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Search results; Over 1,000 homes in Gloucester

Top guest favourite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
Studio, 1 bed, 1 private bathroom
17–22 Oct
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4.92 out of 5 average rating, 239 reviews
Guest favourite
Home in Gloucester
2 bdrm house on the water, watch tide ebb and flow
2 bedrooms, 2 queen beds, 1 bathroom
31 Aug – 5 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Gloucester
Private 2BR Near Downtown, Beaches & Restaurants
2 bedrooms, 6 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
New place to stay
Top guest favourite
Flat in Gloucester
Boulevard Retreat
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Gloucester
Folly Cove Shoreline
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 14 reviews
Guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
10–15 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Gloucester
Luxury 5BR Home + Office, Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
29 Aug – 3 Sept
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Flat in Rockport
Waterfront Condo/Heart Of Rockport/Bearskin Neck
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Gloucester
The Fort: On the Beau Port
2 bedrooms, 2 beds, 1 bathroom
4–9 Jul
5.0 out of 5 average rating, 53 reviews
Superhost
Home in Gloucester
Sunset Serenity-Entire Cozy Home-30 min to Salem
2 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Rockport
Downtown Cottage
2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
5.0 out of 5 average rating, 7 reviews
Guest favourite
Apartment in Gloucester
Retreat to tranquility - water views
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Rockport
4 Bed Water View w/ Parking
4 bedrooms, 5 beds, 2 bathrooms
25–30 Oct
4.99 out of 5 average rating, 167 reviews
Top guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 94 reviews
Guest favourite
Flat in Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.87 out of 5 average rating, 167 reviews
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Flat in Gloucester
Walk to Downtown & Harbor | Patio Grill | King Bed
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Gloucester
Quaint Neighborhood / Close to Beaches
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 168 reviews