Vacation rentals in Gloucester, MA

110 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Gloucester, MA

Harborside Oasis ★ Harbor View ★ Heart of Downtown - Gloucester, MA

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Apartment, Gloucester

Harborside Oasis ★ Harbor View ★ Heart of Downtown is a apartment in Gloucester, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown is a apartment in Gloucester, 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 wifi, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,649.

From$236/night
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Good Harbor Beach Apt.- 6/10 mile - Gloucester, MA

Good Harbor Beach Apt.- 6/10 mile

Apartment, Gloucester

Good Harbor Beach Apt.- 6/10 mile is a apartment in Gloucester, with pet-friendly space, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Good Harbor Beach Apt.- 6/10 mile

Good Harbor Beach Apt.- 6/10 mile is a apartment in Gloucester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,743.

From$249/night
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Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass - Gloucester, MA

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass

Holiday Home, Gloucester

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass is a holiday home in Gloucester, with easy beach access and room for a group. This stay gives travelers a…

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About Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass

Welcoming 1-bedroom in charming Annisquam section of Gloucesterwith beach pass is a holiday home in Gloucester, with easy beach 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$255/night
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Large 2 room studio with full kitchen and deck - Gloucester, MA

Large 2 room studio with full kitchen and deck

Apartment, Gloucester

Large 2 room studio with full kitchen and deck is a apartment in Gloucester, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for exploring…

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About Large 2 room studio with full kitchen and deck

Large 2 room studio with full kitchen and deck is a apartment in Gloucester, with pet-friendly space, outdoor space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,194.

From$313/night
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Best Gloucester, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Spy Glass - Views of Ipswich Bay - Gloucester, MA

Spy Glass - Views of Ipswich Bay

Holiday Home, Gloucester

Spy Glass - Views of Ipswich Bay is a holiday home in Gloucester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spy Glass - Views of Ipswich Bay

Spy Glass - Views of Ipswich Bay is a holiday home in Gloucester, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,496.

From$357/night
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Romantic Rockport Retreat with Scenic Coastal Views at The Crows Nest - Gloucester, MA

Romantic Rockport Retreat with Scenic Coastal Views at The Crows Nest

Apartment, Gloucester

Romantic Rockport Retreat with Scenic Coastal Views at The Crows Nest is a apartment in Gloucester, with parking and a quieter setting. This stay gives travelers a comfortable base for…

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About Romantic Rockport Retreat with Scenic Coastal Views at The Crows Nest

Romantic Rockport Retreat with Scenic Coastal Views at The Crows Nest is a apartment in Gloucester, with parking 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: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,507.

From$358/night
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The Orca – Modern Coastal Comfort Awaits - Gloucester, MA

The Orca – Modern Coastal Comfort Awaits

Apartment, Gloucester

The Orca – Modern Coastal Comfort Awaits is a apartment in Gloucester, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About The Orca – Modern Coastal Comfort Awaits

The Orca – Modern Coastal Comfort Awaits is a apartment in Gloucester, 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 $2,605.

From$372/night
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3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach - Gloucester, MA

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

Holiday Home, Gloucester

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach is a holiday home in Gloucester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About 3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach

3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach is a holiday home in Gloucester, 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 $2,958.

From$423/night
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Best Pet-Friendly Vacation Rentals in Gloucester, MA

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

Mill Lane: Enjoy all of Rockport's charms, right outside your door. - Gloucester, MA

Mill Lane: Enjoy all of Rockport's charms, right outside your door.

Holiday Home, Gloucester

Mill Lane: Enjoy all of Rockport's charms, right outside your door. is a holiday home in Gloucester, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base…

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About Mill Lane: Enjoy all of Rockport's charms, right outside your door.

Mill Lane: Enjoy all of Rockport's charms, right outside your door. is a holiday home in Gloucester, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,703.

From$386/night
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STUNNING OCEAN VIEWS FROM OUR COZY 2 BEDROOM COTTAGE! WEEKLY- SUNDAY TO SUNDAY - Gloucester, MA

STUNNING OCEAN VIEWS FROM OUR COZY 2 BEDROOM COTTAGE! WEEKLY- SUNDAY TO SUNDAY

Cottage, Gloucester

STUNNING OCEAN VIEWS FROM OUR COZY 2 BEDROOM COTTAGE! WEEKLY- SUNDAY TO SUNDAY is a cottage in Gloucester, with pet-friendly space, easy beach access, and kitchen access. This stay gives…

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About STUNNING OCEAN VIEWS FROM OUR COZY 2 BEDROOM COTTAGE! WEEKLY- SUNDAY TO SUNDAY

STUNNING OCEAN VIEWS FROM OUR COZY 2 BEDROOM COTTAGE! WEEKLY- SUNDAY TO SUNDAY is a cottage in Gloucester, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,770.

From$396/night
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Rockport Getaway Near Shops & Beaches - Gloucester, MA

Rockport Getaway Near Shops & Beaches

Holiday Home, Gloucester

Rockport Getaway Near Shops & Beaches is a holiday home in Gloucester, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Rockport Getaway Near Shops & Beaches

Rockport Getaway Near Shops & Beaches is a holiday home in Gloucester, 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: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,134.

From$448/night
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Twin Lights: Explore the village of Rockport! - Gloucester, MA

Twin Lights: Explore the village of Rockport!

Holiday Home, Gloucester

Twin Lights: Explore the village of Rockport! is a holiday home in Gloucester, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Twin Lights: Explore the village of Rockport!

Twin Lights: Explore the village of Rockport! is a holiday home in Gloucester, 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 $3,601.

From$514/night
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Best Gloucester, MA vacation rentals with a kitchen

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

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. - Gloucester, MA

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking.

Cottage, Gloucester

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. is a cottage in Gloucester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking.

Cozy 2BR ocean breeze cottage, AC, wifi, streaming tv, parking. is a cottage in Gloucester, 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 cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,785.

From$398/night
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Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! - Gloucester, MA

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants!

Apartment, Gloucester

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! is a apartment in Gloucester, with easy beach access, parking, and kitchen access. This stay gives travelers a…

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About Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants!

Bearskin Neck Rental in the Heart of Rockport! Walk to Beaches + Restaurants! is a apartment in Gloucester, 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 $3,006.

From$429/night
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Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor - Gloucester, MA

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor

Condo, Gloucester

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor is a condo in Gloucester, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor

Harborfront Pied a Terre Directly on Rockport’s Beautiful Old Harbor is a condo in Gloucester, 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 beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,200.

From$457/night
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5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! - Gloucester, MA

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!

Holiday Home, Gloucester

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! is a holiday home in Gloucester, with easy beach access and kitchen access. This stay gives travelers a comfortable base…

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About 5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade!

5 minute walk to Beach, Stage Fort Park, and Gloucester Promenade! is a holiday home in Gloucester, 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,647.

From$521/night
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Our Favorite Family-Friendly Vacation Rentals in Gloucester, MA

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

Private Cottage with AC & wifi, Steps to the Beach - Gloucester, MA

Private Cottage with AC & wifi, Steps to the Beach

Cottage, Gloucester

Private Cottage with AC & wifi, Steps to the Beach is a cottage in Gloucester, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Private Cottage with AC & wifi, Steps to the Beach

Private Cottage with AC & wifi, Steps to the Beach is a cottage in Gloucester, with 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, parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,684.

From$383/night
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2BR Home Minutes to Downtown Rockport+Beach! - Gloucester, MA

2BR Home Minutes to Downtown Rockport+Beach!

Cottage, Gloucester

2BR Home Minutes to Downtown Rockport+Beach! is a cottage in Gloucester, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 2BR Home Minutes to Downtown Rockport+Beach!

2BR Home Minutes to Downtown Rockport+Beach! is a cottage in Gloucester, 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 $2,721.

From$389/night
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~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun - Gloucester, MA

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun

Holiday Home, Gloucester

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun is a holiday home in Gloucester, with pet-friendly space, easy beach access, and kitchen access. This stay…

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About ~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun

~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun is a holiday home in Gloucester, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,429.

From$490/night
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Family Friendly Townhouse 75 steps from Long Beach - Gloucester, MA

Family Friendly Townhouse 75 steps from Long Beach

Holiday Home, Gloucester

Family Friendly Townhouse 75 steps from Long Beach is a holiday home in Gloucester, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Family Friendly Townhouse 75 steps from Long Beach

Family Friendly Townhouse 75 steps from Long Beach is a holiday home in Gloucester, with easy beach access, 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, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,706.

From$529/night
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