Gloucester, Massachusetts

Vacation Rentals in Gloucester, Massachusetts

Discover 203 vacation rental properties in Gloucester. From 1 to 8 bedrooms. Average $438/night. 100% have pools.

203 verified listings Book securely on VRBO Prices updated March 2026

203 properties available

A tranquil ocean retreat steps from the water's edge

A tranquil ocean retreat steps from the water's edge

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
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"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

1 bed 1 bath
PoolA/CWiFiBalcony
$163/night
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Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

4 beds 2 baths
PoolA/CWiFiBalcony
$429/night
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Luxury Accommodations in Quiet Seaside Village

Luxury Accommodations in Quiet Seaside Village

1 bed
PoolA/CWiFiBalcony
$180/night
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Prime Gloucester Property Overlooking Inner Harbor - CLOSING DECEMBER 15, 2024

Prime Gloucester Property Overlooking Inner Harbor - CLOSING DECEMBER 15, 2024

2 beds 2 baths
PoolA/CWiFiBalcony
$329/night
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Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

3 beds 1 bath
PoolA/CWiFiBalcony
$225/night
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Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

3 beds 1 bath
PoolA/CWiFiBalcony
Price on request
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Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!

2 beds 1 bath
PoolA/CWiFiBalcony
$243/night
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Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

2 beds 2 baths
PoolA/CWiFiBalcony
$366/night
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"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

1 bed 1 bath
PoolA/CWiFiBalcony
$193/night
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Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach

Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$140/night
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Good Harbor Beach Apt.- 6/10 mile walk

Good Harbor Beach Apt.- 6/10 mile walk

1 bed 1 bath
PoolA/CWiFiBalcony
$192/night
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Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks

Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks

1 bath
PoolA/CWiFiBalcony
$337/night
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4 Bedroom LUX House/with Pool Next Door

4 Bedroom LUX House/with Pool Next Door

4 beds 2 baths
PoolA/CWiFiBalcony
$351/night
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Single Level Home - Steps to Downtown Gloucester & A/C throughout

Single Level Home - Steps to Downtown Gloucester & A/C throughout

2 beds 1 bath
PoolA/CWiFiBalcony
$271/night
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Romantic Summerwind Cottage, Scenic Harbor View w/Spacious Deck!

Romantic Summerwind Cottage, Scenic Harbor View w/Spacious Deck!

2 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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Gloucester Studio - Om Suite Om~ near Good Harbor Beach

Gloucester Studio - Om Suite Om~ near Good Harbor Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$103/night
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La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!

La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!

1 bed 1 bath
PoolA/CWiFiBalcony
$161/night
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The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower

The Birdhouse • Woodland Retreat • Gloucester+Essex • Firepit • Outdoor shower

2 beds 2 baths
PoolA/CWiFiBalcony
$337/night
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Ocean and Woods! Best of both seaside delights in Gloucester!

Ocean and Woods! Best of both seaside delights in Gloucester!

2 beds 1 bath
PoolA/CWiFiBalcony
$191/night
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WALK TO BEACH! Conveniently located! Beautifully updated!

WALK TO BEACH! Conveniently located! Beautifully updated!

2 beds 1 bath
PoolA/CWiFiBalcony
$400/night
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Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Charming Retreat

Charming Retreat

2 beds 1 bath
PoolA/CWiFiBalcony
$249/night
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Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

1 bed 1 bath
PoolA/CWiFiBalcony
$305/night
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Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

3 beds 2 baths
PoolA/CWiFiBalcony
$375/night
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Sunset Cove: Waterfront home in Goose Cove section of Gloucester.

Sunset Cove: Waterfront home in Goose Cove section of Gloucester.

2 beds 2 baths
PoolA/CWiFiBalcony
$415/night
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Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront

Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront

3 beds 2 baths
PoolA/CWiFiBalcony
$315/night
View Details → Book on VRBO
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.

2 beds 1 bath
PoolA/CWiFiBalcony
$290/night
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Cozy 2 bedroom between the beach and downtown

Cozy 2 bedroom between the beach and downtown

2 beds 1 bath
PoolA/CWiFiBalcony
$185/night
View Details → Book on VRBO
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

3 beds 2 baths
PoolA/CWiFiBalcony
$386/night
View Details → Book on VRBO
Evensong: Oceanview Retreat with Dock

Evensong: Oceanview Retreat with Dock

3 beds 3 baths
PoolA/CWiFiBalcony
$541/night
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C by the Sea - Ocean View Penthouse

C by the Sea - Ocean View Penthouse

1 bed 1 bath
PoolA/CWiFiBalcony
$462/night
View Details → Book on VRBO
Walk to the ocean, very private. Secluded, woodsy location.

Walk to the ocean, very private. Secluded, woodsy location.

1 bed 1 bath
PoolA/CWiFiBalcony
$112/night
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Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!

1 bed 1 bath
PoolA/CWiFiBalcony
$244/night
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VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.

VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.

2 beds 1 bath
PoolA/CWiFiBalcony
$202/night
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River Watch: Waterfront home with river views and a private dock.

River Watch: Waterfront home with river views and a private dock.

3 beds 2 baths
PoolA/CWiFiBalcony
$410/night
View Details → Book on VRBO
2BR/2BA Harborside Home · Fenced Backyard · Ocean View ·Walk to Rocky Neck+Beach

2BR/2BA Harborside Home · Fenced Backyard · Ocean View ·Walk to Rocky Neck+Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$324/night
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Brand New Construction.....@Coffins Beach

Brand New Construction.....@Coffins Beach

2 beds 2 baths
PoolA/CWiFiBalcony
$441/night
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Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6

Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6

3 beds 2 baths
PoolA/CWiFiBalcony
$425/night
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Walk to Good Harbor Beach

Walk to Good Harbor Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
View Details → Book on VRBO
Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester

2 beds 1 bath
PoolA/CWiFiBalcony
$175/night
View Details → Book on VRBO
Massachusetts Abode w/ Deck & Grill: Near Beaches!

Massachusetts Abode w/ Deck & Grill: Near Beaches!

2 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
View Details → Book on VRBO
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

3 beds 1 bath
PoolA/CWiFiBalcony
$384/night
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Large, open floor plan. Water views of Lanes Cove. Walk to Plum Cove beach.

Large, open floor plan. Water views of Lanes Cove. Walk to Plum Cove beach.

1 bed 1 bath
PoolA/CWiFiBalcony
$204/night
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The Quarry

The Quarry

1 bed 1 bath
PoolA/CWiFiBalcony
$263/night
View Details → Book on VRBO
Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach

1 bed 1 bath
PoolA/CWiFiBalcony
$230/night
View Details → Book on VRBO
Salt Island Views: Walking distance to Good Harbor & Long Beach.

Salt Island Views: Walking distance to Good Harbor & Long Beach.

3 beds 2 baths
PoolA/CWiFiBalcony
$605/night
View Details → Book on VRBO

Showing 48 of 203 properties

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