filters

Search results; Over 1,000 homes in Gloucester

Photo 1 of 29
Top guest favourite
Guest house in Gloucester
Annisquam Village Bunny Cottage
1 bedroom, 1 bed, 1 private bathroom
2–7 Nov
,
4.97 out of 5 average rating, 319 reviews
Photo 1 of 21
Featured hotel
Hotel in Gloucester
Ocean House Hotel at Bass Rocks, Deluxe two queen.
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
New place to stay
Photo 1 of 29
Home in Gloucester
Good Harbor Beach Bridge
3 bedrooms, 6 beds, 1 bathroom
2–7 Nov
Photo 1 of 29
Top guest favourite
Flat in Gloucester
New Downtown Gloucester Condo
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 29 reviews
Photo 1 of 29
Guest favourite
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
4 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.94 out of 5 average rating, 48 reviews
Photo 1 of 29
Guest favourite
Home in Gloucester
Buoy 23 Vacation Home Rentals
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 10 reviews
Photo 1 of 29
Top guest favourite
Apartment in Rockport
Rockport Getaway near ocean, music hall & downtown
2 bedrooms, 3 beds, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 110 reviews
Photo 1 of 29
Guest favourite
Home in Gloucester
Charming Harbor View Home
2 bedrooms, 3 beds, 1.5 bathrooms
22–29 Apr
5.0 out of 5 average rating, 25 reviews
Photo 1 of 29
Top guest favourite
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 bedrooms, 3 beds, 3.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 33 reviews
Photo 1 of 14
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
1 bedroom, 2 beds, 1 bathroom
14–19 Nov
4.96 out of 5 average rating, 162 reviews
Photo 1 of 17
Top guest favourite
Guest house in Rockport
Seagull’s Nest
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 65 reviews
Photo 1 of 28
Top guest favourite
Home in Gloucester
William Haskell House First Period Colonial Home
4 bedrooms, 3 queen beds, 2 bathrooms
28 Nov – 3 Dec
5.0 out of 5 average rating, 37 reviews
Photo 1 of 25
Camper van/Motorhome in Gloucester
Glamping Airstream 5 Private Acres Ocean Views
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
New place to stay
Photo 1 of 21
Top guest favourite
Flat in Gloucester
Sunsets on the Seawall
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
4.93 out of 5 average rating, 14 reviews
Photo 1 of 29
Top guest favourite
Flat in Rockport
Harbor Views in the Heart of Rockport
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 69 reviews
Photo 1 of 24
Superhost
Home in Gloucester
Stay in Central Gloucester
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Nov
New place to stay
Photo 1 of 29
Guest favourite
Home in Gloucester
House on tidal river, spacious deck, private yard
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 18 reviews
Photo 1 of 21
Top guest favourite
Home in Gloucester
Swim in Summer, Ski in Winter—Waterfront Sunsets!
4 bedrooms, 5 beds, 2 bathrooms
3–8 Nov
4.98 out of 5 average rating, 61 reviews
Photo 1 of 29
Guest favourite
Home in Gloucester
Luxury 5BR Family Retreat | Walk to Beach & Town
5 bedrooms, 6 beds, 4 bathrooms
6–11 Dec
4.97 out of 5 average rating, 150 reviews