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

4.99 out of 5 average rating, 153 reviews

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.

20–27 Sept

£527 per night
Guest favourite

Flat in Beverly

4.92 out of 5 average rating, 446 reviews

Private apartment 10 min to Salem!

This private entrance basement apartment is within a 1/2 mile to several beautiful Beverly beaches. Downtown Beverly is about a 10 to 15 minute pleasant walk. It offers great restaurants and cafes. Live entertainment is happening almost nightly at the Larcom and Cabot theaters. Endicott College is 1 mile away. Downtown Salem is about a ten minute drive from here. The train to Boston, Salem, or Rockport is about a mile away. Plenty of safe street parking is available in front of my house.

7–14 Apr

£111 per night
Superhost

Guest suite in Beverly

4.85 out of 5 average rating, 656 reviews

Historic North Shore, private suite & bathroom

Minutes from Salem! Relax in historic Beverly (walk to Beverly shops) in your private suite; bedroom, living room, and small bathroom, connected to our home, but private entrance. Just minutes from Salem. Commuter line to Boston and close to beautiful North Shore beaches and historic sites. Beaches within biking and driving distances, downtown, parks, hiking. Comfy, soft king bed, queen pull out couch, and plenty of linens. Great for couples, solo adventurers, business travelers, and families.

11–18 Sept

£114 per night

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

4.89 out of 5 average rating, 37 reviews

In Town One Room Studio-Walk to Shops/Beaches

30 Apr – 7 May

£103 per night
Superhost

Guest suite in Gloucester

4.84 out of 5 average rating, 25 reviews

Guest suite in historical district

19–26 Jan

£120 per night
Guest favourite

Guest suite in Gloucester

5.0 out of 5 average rating, 44 reviews

Sunsets at the Seawall - A Coastal Hideaway

11–18 Dec

£200 per night
Guest favourite

Flat in Gloucester

4.96 out of 5 average rating, 71 reviews

Beautifully remodeled unit in heart of Gloucester

23–30 Jul

£211 per night
Guest favourite

Cottage in Gloucester

4.86 out of 5 average rating, 29 reviews

waterview guest suite

19–26 Oct

£154 per night
Superhost

Flat in Gloucester

4.83 out of 5 average rating, 90 reviews

Amazing Ocean View In-Law Apt.

8–15 Feb

£239 per night
Guest favourite

Guest suite in Gloucester

5.0 out of 5 average rating, 85 reviews

Walk to Good Harbor Beach and Downtown Gloucester

7–14 Aug

£182 per night
Guest favourite

Apartment in Gloucester

4.97 out of 5 average rating, 90 reviews

Key West Vibe,PrivatePatio,New Reno,WalkDWNTN

26 Feb – 5 Mar

£171 per night
Guest favourite

Holiday home in Gloucester

5.0 out of 5 average rating, 31 reviews

Gorgeous Oceanfront 2-Bdrm Apartment w/ Fireplace

6–13 Jul

£531 per night
Guest favourite

Flat in Rockport

5.0 out of 5 average rating, 29 reviews

Little Apartment by the Sea

30 Aug – 6 Sept

£138 per night
Guest favourite

Cottage in Gloucester

4.97 out of 5 average rating, 98 reviews

Sunny & private cottage in Lanesville Village

1–8 Nov

£248 per night
Guest favourite

Home in Gloucester

4.97 out of 5 average rating, 69 reviews

Overlook Gloucester's Inner Harbor, Walk to Town

10–17 Jan

£426 per night

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

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