Gloucester vacation rentals

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Top-rated vacation rentals in Gloucester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

  1. Entire guest suite
  2. Gloucester
Walk to Good Harbor Beach and Downtown Gloucester

Enjoy this separate entrance fully private apartment within easy walking access to Good Harbor beach, downtown Gloucester, and everything Cape Ann and the North Shore has to offer! This quiet and cozy place has everything you need for your sea-side stay.

$94 per night
SUPERHOST
  1. Private room
  2. Gloucester
Comfortable 1 Bedroom in a 2 Bedroom apartment

A comfortable, private one bedroom inside a 2 bedroom apartment shared with renter. Located in the center of Gloucester, my rental is walking distance to commuter train (.4 miles) and shopping/food areas. Gloucester is particularly beautiful during the spring and summer months! I am located only 1.1 miles from the gorgeous Stacy Boulevard and Pavilion Beach. Gloucester is also home to two other beaches voted "Best in New England" Good Harbor and Wingaerhseek !

$60 per night
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  1. Entire rental unit
  2. Gloucester
Spacious one bedroom apartment 10 min from beach

Spacious one bedroom apartment minutes from the beach. Nestled in the woods of west Gloucester, 5 minutes from hwy 128, 10 minutes from Wingaersheek beach, and 15 minutes from downtown Gloucester. Close to hiking trails, Dike's reservoir., and Agape Brewery. You'll enjoy coming back to this quiet space after visiting downtown Gloucester beaches, restaurants, and shopping

$91 per night

Vacation rentals for every style

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Gloucester summer vacation rentals

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  1. Entire rental unit
  2. Gloucester
Spacious Home with WideOpen Views of Gloc. Harbor
$145 per night
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  1. Entire guesthouse
  2. Gloucester
Jestina's Cottage - Next to Rocky Neck
$135 per night
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  1. Private room
  2. Gloucester
Cape Ann Guest and Retreat House-Gloucester Room
$99 per night
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  1. Entire cottage
  2. Manchester-by-the-Sea
Singing Beach Cottage in Manchester by the Sea
$93 per night
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  1. Entire loft
  2. Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
$104 per night
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  1. Entire rental unit
  2. Rockport
Charming Rockport Studio Apt
$93 per night
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  1. Entire rental unit
  2. Rockport
Newly Renovated 2Bdrm Rockport
$99 per night
  1. Entire rental unit
  2. Gloucester
Prime location to Beauport Hotel & Beach, Glo Apt
$200 per night
  1. Entire condo
  2. Rockport
Gorgeous apartment, short walk to beach&downtown!
$179 per night
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  1. Entire rental unit
  2. Gloucester
Walk to Good Harbor Beach
$150 per night
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  1. Entire home
  2. Gloucester
Wonderful Rocky Neck home on Gloucester harbor
$326 per night
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  1. Entire guest suite
  2. Rockport
Nature lovers retreat. host is FULLY VACCINATED
$105 per night

Gloucester winter vacation rentals

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  1. Entire rental unit
  2. Gloucester
Charming Rocky Neck Rental - No cleaning fee!
$165 per night
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  1. Private room
  2. Gloucester
Cape Ann Guest and Retreat House- Rockport Room
$99 per night
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  1. Entire cottage
  2. Gloucester
Cute Cottage with harbor views in a great location
$202 per night
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  1. Entire home
  2. Annisquam
Views! Annisquam Bridge House at Lobster Cove
$208 per night
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  1. Entire cottage
  2. Rockport
Quaint Oceanfront Cottage in Rockport MA
$135 per night
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  1. Entire rental unit
  2. Rockport
Sweet short term rental in Rockport
$140 per night
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  1. Entire rental unit
  2. Gloucester
White Sand beach in a private enclave
$200 per night
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  1. Entire loft
  2. Rockport
Loft Apartment With Ocean Views
$280 per night
  1. Entire rental unit
  2. Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
$204 per night
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  1. Private room
  2. Gloucester
Annisquam Artist Oasis -Serene Private Upstairs
$106 per night
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  1. Entire guest suite
  2. Gloucester
SplashLanding Private Beach Getaway in Gloucester
$249 per night
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  1. Private room
  2. Gloucester
Cozy Suite with Private Bath
$145 per night

Gloucester beach vacation rentals

  1. Entire guesthouse
  2. Annisquam
Annisquam Village Bunny Cottage
$225 per night
  1. Entire guest suite
  2. Gloucester
Funky room above convenience store, near water
$129 per night
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  1. Entire rental unit
  2. Rockport
Ocean View unit with Private Roofdeck in Rockport
$215 per night
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  1. Entire rental unit
  2. Rockport
Mary's By The Sea
$165 per night
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  1. Entire guest suite
  2. Gloucester
PrivateBeach for 2 Adults, Gloucester MA SquishInn
$199 per night
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  1. Entire rental unit
  2. Rockport
Captains Quarters @ The Sail Loft- Rockport
$141 per night
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  1. Entire rental unit
  2. Gloucester
The Center, A Seaside Urban Resort
$139 per night
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  1. Entire rental unit
  2. Gloucester
Amazing Ocean View In-Law Apt.
$245 per night
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  1. Entire rental unit
  2. Gloucester
Close to Half Moon Beach!
$154 per night
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  1. Entire rental unit
  2. Gloucester
Adorable Studio in Downtown Gloucester
$168 per night
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  1. Entire home
  2. Rockport
Carriage House on Historic Property
$214 per night
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  1. Private room
  2. Rockport
Seaside Gardens guest room private floor by beach
$121 per night