs

• Air Conditioner
• Parking
• TV

• Massachusetts
• Oak Bluffs

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From US $1,077

         

10.0 (8 Reviews)

House

Secluded Escape- Central AC & Wireless Internet Access.

• Air Conditioner
• Parking
• TV

• Oak Bluffs
• Lagoon Heights

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From US $814

         

9.6 (8 Reviews)

House

Beautiful Waterfront Home on Lake Tashmoo

• Air Conditioner
• Parking
• TV

• Vineyard Haven
• Tisbury

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From US $461

         

10.0 (75 Reviews)

House

Sparkling Waterfront Gem, Spectacular Views, Private Beach, Great for Kayaks

• Parking
• TV
• View

• Vineyard Haven
• Tisbury

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From US $1,053

         

10.0 (67 Reviews)

House

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Vineyard Haven

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From US $455

         

10.0 (62 Reviews)

House

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

• Parking
• TV
• View

• Massachusetts
• Vineyard Haven

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From US $334

         

10.0 (55 Reviews)

Cottage

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Vineyard Haven

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From US $549

         

10.0 (53 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Massachusetts
• Vineyard Haven

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From US $470

         

10.0 (48 Reviews)

Cottage

WATERFRONT Downtown Cottage w/Beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Vineyard Haven

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