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Gloucester

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Vacation Rentals in Gloucester, Cape Ann

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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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20 Trusted Gloucester Area Rentals
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Traveller Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews | Just Added
1-20 of 20
Private Spacious Waterfront Home Luxury 6 B/R Pool, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Private Spacious Waterfront Home Luxury 6 B/R Pool
Slideshow
4.5 of 5 stars 2 reviews
  • Holiday Rental House
  • 6 Bedrooms, sleeps 12
  • 3 Bathrooms
  • Owner
EMAIL OWNER
Night:
667 AUD
Week:
4,516 AUD - 5,029 AUD
Minimum rental - 1 week
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Good Harbor House Vacation Rental. Gloucester, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Good Harbor House Vacation Rental. Gloucester
Slideshow
4.5 of 5 stars 10 reviews
  • Holiday Rental House
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Owner
EMAIL OWNER
Week:
1,206 AUD - 1,411 AUD
Minimum rental - 1 week
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Vacation Home/Spectacular Ocean Views and Sunsets, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Vacation Home/Spectacular Ocean Views and Sunsets
Slideshow
4.5 of 5 stars 7 reviews
  • Holiday Rental House
  • 4 Bedrooms, sleeps 10
  • 2 Bathrooms
  • Owner
EMAIL OWNER
Week:
3,028 AUD
Month:
2,053 AUD
Minimum rental - 1 week
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Lanes Cove Apartment, Contemporary and Affordable, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Lanes Cove Apartment, Contemporary and Affordable
Slideshow
4.5 of 5 stars 6 reviews
  • Condo/Apartment
  • 1 Bedroom, sleeps 3
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
103 AUD - 132 AUD
Week:
718 AUD - 924 AUD
Month:
924 AUD
Minimum rental - 1 week
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SUMMERWIND COTTAGE- Scenic Harbor View/Large Deck, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
SUMMERWIND COTTAGE- Scenic Harbor View/Large Deck
Slideshow
4 of 5 stars 3 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
180 AUD
Week:
1,232 AUD - 1,437 AUD
Minimum rental - 1 week
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Gloucester (Lanesville) Cottage, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Gloucester (Lanesville) Cottage
Slideshow
4 of 5 stars 2 reviews
  • Holiday Rental House
  • 3 Bedrooms, sleeps 5
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Week:
924 AUD
Month:
2,925 AUD
Minimum rental - 1 week
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Wonderful Oceanside Carriage House Vacations, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Wonderful Oceanside Carriage House Vacations
Slideshow
4 of 5 stars 7 reviews
  • Holiday Rental House
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
1,437 AUD - 1,847 AUD
Month:
1,232 AUD
Minimum rental - 1 week
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Gloucester, MA, inner harbor with deep water dock, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Gloucester, MA, inner harbor with deep water dock
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 7
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
462 AUD
Minimum rental - 1 week
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Magnolia Elegant Georgian near Beach, Gloucester - JUST ADDED
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Magnolia Elegant Georgian near Beach
Slideshow
  • Holiday Rental House
  • 8 Bedrooms, sleeps 18
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
667 AUD - 872 AUD
Week:
4,516 AUD - 5,952 AUD
Minimum rental - 1 night
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Casually Elegant Georgian in Downtown Gloucester, Gloucester
Massachusetts, Cape Ann, Gloucester Holiday Rentals
Casually Elegant Georgian in Downtown Gloucester
  • Holiday Rental House
  • 8 Bedrooms, sleeps 19
  • 6 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
924 AUD
Week:
5,131 AUD
Minimum rental - 2 nights
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The following rentals are within 10 kilometres of Gloucester, Cape Ann, Massachusetts.

Rockport, MA One Bedroom Carriage House, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
Rockport, MA One Bedroom Carriage House
4 of 5 stars 4 reviews
  • Condo/Apartment
  • 1 Bedroom, sleeps 3
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
128 AUD - 164 AUD
Week:
872 AUD - 1,026 AUD
Month:
1,283 AUD
Minimum rental - 3 nights
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Sea Mist Cottage, walk downtown, private yard., Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
Sea Mist Cottage, walk downtown, private yard.
Slideshow
4.5 of 5 stars 10 reviews
  • Holiday Rental House
  • Studio, sleeps 5
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
113 AUD - 122 AUD
Week:
693 AUD - 974 AUD
Month:
2,822 AUD - 3,797 AUD
Minimum rental - 2 nights
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Rockport Dock Square Jewel - 1 Bedroom Apartment, Rockport - JUST ADDED
Massachusetts, Cape Ann, Rockport Holiday Rentals
Rockport Dock Square Jewel - 1 Bedroom Apartment
Slideshow
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Owner
EMAIL OWNER
Night:
180 AUD
Week:
1,232 AUD
Minimum rental - 1 week
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Mary's By The Sea, 14 Beach Street, 978-500-7956, Rockport - JUST ADDED
Massachusetts, Cape Ann, Rockport Holiday Rentals
Mary's By The Sea, 14 Beach Street, 978-500-7956
Slideshow
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Verified owner
EMAIL OWNER
Night:
200 AUD
Week:
1,385 AUD
Minimum rental - 2 nights
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A Seaside Retreat with Oceanfront Pool, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
A Seaside Retreat with Oceanfront Pool
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
512 AUD
Week:
1,847 AUD - 1,976 AUD
Minimum rental - 1 week
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Summer Cottage Rental, Rockport Mass. USA, Rockport - JUST ADDED
Massachusetts, Cape Ann, Rockport Holiday Rentals
Summer Cottage Rental, Rockport Mass. USA
  • Holiday Rental House
  • 9 Bedrooms, sleeps 14
  • 4 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
733 AUD
Week:
5,131 AUD
Month:
20,525 AUD
Minimum rental - 1 week
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Old Garden Beach charmer steps to Bearskin Neck!, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
Old Garden Beach charmer steps to Bearskin Neck!
Slideshow
  • Holiday Rental House
  • 3 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
1,539 AUD - 2,309 AUD
Minimum rental - 1 week
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Relaxing 5 BR Waterfront Vacation Rental, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
Relaxing 5 BR Waterfront Vacation Rental
Slideshow
  • Holiday Rental House
  • 5 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Verified owner
EMAIL OWNER
Night:
366 AUD
Week:
2,566 AUD - 4,100 AUD
Minimum rental - 1 week
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ROCKY SHORES-SEASIDE COTTAGE, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
ROCKY SHORES-SEASIDE COTTAGE
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 1 Bathroom
  • Owner
EMAIL OWNER
Week:
1,847 AUD
Minimum rental - 1 week
Check availability
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Beach & King Street Inn / Beach House Rental, Rockport
Massachusetts, Cape Ann, Rockport Holiday Rentals
Beach & King Street Inn / Beach House Rental
Slideshow
  • Holiday Rental House
  • 6 Bedrooms, sleeps 14
  • 5 Bathrooms
  • Verified owner
EMAIL OWNER
Week:
3,900 AUD - 4,926 AUD
Month:
2,874 AUD
Minimum rental - 1 week
Check availability
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1-20 of 20

Gloucester Holiday Rental Advice

Condo-cottages near the Cape Ann Motor Inn
Posted by snorkelgirlie, 31 Dec 2008
... I am searching for a vacation rental. From reading this forum, I understand there is a cottage/condo community near the Cape Ann Motor Inn and I was wondering if anyone knew contact information on how to book them. I'm having a bit of a hard time finding an ... more
looking for a small house to rent on good harbor beach front
Posted by eric r, 14 Aug 2011
... a house and not a condo or just a room. if any one have answers or internet link i would really appreciate the help.by the way left early friday morning(4:00 a.m.)to boston and came back to canada (1 hour past montreal) sunday after noon stopping ... more
Gloucester or Hyannis MAsssachusetts
Posted by BlueNova, 3 Aug 2007
... ever since, even bought a condo there. Cape Cod, the other Cape (Gloucester is in Cape Ann), is just to touristy and too, too crowded with traffic. Gloucester is quaint, much less crowded and the water at the beaches is crystal clear unlike Cape Cod's where the warmer water ... more
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