Vacation rentals in Chilmark, MA

49 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Chilmark, MA

The CAVU Mansion on Bellevue - Chilmark, MA

The CAVU Mansion on Bellevue

Holiday Home, Chilmark

The CAVU Mansion on Bellevue is a holiday home in Chilmark. 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 The CAVU Mansion on Bellevue

The CAVU Mansion on Bellevue is a holiday home in Chilmark. 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 internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,548.

From$712/night
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Private cottage nestled in center of the Vineyard - Chilmark, MA

Private cottage nestled in center of the Vineyard

Holiday Home, Chilmark

Private cottage nestled in center of the Vineyard is a holiday home in Chilmark, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Private cottage nestled in center of the Vineyard

Private cottage nestled in center of the Vineyard is a holiday home in Chilmark, 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 $2,788.

From$398/night
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Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio. - Chilmark, MA

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Apartment, Chilmark

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio. is a apartment in Chilmark, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio. is a apartment in Chilmark, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,258.

From$465/night
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Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard - Chilmark, MA

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard

Cottage, Chilmark

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard is a cottage in Chilmark, with room for a group and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard is a cottage in Chilmark, with room for a group and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: laundry service, non smoking, and shower.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,508.

From$501/night
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Browse Vacation Rentals with a Pool in Chilmark, MA

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

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds! - Chilmark, MA

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds!

Holiday Home, Chilmark

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds! is a holiday home in Chilmark, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds!

Car Ferry ticket for Aug 28 & Sept 4 weeks, late Summer escape with less crowds! is a holiday home in Chilmark, with pool 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,139.

From$734/night
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Great two house compound, inground pool, great privacy - Chilmark, MA

Great two house compound, inground pool, great privacy

Holiday Home, Chilmark

Great two house compound, inground pool, great privacy is a holiday home in Chilmark, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Great two house compound, inground pool, great privacy

Great two house compound, inground pool, great privacy is a holiday home in Chilmark, 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: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,063.

From$1,152/night
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Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! - Chilmark, MA

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!

Holiday Home, Chilmark

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! is a holiday home in Chilmark, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for…

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About Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!

Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!! is a holiday home in Chilmark, with pool access, easy beach access, and parking. 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $16,658.

From$2,380/night
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Beautiful Estate with salt water pool & pond with kayaks - Chilmark, MA

Beautiful Estate with salt water pool & pond with kayaks

Holiday Home, Chilmark

Beautiful Estate with salt water pool & pond with kayaks is a holiday home in Chilmark, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks is a holiday home in Chilmark, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $22,509.

From$3,216/night
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Best Chilmark, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Pristine with central air and outdoor shower - Chilmark, MA

Pristine with central air and outdoor shower

Holiday Home, Chilmark

Pristine with central air and outdoor shower is a holiday home in Chilmark, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Pristine with central air and outdoor shower

Pristine with central air and outdoor shower is a holiday home in Chilmark, 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: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,283.

From$612/night
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Charming Recently Renovated 3-Bedroom Retreat - Chilmark, MA

Charming Recently Renovated 3-Bedroom Retreat

Holiday Home, Chilmark

Charming Recently Renovated 3-Bedroom Retreat is a holiday home in Chilmark, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Charming Recently Renovated 3-Bedroom Retreat

Charming Recently Renovated 3-Bedroom Retreat is a holiday home in Chilmark, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,033.

From$719/night
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Stylish renovated apartment, 2 miles from town, private gardens & fire pit - Chilmark, MA

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

Apartment, Chilmark

Stylish renovated apartment, 2 miles from town, private gardens & fire pit is a apartment in Chilmark, with parking and kitchen access. This stay gives travelers a comfortable base for…

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

Stylish renovated apartment, 2 miles from town, private gardens & fire pit is a apartment in Chilmark, 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 cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,326.

From$761/night
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Luxury Home in Exclusive Aquinnah - Chilmark, MA

Luxury Home in Exclusive Aquinnah

Holiday Home, Chilmark

Luxury Home in Exclusive Aquinnah is a holiday home in Chilmark, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury Home in Exclusive Aquinnah

Luxury Home in Exclusive Aquinnah is a holiday home in Chilmark, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,338.

From$1,334/night
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Best Pet-Friendly Vacation Rentals in Chilmark, MA

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

Short Walk to Town - Nice Comfortable -Reasonable - Chilmark, MA

Short Walk to Town - Nice Comfortable -Reasonable

Condo, Chilmark

Short Walk to Town - Nice Comfortable -Reasonable is a condo in Chilmark, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Short Walk to Town - Nice Comfortable -Reasonable

Short Walk to Town - Nice Comfortable -Reasonable is a condo in Chilmark, 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 $4,799.

From$686/night
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Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available. - Chilmark, MA

Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available.

Holiday Home, Chilmark

Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available. is a holiday home in Chilmark, with pool access, kitchen access, and a quieter setting. This stay gives…

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About Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available.

Airy, Quiet Vacation Rental Home, assn. pool on MV. Car ferry tix available. is a holiday home in Chilmark, with pool access, kitchen access, and a quieter setting. 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 $5,875.

From$839/night
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West Tisbury Gem with Association Pool + Hiking Trails, Close to All - Chilmark, MA

West Tisbury Gem with Association Pool + Hiking Trails, Close to All

Holiday Home, Chilmark

West Tisbury Gem with Association Pool + Hiking Trails, Close to All is a holiday home in Chilmark, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About West Tisbury Gem with Association Pool + Hiking Trails, Close to All

West Tisbury Gem with Association Pool + Hiking Trails, Close to All is a holiday home in Chilmark, with pet-friendly space and 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,167.

From$881/night
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Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond - Chilmark, MA

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

Holiday Home, Chilmark

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond is a holiday home in Chilmark, with pet-friendly space, easy beach access, and parking. This stay gives…

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About Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond

Secluded retreat in Seven Gates Farm on 7 Acres, Private Beach, Tennis, Pond is a holiday home in Chilmark, with pet-friendly space, easy beach access, and parking. 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 $8,408.

From$1,201/night
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Best Chilmark, MA vacation rentals with a kitchen

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

Vineyard Haven Oasis! - Chilmark, MA

Vineyard Haven Oasis!

Holiday Home, Chilmark

Vineyard Haven Oasis! is a holiday home in Chilmark, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Vineyard Haven Oasis!

Vineyard Haven Oasis! is a holiday home in Chilmark, 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 $5,334.

From$762/night
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Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom - Chilmark, MA

Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom

Holiday Home, Chilmark

Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom is a holiday home in Chilmark, with kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom

Beautiful Estate with Large Lawn Made for Socializing and Kids' Playroom is a holiday home in Chilmark, 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 $6,098.

From$871/night
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New 5BR Luxury Home Near Ferry – Huge Deck, Fire Pit, Sleeps 12 - Chilmark, MA

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

Holiday Home, Chilmark

New 5BR Luxury Home Near Ferry – Huge Deck, Fire Pit, Sleeps 12 is a holiday home in Chilmark, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base…

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

New 5BR Luxury Home Near Ferry – Huge Deck, Fire Pit, Sleeps 12 is a holiday home in Chilmark, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,130.

From$1,019/night
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Edgartown Long Point Escape, Very Spacious Quite Private Location, Central A/C - Chilmark, MA

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

Holiday Home, Chilmark

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

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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 Chilmark, 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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Our Favorite Family-Friendly Vacation Rentals in Chilmark, MA

Plan a trip with stays that give families more room to spread out.

Vineyard Haven, Close to town and Lake Tashmoo - Chilmark, MA

Vineyard Haven, Close to town and Lake Tashmoo

Holiday Home, Chilmark

Vineyard Haven, Close to town and Lake Tashmoo is a holiday home in Chilmark, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Vineyard Haven, Close to town and Lake Tashmoo

Vineyard Haven, Close to town and Lake Tashmoo is a holiday home in Chilmark, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,203.

From$600/night
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Secluded Cottage, West Tisbury, Lambert's Cove Beach Access - Chilmark, MA

Secluded Cottage, West Tisbury, Lambert's Cove Beach Access

Holiday Home, Chilmark

Secluded Cottage, West Tisbury, Lambert's Cove Beach Access is a holiday home in Chilmark, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Secluded Cottage, West Tisbury, Lambert's Cove Beach Access

Secluded Cottage, West Tisbury, Lambert's Cove Beach Access is a holiday home in Chilmark, with 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: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,321.

From$760/night
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3BR House Close to Beach: Large Yard & Deck! - Chilmark, MA

3BR House Close to Beach: Large Yard & Deck!

Cottage, Chilmark

3BR House Close to Beach: Large Yard & Deck! is a cottage in Chilmark, with easy beach access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 3BR House Close to Beach: Large Yard & Deck!

3BR House Close to Beach: Large Yard & Deck! is a cottage in Chilmark, 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, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,683.

From$789/night
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Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis! - Chilmark, MA

Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

Holiday Home, Chilmark

Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis! is a holiday home in Chilmark, with easy beach access and kitchen access. This stay gives travelers a…

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About Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis! is a holiday home in Chilmark, with 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: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $8,979.

From$1,283/night
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