
Holiday rentals in Gloucester
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Top-rated holiday rentals in Gloucester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Gloucester holiday rentals
Other great holiday rentals in Gloucester
Top guest favourite

Flat in Gloucester
5 out of 5 average rating, 8 reviewsCoastal Escape with Harbor Views
Guest favourite

Flat in Rockport
5 out of 5 average rating, 12 reviewsThe Pearl, Apt. #2
Superhost

Home in Gloucester
4.75 out of 5 average rating, 8 reviewsCoastal Comfort—Walk to Beach & Cafés
Guest favourite

Home in Annisquam
4.97 out of 5 average rating, 33 reviewsAnnisquam Getaway - Water View+Walk To The Beach

Flat in Gloucester
5 out of 5 average rating, 4 reviewsCape Ann Summer Beach! King beds. Private parking!
Guest favourite

Home in Gloucester
4.95 out of 5 average rating, 39 reviewsTownhouse #3 in Downtown with Parking
Guest favourite

Apartment in Gloucester
4.93 out of 5 average rating, 30 reviewsThe BLVD Gloucester Harbor&RiverViews
Guest favourite

Flat in Gloucester
4.96 out of 5 average rating, 46 reviewsCozy Apartment at Green Landing (No Cleaning Fee)
Quick stats about holiday rentals in Gloucester
Total rentals
590 properties
Total number of reviews
25K reviews
Family-friendly rentals
380 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Destinations to explore
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Hudson Valley Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
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- Jersey Shore Holiday rentals
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- Philadelphia Holiday rentals
- Family-friendly rentals Gloucester
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- York Harbor Beach
- Duxbury Beach
- New England Aquarium
- North Hampton Beach
- Faneuil Hall Marketplace
- Good Harbor Beach
- Crane Beach
- Freedom Trail
- Canobie Lake Park
- Long Sands Beach
- MIT Museum
- Prudential Center
- Rye North Beach
- Museum of Fine Arts, Boston
- Bear Brook State Park