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Search results; Over 1,000 homes in Gloucester

Top guest favourite

Home in Gloucester

Harbor View Walk to Beach & Town, 6Guests KingBeds

3 bedrooms, 4 beds, 2 private bathrooms

19–24 Aug

$5,782 SGD for 5 nights

,

4.97 out of 5 average rating, 151 reviews

Guest favourite

Home in Gloucester

Oceanfront Dock Escape ~ Kayaks & Paddleboards

4 bedrooms, 7 beds, 3 bathrooms

27 Aug – 1 Sept

Extended stay discount

4.95 out of 5 average rating, 41 reviews

Superhost

Flat in Gloucester

Stunning Ocean-View Retreat, Magnolia Beach

2 bedrooms, 2 king beds, 2 bathrooms

27 Aug – 1 Sept

$2,763 SGD for 5 nights

Top guest favourite

Flat in Gloucester

New Downtown Gloucester Condo

2 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

Free cancellation

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Flat in Gloucester

Blue Magnolia

2 bedrooms, 3 beds, 1 bathroom

23–28 Aug

$2,001 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 79 reviews

Superhost

Home in Ipswich

Direct Waterfront on Plum Island Sound Sunsets

2 bedrooms, 3 beds, 2 bathrooms

16–21 Sept

Book early to save

Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Gloucester

Lovely home by the sea!

3 bedrooms, 7 beds, 2.5 bathrooms

8–13 Sept

$4,744 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 19 reviews

Guest favourite

Home in Gloucester

Seaside Home|Sleeps 7|Plum Cove Beach+Rockport!

2 bedrooms, 5 beds, 2 bathrooms

1–6 Nov

$1,734 SGD for 5 nights

4.93 out of 5 average rating, 112 reviews

Guest favourite

Home in Gloucester

Private Beachfront Property in Gloucester

3 bedrooms, 3 beds, 3.5 bathrooms

4–9 Nov

$4,145 SGD for 5 nights

5.0 out of 5 average rating, 9 reviews

Top guest favourite

Home in Gloucester

Gloucester Private Contemporary 4 bedrooms

4 bedrooms, 5 beds, 2 bathrooms

23–28 Aug

$3,168 SGD for 5 nights

4.84 out of 5 average rating, 219 reviews

Guest favourite

Place to stay in Gloucester

Back Shore Hidden Garden Suite

3 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$2,435 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 78 reviews

Guest favourite

Home in Gloucester

Parsons at Stage Fort

3 bedrooms, 4 beds, 2 bathrooms

26–31 Aug

$3,918 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Top guest favourite

Home in Gloucester

Luxury 5BR Home + Office, Walk to Beach & Town

5 bedrooms, 6 beds, 4 bathrooms

14–19 Nov

4.99 out of 5 average rating, 140 reviews

Superhost

Home in Gloucester

Stay at Wingaersheek

3 bedrooms, 5 beds, 3.5 bathrooms

7–12 Sept

$6,502 SGD for 5 nights

New place to stay

Top guest favourite

Home in Gloucester

Annisquam Getaway - Water View+Walk To The Beach

3 bedrooms, 5 beds, 3 bathrooms

31 Aug – 5 Sept

$3,407 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 47 reviews

Superhost

Home in Gloucester

Stay at Good Harbor Beach

3 bedrooms, 4 beds, 2.5 bathrooms

10–15 Aug

$7,708 SGD for 5 nights

New place to stay

Top guest favourite

Home in Gloucester

Luxury Starboard Townhome Steps to Niles Beach

3 bedrooms, 3 beds, 3.5 bathrooms

27 Aug – 1 Sept

$8,057 SGD for 5 nights

5.0 out of 5 average rating, 24 reviews

Top guest favourite

Holiday home in Gloucester

On the Water Gem - 2 BR -The Cove Lanesville

2 bedrooms, 3 beds, 1 bathroom

2–7 Aug

$3,606 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 83 reviews

Top guest favourite

Home in Gloucester

Rocky Neck Retreat

4 bedrooms, 4 queen beds, 2 bathrooms

26–31 Aug

$2,950 SGD for 5 nights

4.99 out of 5 average rating, 222 reviews