Search results; Over 1,000 places in Gloucester

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Guest favorite
Guest suite in Gloucester
SplashLanding Private Beach Getaway in Gloucester
2 guests1 bedroom2 beds1 bath
Apr 15 – 20
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Apr 15 – 20
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ﺩ.ﺇ 5,768 for 5 nights
for 5 nights

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Guest favorite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
1 double bed
May 17 – 22
ﺩ.ﺇ 2,469 for 5 nights
for 5 nights
4.9 out of 5 average rating, 194 reviews
Guest favorite
Room in Gloucester
Stay with DawnArtist,
Annisquam Artist Oasis -Serene Private Upstairs
May 4 – 9
ﺩ.ﺇ 2,669 for 5 nights
for 5 nights
4.92 out of 5 average rating, 228 reviews
Cottage in Rockport
Bearskin Neck Old Garden Beach
Free cancellation
May 11 – 16
ﺩ.ﺇ 3,955 for 5 nights
for 5 nights
5.0 out of 5 average rating, 3 reviews
Home in Gloucester
Luxury Starboard Townhome Steps to Niles Beach
3 beds
May 3 – 8
ﺩ.ﺇ 18,490 for 5 nights
for 5 nights
New place to stay
Top guest favorite
Apartment in Gloucester
Blue Magnolia
3 beds
May 4 – 9
ﺩ.ﺇ 4,736 for 5 nights
for 5 nights
5.0 out of 5 average rating, 29 reviews
Top guest favorite
Bungalow in Gloucester
mermaid surf bungalow on good harbor beach
Free cancellation
May 17 – 24
ﺩ.ﺇ 11,000 for 7 nights
for 7 nights
4.98 out of 5 average rating, 58 reviews
Guest favorite
Guest suite in Gloucester
Simple, Charming Private Space Central Gloucester
2 beds
May 18 – 23
ﺩ.ﺇ 3,357 for 5 nights
for 5 nights
4.9 out of 5 average rating, 77 reviews
Top guest favorite
Vacation home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
3 beds
May 3 – 8
ﺩ.ﺇ 9,148 for 5 nights
for 5 nights
5.0 out of 5 average rating, 48 reviews
Apartment in Gloucester
Seafood, Sunsets + Seaside Charm
2 beds
May 4 – 9
ﺩ.ﺇ 4,521 for 5 nights
for 5 nights
4.93 out of 5 average rating, 27 reviews
Top guest favorite
Condo in Gloucester
3BR Oceanfront Condo with decks
5 beds
May 10 – 15
ﺩ.ﺇ 6,638 for 5 nights
for 5 nights
4.99 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Gloucester
Charming Retreat / Close to Beaches
Free cancellation
Jul 6 – 11
ﺩ.ﺇ 6,302 for 5 nights
for 5 nights
4.86 out of 5 average rating, 44 reviews
Guest favorite
Loft in Gloucester
Downtown, Shops, Beach, Deck, Close to Salem
3 beds
May 5 – 10
ﺩ.ﺇ 3,477 for 5 nights
for 5 nights
4.98 out of 5 average rating, 157 reviews
Top guest favorite
Guest suite in Gloucester
Live Like a Local, Just Steps From The Beach
Free cancellation
Jun 12 – 17
ﺩ.ﺇ 4,929 for 5 nights
for 5 nights
4.95 out of 5 average rating, 79 reviews
Guest favorite
Apartment in Gloucester
Tiny studio by the Annisquam River
2 single beds
May 4 – 9
ﺩ.ﺇ 2,368 for 5 nights
for 5 nights
4.92 out of 5 average rating, 174 reviews
Guest favorite
Apartment in Rockport
Artistic studio with garden, walk to town/beaches
1 queen bed
May 3 – 8
ﺩ.ﺇ 2,280 for 5 nights
for 5 nights
5.0 out of 5 average rating, 27 reviews
Guest favorite
Condo in Gloucester
Smith Cove Cottage Condo
Free cancellation
Jun 22 – 27
ﺩ.ﺇ 5,265 for 5 nights
for 5 nights
4.96 out of 5 average rating, 27 reviews
Guest favorite
Apartment in Gloucester
Bright One Bedroom Apartment 5 Min Walk From Beach
2 beds
May 3 – 8
ﺩ.ﺇ 5,682 for 5 nights
for 5 nights
4.88 out of 5 average rating, 137 reviews
Top guest favorite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
Free cancellation
May 10 – 15
ﺩ.ﺇ 9,298 for 5 nights
for 5 nights
4.98 out of 5 average rating, 82 reviews