Vacation rentals in Chappaquiddick Island, MA

Best vacation rentals and Airbnb offers in Chappaquiddick Island, MA

Island Getaway

Holiday Home, Chappaquiddick Island

Island Getaway is a holiday home in Chappaquiddick Island. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Island Getaway

Island Getaway is a holiday home in Chappaquiddick Island. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: ac, air conditioning, heating, and garden.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,079.

From$362/night

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Chappy House, 1 mile from Edgartown Harbor

Holiday Home, Chappaquiddick Island

Chappy House, 1 mile from Edgartown Harbor is a holiday home in Chappaquiddick Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Chappy House, 1 mile from Edgartown Harbor

Chappy House, 1 mile from Edgartown Harbor is a holiday home in Chappaquiddick Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,907.

From$558/night

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Ideal Contemporary, Walk to Town, Central AC, 100% Renewable Energy

Holiday Home, Chappaquiddick Island

Ideal Contemporary, Walk to Town, Central AC, 100% Renewable Energy is a holiday home in Chappaquiddick Island, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Ideal Contemporary, Walk to Town, Central AC, 100% Renewable Energy

Ideal Contemporary, Walk to Town, Central AC, 100% Renewable Energy is a holiday home in Chappaquiddick Island, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,155.

From$594/night

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Bright and airy 4-bedroom house on Chappy near Wasque

Holiday Home, Chappaquiddick Island

Bright and airy 4-bedroom house on Chappy near Wasque is a holiday home in Chappaquiddick Island, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Bright and airy 4-bedroom house on Chappy near Wasque

Bright and airy 4-bedroom house on Chappy near Wasque is a holiday home in Chappaquiddick Island, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,226.

From$604/night

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Waterfront vacation rentals in Chappaquiddick Island, MA

Discover vacation rentals close to the coast, water, and beach areas around Chappaquiddick Island, MA.

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Holiday Home, Chappaquiddick Island

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs is a holiday home in Chappaquiddick Island, with easy beach access, outdoor space, and kitchen access. This stay…

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About Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs is a holiday home in Chappaquiddick Island, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,259.

From$466/night

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Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches

Holiday Home, Chappaquiddick Island

Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches is a holiday home in Chappaquiddick Island, with easy beach access, outdoor space, and kitchen access. This stay gives…

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About Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches

Charming Home with Deck, Screened Porch, Private Balcony, Near Beaches is a holiday home in Chappaquiddick Island, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,189.

From$884/night

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Beautiful Katama House between Edgartown and South Beach

Holiday Home, Chappaquiddick Island

Beautiful Katama House between Edgartown and South Beach is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Beautiful Katama House between Edgartown and South Beach

Beautiful Katama House between Edgartown and South Beach is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,516.

From$931/night

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Oceanviews, Walk to Beaches, Nature Preserves,

Holiday Home, Chappaquiddick Island

Oceanviews, Walk to Beaches, Nature Preserves, is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Oceanviews, Walk to Beaches, Nature Preserves,

Oceanviews, Walk to Beaches, Nature Preserves, is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,995.

From$999/night

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Vacation rentals with a pool in Chappaquiddick Island, MA

Add a pool to the search when you want an easy place to cool off between outings.

New King Bed, Studio -Downtown Edgartown

Condo, Chappaquiddick Island

New King Bed, Studio -Downtown Edgartown is a condo in Chappaquiddick Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About New King Bed, Studio -Downtown Edgartown

New King Bed, Studio -Downtown Edgartown is a condo in Chappaquiddick Island, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,918.

From$1,131/night

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Exquisite privacy and luxury just minutes from upscale Edgartown

Holiday Home, Chappaquiddick Island

Exquisite privacy and luxury just minutes from upscale Edgartown is a holiday home in Chappaquiddick Island, with pet-friendly space, pool access, and kitchen access. This stay gives…

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About Exquisite privacy and luxury just minutes from upscale Edgartown

Exquisite privacy and luxury just minutes from upscale Edgartown is a holiday home in Chappaquiddick Island, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,433.

From$1,348/night

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4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown.

Holiday Home, Chappaquiddick Island

4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown. is a holiday home in Chappaquiddick Island, with pool access. This stay gives travelers a comfortable base for exploring the…

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About 4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown.

4 BDR house with CUSTOM POOL, SPA and FIRE PIT in Edgartown. is a holiday home in Chappaquiddick Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,225.

From$1,746/night

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Beautiful 4 Bedroom House with Private Pool and Private Beach Access

Holiday Home, Chappaquiddick Island

Beautiful 4 Bedroom House with Private Pool and Private Beach Access is a holiday home in Chappaquiddick Island, with pool access, easy beach access, and kitchen access. This stay gives…

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About Beautiful 4 Bedroom House with Private Pool and Private Beach Access

Beautiful 4 Bedroom House with Private Pool and Private Beach Access is a holiday home in Chappaquiddick Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $12,754.

From$1,822/night

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Vacation rentals with parking in Chappaquiddick Island, MA

Find vacation rentals that make arriving by car easier.

Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking

Holiday Home, Chappaquiddick Island

Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking is a holiday home in Chappaquiddick Island, with outdoor space, parking, and kitchen access. This stay gives…

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About Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking

Bright Modern House AC 3full baths, 3+ bedrooms, 2 balconies, deck & parking is a holiday home in Chappaquiddick Island, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,768.

From$824/night

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#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

Holiday Home, Chappaquiddick Island

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay…

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About #CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach!

#CozyBluffs #OakBluffs #EastChop 1 BD, 1.5 bath home-Walk to Town-Ferries-Beach! is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,925.

From$846/night

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Beautiful 4 bedroom, air conditioned, within minutes of downtown Edgartown

Holiday Home, Chappaquiddick Island

Beautiful 4 bedroom, air conditioned, within minutes of downtown Edgartown is a holiday home in Chappaquiddick Island, with parking, kitchen access, and room for a group. This stay gives…

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About Beautiful 4 bedroom, air conditioned, within minutes of downtown Edgartown

Beautiful 4 bedroom, air conditioned, within minutes of downtown Edgartown is a holiday home in Chappaquiddick Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,370.

From$1,053/night

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Katama - Walk to Town & Beach!

Holiday Home, Chappaquiddick Island

Katama - Walk to Town & Beach! is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Katama - Walk to Town & Beach!

Katama - Walk to Town & Beach! is a holiday home in Chappaquiddick Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,414.

From$1,202/night

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Pet-friendly vacation rentals in Chappaquiddick Island, MA

Bring your pet along with stays that welcome four-legged travelers.

Private setting nestled in the heart of East Chop.

Holiday Home, Chappaquiddick Island

Private setting nestled in the heart of East Chop. is a holiday home in Chappaquiddick Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Private setting nestled in the heart of East Chop.

Private setting nestled in the heart of East Chop. is a holiday home in Chappaquiddick Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,160.

From$737/night

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0.8 miles to Circuit Avenue in Downtown Oak Bluffs

Holiday Home, Chappaquiddick Island

0.8 miles to Circuit Avenue in Downtown Oak Bluffs is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About 0.8 miles to Circuit Avenue in Downtown Oak Bluffs

0.8 miles to Circuit Avenue in Downtown Oak Bluffs is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,579.

From$797/night

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Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C

Holiday Home, Chappaquiddick Island

Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C is a holiday home in Chappaquiddick Island, with kitchen access. This stay gives travelers a comfortable base…

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About Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C

Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C is a holiday home in Chappaquiddick Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,322.

From$1,046/night

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Pristine Chappy! Early July Late August 2026 Prime Weeks Available !

Holiday Home, Chappaquiddick Island

Pristine Chappy! Early July Late August 2026 Prime Weeks Available ! is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Pristine Chappy! Early July Late August 2026 Prime Weeks Available !

Pristine Chappy! Early July Late August 2026 Prime Weeks Available ! is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,737.

From$1,105/night

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Vacation rentals with a kitchen in Chappaquiddick Island, MA

Compare stays with kitchen access for longer trips and easier meals.

Private suite with roof deck, near golf, bus stop, shops, and trails

Apartment, Chappaquiddick Island

Private suite with roof deck, near golf, bus stop, shops, and trails is a apartment in Chappaquiddick Island, with outdoor space and kitchen access. This stay gives travelers a comfortable…

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About Private suite with roof deck, near golf, bus stop, shops, and trails

Private suite with roof deck, near golf, bus stop, shops, and trails is a apartment in Chappaquiddick Island, with outdoor space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,554.

From$508/night

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Quaint, ranch style home in Oak Bluffs with central air

Holiday Home, Chappaquiddick Island

Quaint, ranch style home in Oak Bluffs with central air is a holiday home in Chappaquiddick Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Quaint, ranch style home in Oak Bluffs with central air

Quaint, ranch style home in Oak Bluffs with central air is a holiday home in Chappaquiddick Island, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,803.

From$543/night

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Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown

Holiday Home, Chappaquiddick Island

Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown

Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown is a holiday home in Chappaquiddick Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,810.

From$1,401/night

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Gorgeous Edgartown 5 bedroom and Walk to Town

Holiday Home, Chappaquiddick Island

Gorgeous Edgartown 5 bedroom and Walk to Town is a holiday home in Chappaquiddick Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Gorgeous Edgartown 5 bedroom and Walk to Town

Gorgeous Edgartown 5 bedroom and Walk to Town is a holiday home in Chappaquiddick Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,810.

From$1,401/night

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