Search results; Over 1,000 places in Gloucester

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Guest favorite
Home in Gloucester
Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets
14 guests4 bedrooms11 beds2 baths
May 17 – 22
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May 17 – 22
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G$210,965 GYD per night

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Top guest favorite
Guest suite in Gloucester
Walk to Good Harbor Beach and Downtown Gloucester
Free cancellation
May 18 – 23
G$25,649 GYD per night
4.99 out of 5 average rating, 128 reviews
Top guest favorite
Guest suite in Gloucester
Live Like a Local, Just Steps From The Beach
2 queen beds
Apr 13 – 18
G$28,705 GYD per night
4.95 out of 5 average rating, 74 reviews
Guest favorite
Guesthouse in Gloucester
Annisquam Village Bunny Cottage
1 queen bed
Apr 5 – 10
G$54,159 GYD per night
4.97 out of 5 average rating, 260 reviews
Top guest favorite
Vacation home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
3 beds
May 3 – 8
G$85,758 GYD per night
5.0 out of 5 average rating, 48 reviews
Guest favorite
Apartment in Gloucester
Charming Retreat / Close to Beaches
2 beds
Apr 25 – 30
G$25,690 GYD per night
4.9 out of 5 average rating, 39 reviews
Superhost
Home in Rockport
4BR Oceanfront Rockport Vacation on Long Beach!
4 beds
Apr 13 – 18
G$91,182 GYD per night
4.86 out of 5 average rating, 44 reviews
Top guest favorite
Home in Gloucester
NEWLY Renovated Luxury Home, Walk To Town & Beach
6 beds
Jun 1 – 6
G$121,290 GYD per night
4.99 out of 5 average rating, 80 reviews
Guest favorite
Apartment in Gloucester
East Gloucester Beach house
4 beds
May 1 – 6
G$46,531 GYD per night
4.86 out of 5 average rating, 28 reviews
Home in Gloucester
Gloucester getaway ocean escape
Free cancellation
Apr 30 – May 5
G$48,782 GYD per night
4.78 out of 5 average rating, 153 reviews
Superhost
Home in Gloucester
The Edgemoor Estate
13 beds
Apr 4 – 9
G$233,600 GYD per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Apartment in Gloucester
Beautifully remodeled unit in heart of Gloucester
2 beds
Apr 6 – 11
G$45,892 GYD per night
4.96 out of 5 average rating, 113 reviews
Top guest favorite
Guesthouse in Gloucester
Charming Guesthouse with Access to Private Beach
1 queen bed
Apr 26 – May 1
G$33,628 GYD per night
4.94 out of 5 average rating, 62 reviews
Top guest favorite
Home in Gloucester
Panoramic Ocean View; walk to private beach
Free cancellation
Apr 24 – 29
G$64,761 GYD per night
4.98 out of 5 average rating, 48 reviews
Superhost
Guesthouse in Gloucester
Plum Cove Cottage with king suite!
2 beds
Apr 6 – 11
G$25,949 GYD per night
4.92 out of 5 average rating, 88 reviews
Guest favorite
Apartment in Gloucester
CbytheSea - Ocean View Penthouse
2 beds
Apr 6 – 11
G$32,091 GYD per night
4.98 out of 5 average rating, 43 reviews
Superhost
Home in Gloucester
Oceanfront Dock Escape ~ Kayaks & Paddleboards
7 beds
Apr 4 – 9
G$51,394 GYD per night
Guest favorite
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
Free cancellation
Oct 13 – 18
G$42,370 GYD per night
4.97 out of 5 average rating, 125 reviews
Top guest favorite
Home in Gloucester
Elegant Bayview Victorian Home; walk to beach
Free cancellation
Apr 14 – 19
G$49,720 GYD per night
5.0 out of 5 average rating, 21 reviews