Holiday rentals in Gloucester

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Top-rated holiday rentals in Gloucester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Home in Gloucester
Rocky Neck Retreat 4 Bedroom/2Bath/Kitchen/Laundry
.Relaxing private location .4 beds 2 baths with full kitchen/pans/Dishwasher/Wash/Dryer.Renovated organic design integrates historic architecture with modern touches.If you come for hikes, beach/music/food scene, you will enjoy the Rocky Neck District .The unique home has 4 bedrooms /4 Queen Beds. Speedy WIFI .Parking is up a steep narrow drive . NO trucks or Large SUVs. 2 cars max. Note* Kitchen and LR are upstairs.There are stairs. Contact owner for questions re:parking or limited mobility.
15–22 Sept
£505 per night
4.99 out of 5 average rating, 153 reviews
Guest favourite
Apartment in Rockport
6 Tuna Wharf - Harbor right outside kitchen door!
Dreaming of summer vacation in Rockport? This condo is in the middle of the action and excitement of Bearskin Neck yet private & directly on the wharf. Classy beachy condo overlooking Rockport Harbor & Motif 1. Steps from shops, beaches, restaurants, art galleries & beaches. Outside the kitchenette, a private patio on the wharf for morning coffee, grilling or evening happy hour. Relax and watch the boats go by year round! A fun getaway even in the off season. Book early to secure your trip!
17–24 FebIndividual Host,
£329 per night
4.99 out of 5 average rating, 184 reviews
Superhost
Guest suite in Gloucester
Guest suite in historical district
You'll enjoy a private 3rd-floor guest suite in this gorgeous 1853 Italianate-style house in the historical district of downtown Gloucester. We occupy the 1st & 2nd floors of the house. Short walking distance to restaurants, bars, bakeries, shops, museums & the working harbor. A stone's throw from Beauport Hotel & Cruiseport wedding venues, Stacy Boulevard with Man at the Wheel statue, Pavillion Beach, Stage Fort Park & Half Moon Beach. Easy stroll to the train station if you're coming by train.
6–13 Dec
£119 per night
4.84 out of 5 average rating, 25 reviews

Popular amenities for Gloucester holiday rentals

Stay near Gloucester's top sights

Cape Ann Whale Watch41 locals recommend
Beauport Hotel Gloucester35 locals recommend
7 Seas Whale Watch19 locals recommend
Stage Fort Park and Beach45 locals recommend
Causeway Restaurant41 locals recommend
Seaport Grill31 locals recommend

Other great holiday rentals in Gloucester

Guest favourite
Apartment in Rockport
In Town One Room Studio-Walk to Shops/Beaches
2–9 DecIndividual Host,
£109 per night
4.89 out of 5 average rating, 37 reviews
Guest favourite
Cottage in Gloucester
waterview guest suite
10–17 Oct
£153 per night
4.86 out of 5 average rating, 29 reviews
Guest favourite
Guest suite in Gloucester
Sunsets at the Seawall - A Coastal Hideaway
1–8 Dec
£189 per night
5.0 out of 5 average rating, 44 reviews
Guest favourite
Flat in Gloucester
Beautifully remodeled unit in heart of Gloucester
22–29 Nov
£209 per night
4.96 out of 5 average rating, 71 reviews
Guest favourite
Apartment in Gloucester
Key West Vibe,PrivatePatio,New Reno,WalkDWNTN
1–8 FebProfessional Host,
£157 per night
4.97 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Gloucester
Sunny & private cottage in Lanesville Village
12–19 NovIndividual Host,
£248 per night
4.97 out of 5 average rating, 98 reviews
Guest favourite
Flat in Rockport
Little Apartment by the Sea
22–29 Jan
£136 per night
5.0 out of 5 average rating, 29 reviews
Guest favourite
Guest suite in Gloucester
Walk to Good Harbor Beach and Downtown Gloucester
14–21 Jul
£181 per night
5.0 out of 5 average rating, 85 reviews
Guest favourite
Home in Gloucester
Seaside Home Minutes to Rockport and Gloucester!
26 Apr – 3 May
£167 per night
4.93 out of 5 average rating, 55 reviews
Guest favourite
Holiday home in Gloucester
Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace
6–13 Jul
£526 per night
5.0 out of 5 average rating, 31 reviews
Guest favourite
Home in Gloucester
Overlook Gloucester's Inner Harbor, Walk to Town
19–26 DecIndividual Host,
£422 per night
4.97 out of 5 average rating, 68 reviews
Guest favourite
Home in Gloucester
4 plus bedrms 5 baths- 3 level Beachfront House.
14–21 Apr
£802 per night
4.95 out of 5 average rating, 22 reviews

Quick stats about holiday rentals in Gloucester

Total rentals

530 properties

Rentals with dedicated workspaces

240 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

130 properties allow pets

Family-friendly rentals

320 properties are a good fit for families

Total number of reviews

22K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester