Gloucester Vacation Rentals - Gloucester, Massachusetts Vacation Rental Deals on Lake Rentals, Beach Houses, Condos, Cabins, Villas by VacaGuru.com!

$Charming Gloucester Escape w\/ Private Garden!$

Charming Gloucester Escape w\/ Private Garden!

3
1.0
4

Gloucester Massachusetts Private vacation home Click For Pricing

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

1
1.0
2

Gloucester Massachusetts Apartment From $159 per night (USD)

Walk to Good Harbor Beach and Downtown Gloucester

Walk to Good Harbor Beach and Downtown Gloucester

1
1.0
2

Gloucester Massachusetts Apartment Click For Pricing

A tranquil ocean retreat steps from the water's edge

A tranquil ocean retreat steps from the water's edge

1
1.0
3

Gloucester Massachusetts Apartment From $200 per night (USD)

Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!

Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!

3
1.0
5

Gloucester Massachusetts Private vacation home From $401 per night (USD)

Stanwood Point: Waterfront cottage with dock, large screened porch, and yard

Stanwood Point: Waterfront cottage with dock, large screened porch, and yard

3
2.0
6

Gloucester Massachusetts Private vacation home Click For Pricing

Lovely 'Blue Heron Cottage' on Annisquam River!

Lovely 'Blue Heron Cottage' on Annisquam River!

3
1.0
6

Gloucester Massachusetts Cottage From $331 per night (USD)

Elegant Gloucester Beach Getaway with Ocean Views!

Elegant Gloucester Beach Getaway with Ocean Views!

5
2.0
11

Gloucester Massachusetts Private vacation home From $812 per night (USD)

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
2.0
6

Gloucester Massachusetts Private vacation home From $425 per night (USD)

Seaside Escape just steps to Good Harbor beach in Gloucester

Seaside Escape just steps to Good Harbor beach in Gloucester

2
1.0
5

Gloucester Massachusetts Private vacation home From $325 per night (USD)

♥ 2 Bedroom+Office|Minutes to Good Harbor+Rockport|Fast Wifi|Off-Street Parking♥

♥ 2 Bedroom+Office|Minutes to Good Harbor+Rockport|Fast Wifi|Off-Street Parking♥

2
1.0
6

Gloucester Massachusetts Apartment From $316 per night (USD)

WALK TO BEACH! Conveniently located! Beautifully updated!

WALK TO BEACH! Conveniently located! Beautifully updated!

2
3.0
6

Gloucester Massachusetts Cottage From $288 per night (USD)

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

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

2
1.0
4

Gloucester Massachusetts Private vacation home From $188 per night (USD)

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

3
1.0
6

Gloucester Massachusetts Apartment From $279 per night (USD)

$Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away$

Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away

4
5.0
8

Gloucester Massachusetts Private vacation home From $733 per night (USD)

COME STAY AT THE MERMAID COTTAGE ON LANES COVE !

COME STAY AT THE MERMAID COTTAGE ON LANES COVE !

1
1.0
3

Gloucester Massachusetts Private vacation home Click For Pricing

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

4
2.0
8

Gloucester Massachusetts Private vacation home From $270 per night (USD)

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

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

2
1.0
5

Gloucester Massachusetts Private vacation home From $287 per night (USD)

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

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

1
1.0
3

Gloucester Massachusetts Apartment From $203 per night (USD)

A walk up to heaven!

A walk up to heaven!

2
1.0
5

Gloucester Massachusetts Private vacation home Click For Pricing

Harbor Views, Perfect Downtown Location

Harbor Views, Perfect Downtown Location

2
2.0
6

Gloucester Massachusetts Condo From $646 per night (USD)

Beautiful 3 bed home...steps from Good Harbor and Long Beach!

Beautiful 3 bed home...steps from Good Harbor and Long Beach!

3
2.0
8

Gloucester Massachusetts Private vacation home From $525 per night (USD)

Quaint Home, Near Good Harbor Beach and Town, Great for Families

Quaint Home, Near Good Harbor Beach and Town, Great for Families

3
1.0
8

Gloucester Massachusetts Private vacation home Click For Pricing

GOT BEACH! Good Harbor House

GOT BEACH! Good Harbor House

4
4.0
8

Gloucester Massachusetts Private vacation home From $800 per night (USD)

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
3.0
8

Gloucester Massachusetts Cottage From $475 per night (USD)

Turning Tide Cottage on the Rivier

Turning Tide Cottage on the Rivier

3
2.0
5

Gloucester Massachusetts Private vacation home Click For Pricing

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

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

1
1.0
3

Gloucester Massachusetts Apartment From $130 per night (USD)

$Charming cottage near the ocean w\/beach access & near Gloucester$

Charming cottage near the ocean w\/beach access & near Gloucester

2
1.0
6

Gloucester Massachusetts Cottage From $322 per night (USD)

Cape Ann, Annisquam panoramic ocean views from every room.

Cape Ann, Annisquam panoramic ocean views from every room.

4
2.0
11

Gloucester Massachusetts Private vacation home From $571 per night (USD)

Walk to Good Harbor and Long Beach -Vacation Home

Walk to Good Harbor and Long Beach -Vacation Home

3
3.0
7

Gloucester Massachusetts Private vacation home From $400 per night (USD)

Clean Waterfront Classic Cottage with Private Beach

Clean Waterfront Classic Cottage with Private Beach

4
1.0
7

Gloucester Massachusetts Private vacation home From $415 per night (USD)

$Quaint Neighborhood \/ Close to Beaches$

Quaint Neighborhood \/ Close to Beaches

3
1.0
5

Gloucester Massachusetts Apartment From $215 per night (USD)

Annisquam Village Bunny Cottage

Annisquam Village Bunny Cottage

1
1.0
1

Gloucester Massachusetts Private vacation home From $225 per night (USD)

$Amazing Waterfront\/Access 4BDRM in Riggs Point$

Amazing Waterfront\/Access 4BDRM in Riggs Point

4
1.0
8

Gloucester Massachusetts Cottage From $397 per night (USD)

$Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!\n$

Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!\n

3
1.0
5

Gloucester Massachusetts Private vacation home From $435 per night (USD)

Downtown Dahlias fully remodeled in the heart of Gloucester

Downtown Dahlias fully remodeled in the heart of Gloucester

3
1.0
7

Gloucester Massachusetts Private vacation home From $410 per night (USD)

Prime Gloucester Property Overlooking Inner Harbor

Prime Gloucester Property Overlooking Inner Harbor

2
2.0
6

Gloucester Massachusetts Apartment From $267 per night (USD)

$Steps to Downtown Gloucester & A\/C throughout the house$

Steps to Downtown Gloucester & A\/C throughout the house

2
1.0
4

Gloucester Massachusetts Private vacation home From $270 per night (USD)

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

6
3.0
15

Gloucester Massachusetts Private vacation home From $775 per night (USD)

Walk to Good Harbor Beach. 3BR home, NEW Kitchen

Walk to Good Harbor Beach. 3BR home, NEW Kitchen

3
3.0
8

Gloucester Massachusetts Private vacation home From $338 per night (USD)

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

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

1
1.0
4

Gloucester Massachusetts Cottage From $150 per night (USD)

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches.

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches.

2
2.0
6

Gloucester Massachusetts Apartment From $386 per night (USD)

$Perfect Good Harbor Beach vacation home for large and\/or extended family getaway$

Perfect Good Harbor Beach vacation home for large and\/or extended family getaway

5
6.0
16

Gloucester Massachusetts Private vacation home From $709 per night (USD)

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

4
3.0
7

Gloucester Massachusetts Private vacation home From $654 per night (USD)

Historic cottage is steps from the beach on a glorious seaside estate!

Historic cottage is steps from the beach on a glorious seaside estate!

3
1.0
5

Gloucester Massachusetts Private vacation home Click For Pricing

The Captain’s Villa Beachfront House With Access To Pavilion's Beach

The Captain’s Villa Beachfront House With Access To Pavilion's Beach

4
5.0
12

Gloucester Massachusetts Villa From $912 per night (USD)

Long Beach House: Large, comfortable home just 285 ft from the white sands!

Long Beach House: Large, comfortable home just 285 ft from the white sands!

5
3.0
10

Gloucester Massachusetts Private vacation home From $791 per night (USD)

Newly renovated OCEAN-FRONT luxury home on private beach

Newly renovated OCEAN-FRONT luxury home on private beach

5
3.0
8

Gloucester Massachusetts Private vacation home From $1432 per night (USD)

Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.

Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.

4
4.0
10

Gloucester Massachusetts Private vacation home From $591 per night (USD)

Golden Sands at Good Harbor: Just walk across the street to the beach.

Golden Sands at Good Harbor: Just walk across the street to the beach.

7
4.0
12

Gloucester Massachusetts Private vacation home From $887 per night (USD)

Harbor View House, Walk to Beach, Sunsets from Deck

Harbor View House, Walk to Beach, Sunsets from Deck

2
1.0
6

Gloucester Massachusetts Private vacation home From $290 per night (USD)

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Annisquam Singing Pines: Private riverfront setting & tidal dock.

5
2.0
10

Gloucester Massachusetts Private vacation home From $756 per night (USD)

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

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

3
2.0
8

Gloucester Massachusetts Private vacation home From $562 per night (USD)

Luxury Accommodations in Quiet Seaside Village

Luxury Accommodations in Quiet Seaside Village

1
1.0
2

Gloucester Massachusetts Apartment From $179 per night (USD)

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

2
1.0
4

Gloucester Massachusetts Apartment From $230 per night (USD)

Sea Fox: Custom-designed home with rights to private Coffins Beach.

Sea Fox: Custom-designed home with rights to private Coffins Beach.

4
3.0
8

Gloucester Massachusetts Private vacation home From $689 per night (USD)

Coastal Oasis with Unobstructed, Direct Ocean Views!

Coastal Oasis with Unobstructed, Direct Ocean Views!

4
2.0
8

Gloucester Massachusetts Apartment From $837 per night (USD)

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

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

3
2.0
6

Gloucester Massachusetts Private vacation home From $475 per night (USD)

Seaside House: Good Harbor Beach and the Back Shore right outside your door.

Seaside House: Good Harbor Beach and the Back Shore right outside your door.

4
3.0
10

Gloucester Massachusetts Private vacation home From $733 per night (USD)

Rarely Available Ocean Facing Walkable to Good Harbor Beach

Rarely Available Ocean Facing Walkable to Good Harbor Beach

1
1.0
4

Gloucester Massachusetts Apartment From $552 per night (USD)

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

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

4
2.0
8

Gloucester Massachusetts Private vacation home From $395 per night (USD)

Breeze of Gloucester

Breeze of Gloucester

2
1.0
6

Gloucester Gloucester Private vacation home From $249 per night (USD)

WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park

WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park

1
2.0
2

Gloucester Massachusetts Condo From $350 per night (USD)

Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam

3
2.0
6

Gloucester Massachusetts Private vacation home From $448 per night (USD)

Cozy, Waterview Old Quarryman boarding house

Cozy, Waterview Old Quarryman boarding house

1
1.0
5

Gloucester Massachusetts Apartment From $175 per night (USD)

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit

5
2.0
12

Gloucester Massachusetts Private vacation home From $458 per night (USD)

Two Beaches: Walk to Long Beach or Good Harbor!

Two Beaches: Walk to Long Beach or Good Harbor!

3
2.0
8

Gloucester Massachusetts Private vacation home From $468 per night (USD)

Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.

Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.

3
2.0
6

Gloucester Massachusetts Private vacation home From $381 per night (USD)

Plaisance: Enjoy the best of Gloucester living.

Plaisance: Enjoy the best of Gloucester living.

3
3.0
8

Gloucester Massachusetts Private vacation home From $537 per night (USD)

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

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

2
1.0
4

Gloucester Massachusetts Apartment From $331 per night (USD)

Jewel Box: A gem of a rental home close to Good Harbor Beach.

Jewel Box: A gem of a rental home close to Good Harbor Beach.

2
1.0
3

Gloucester Massachusetts Private vacation home From $274 per night (USD)

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

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

2
3.0
6

Gloucester Massachusetts Private vacation home From $399 per night (USD)

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

3
2.0
7

Gloucester Massachusetts Private vacation home From $379 per night (USD)

Helena House: European flair, close to Plum Cove Beach.

Helena House: European flair, close to Plum Cove Beach.

3
3.0
7

Gloucester Massachusetts Private vacation home From $322 per night (USD)

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.

3
2.0
6

Gloucester Massachusetts Private vacation home From $338 per night (USD)

Squam Light: A newly renovated cottage, nestled in the village of Annisquam.

Squam Light: A newly renovated cottage, nestled in the village of Annisquam.

3
2.0
9

Gloucester Massachusetts Private vacation home From $371 per night (USD)

The Haabah Beach Retreat—4 Minute Walk to Beach

The Haabah Beach Retreat—4 Minute Walk to Beach

2
2.0
6

Gloucester Massachusetts Private vacation home From $540 per night (USD)

VIEWS! Annisquam Bridge House at Lobster Cove. Booking Spring and Summer

VIEWS! Annisquam Bridge House at Lobster Cove. Booking Spring and Summer

2
1.0
4

Gloucester Massachusetts Apartment From $191 per night (USD)

NEW Rental: 2 min walk to Private Coffin's Beach

NEW Rental: 2 min walk to Private Coffin's Beach

3
2.0
10

Gloucester Massachusetts Private vacation home From $857 per night (USD)

Walk to Good Harbor Beach, pet friendly, family beach home

Walk to Good Harbor Beach, pet friendly, family beach home

3
2.0
8

Gloucester Massachusetts Private vacation home From $300 per night (USD)

Wingaerchic: A hidden retreat near Gloucester's sandy Wingaersheek Beach.

Wingaerchic: A hidden retreat near Gloucester's sandy Wingaersheek Beach.

3
3.0
6

Gloucester Massachusetts Private vacation home From $410 per night (USD)

Sand Castle. 2 King beds, AC, outdoor shower. Walk to 2 local beaches

Sand Castle. 2 King beds, AC, outdoor shower. Walk to 2 local beaches

8
2.0
16

Gloucester Massachusetts Private vacation home From $720 per night (USD)

$Nature Lover's Paradise: cozy couples\/families, near town, nature walks, HiSpeed WiFi, 3 Smart TVs$

Nature Lover's Paradise: cozy couples\/families, near town, nature walks, HiSpeed WiFi, 3 Smart TVs

2
1.0
4

Gloucester Massachusetts Private vacation home From $272 per night (USD)

Spacious Modern Beach House- Steps to Long Beach and Good Harbor

Spacious Modern Beach House- Steps to Long Beach and Good Harbor

4
5.0
10

Gloucester Massachusetts Private vacation home From $600 per night (USD)

Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.

Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.

2
1.0
4

Gloucester Massachusetts Private vacation home From $255 per night (USD)

Good Harbor Beachfront at the Footbridge

Good Harbor Beachfront at the Footbridge

6
2.0
10

Gloucester Massachusetts Private vacation home From $714 per night (USD)

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

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

2
1.0
4

Gloucester Massachusetts Apartment From $186 per night (USD)

Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access

Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access

5
3.0
11

Gloucester Massachusetts Private vacation home From $514 per night (USD)

Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE

Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE

4
2.0
9

Gloucester Massachusetts Private vacation home From $817 per night (USD)

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

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

3
3.0
6

Gloucester Massachusetts Private vacation home From $385 per night (USD)

Summer Cottage on Ipswich Bay

Summer Cottage on Ipswich Bay

4
3.0
8

Gloucester Massachusetts Cottage From $526 per night (USD)

$\Rocky Neck Hideaway\ on Wonson Cove, Rocky Neck - Gloucester$

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

1
1.0
3

Gloucester, Massachusetts Private vacation home From $163 per night (USD)

Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI

Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI

3
2.0
6

Gloucester Massachusetts Private vacation home From $315 per night (USD)

Bayview Guest Cottage

Bayview Guest Cottage

2
2.0
3

Gloucester Massachusetts Cottage From $395 per night (USD)

Private, Single Family Beach House, Right at Good Harbor Beach foot bridge

Private, Single Family Beach House, Right at Good Harbor Beach foot bridge

3
1.0
8

Gloucester Massachusetts Cottage From $210 per night (USD)

Gloucester Studio - Om Suite Om~ near Good Harbor Beach

Gloucester Studio - Om Suite Om~ near Good Harbor Beach

1
1.0
2

Gloucester Massachusetts Apartment From $108 per night (USD)

Seaside Village of Lanesville - North Gloucester, MA

Seaside Village of Lanesville - North Gloucester, MA

2
1.0
4

Gloucester Massachusetts Apartment From $322 per night (USD)

Private, Light Filled & Convenient Wingaersheek Beach Home

Private, Light Filled & Convenient Wingaersheek Beach Home

3
1.0
6

Gloucester Massachusetts Private vacation home Click For Pricing

Evensong: Oceanview Retreat with Dock

Evensong: Oceanview Retreat with Dock

3
3.0
6

Gloucester Massachusetts Private vacation home From $598 per night (USD)

Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.

Charming cottage, four bedroom, sleeps six, near beach, in Gloucester, MA.

4
3.0
6

Gloucester Massachusetts Private vacation home From $325 per night (USD)

Load More Results