House holiday rentals in Gloucester
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Top-rated house rentals in Gloucester
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Gloucester house rentals
House rentals with a pool
Home in North Andover
4.94 out of 5 average rating, 127 reviewsNana-tucket Inn
25 Nov – 2 Dec
Home in Kittery
4.92 out of 5 average rating, 100 reviewsQuiet Home with heated inground pool, waterfront
5–12 Jun
Home in Lawrence
4.95 out of 5 average rating, 63 reviewsCozy single family ranch style main floor
16–23 Jan
Home in Derry
4.88 out of 5 average rating, 88 reviewsSanctum by the Lake
7–14 Jan
Home in Nahant
4.97 out of 5 average rating, 67 reviewsHouse by the Sea - Glocca Morra
31 May – 7 Jun
Home in Revere
4.64 out of 5 average rating, 11 reviewsSeaside Serenity Boston -Pet Frndly+Htd Pool
15–22 Sep
Home in North Andover
4.98 out of 5 average rating, 51 reviewsBeautiful Farmhouse at Boutique Winery w/ Tasting
12–19 Sep
Home in Kittery
4.95 out of 5 average rating, 22 reviewsFantastic Kittery Home with Pool
15–22 Oct
Weekly house rentals
Home in Framingham
4.96 out of 5 average rating, 130 reviews2BR—Charming 1900s Home—1st Floor—25min to Boston
6–13 May
Home in Revere
4.79 out of 5 average rating, 140 reviewsRenovated Cozy City Getaway
30 Nov – 7 Dec
Home in Gloucester
5.0 out of 5 average rating, 18 reviewsCharming Harbor View Home
17–24 Apr
Home in Gloucester
4.91 out of 5 average rating, 11 reviewsRare 4BR Fully Renovated Oceanfront Home
6–13 May
Home in Gloucester
5.0 out of 5 average rating, 27 reviewsPavilion Beach Townhouse
29 Jan – 5 Feb
Home in Gloucester
4.97 out of 5 average rating, 86 reviewsCharming Year Round Home, Plum Cove Cottage
4–11 Oct
Home in Gloucester
4.94 out of 5 average rating, 17 reviewsGloucester Beach House
18–25 Jul
Home in Gloucester
5.0 out of 5 average rating, 29 reviewsNEWLY Renovated Luxury Home, Walk To Town & Beach
15–22 Jan
Private house rentals
Home in Rockport
5.0 out of 5 average rating, 68 reviewsWalk to The Beach/Bearskin At Historic Renovation
2–9 Nov
Home in Gloucester
5.0 out of 5 average rating, 20 reviewsBeach House The house on the boulevard
24 Sep – 1 Oct
Home in Gloucester
5.0 out of 5 average rating, 14 reviewsWalk to the Beach! Annisquam Diamond Cove Getaway
11–18 Nov
Home in Gloucester
4.97 out of 5 average rating, 98 reviewsHarbor View Walk to Town&Beach, 6 Guests King beds
31 Dec – 7 Jan
Home in Gloucester
4.82 out of 5 average rating, 22 reviewsEntire House in Beautiful, Historic Gloucester
25 Jul – 1 Aug
Home in Rockport
4.98 out of 5 average rating, 48 reviewsLarge Yard|Fire Table|6min walk DNTN|New
7–14 Jan
Home in Rockport
4.89 out of 5 average rating, 9 reviewsBreathtaking Renovated Rockport Home-Walk to Beach
26 Mar – 2 Apr
Home in Gloucester
5.0 out of 5 average rating, 11 reviewsWaterfront with Breathtaking Views & Private Dock
8–15 Oct
Quick stats about house rentals in Gloucester
Total rentals
240 properties
Wi-Fi availability
230 properties include access to Wi-Fi
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
210 properties are a good fit for families
Total number of reviews
6.2K reviews
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