Gloucester Vacation Homes

A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

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Our top choices for Gloucester holiday homes

A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

1. Beach Life Bliss - steps to the beach

Gloucester

rick b.

HK$2,866 total

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

2. The Essex of Gloucester

Gloucester

Katie B.

HK$1,604 total

includes taxes & fees

3 Nov - 4 Nov

A staircase with wooden steps leading to a room with a wooden ceiling.

3. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Gloucester

Karen T.

HK$4,105 total

includes taxes & fees

4 Nov - 5 Nov

A wooden staircase with a railing leading to a covered deck area.

4. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

HK$5,970 total

includes taxes & fees

7 Oct - 8 Oct

A bedroom with a bed, bedside tables, a desk, and a bench.

5. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Gloucester

Sara G.

HK$5,233 total

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

6. Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester

Maarij K.

HK$7,842 total

includes taxes & fees

6 Oct - 7 Oct

A spacious living room with a large TV, comfortable seating, and large windows offering a view of the outdoors.

7. Stay at Little River

Gloucester

Caitlin D.

HK$8,652 total

includes taxes & fees

15 Oct - 16 Oct

A two-story residential building with a garage, a driveway, and a well-maintained lawn.

8. Luxury Starboard Townhome Steps to Niles Beach

East Gloucester

HK$10,945 total

includes taxes & fees

13 Oct - 14 Oct

A waterfront property with a dock, a small house with a balcony, and a larger house with a garage.

9. Stay at Rocky Neck

Rocky Neck

Joy B.

HK$13,315 total

includes taxes & fees

12 Oct - 13 Oct

A spacious living area with a large TV, a kitchen, and a dining area.

10. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Rockport

Kelley S.

HK$4,663 total

includes taxes & fees

6 Oct - 7 Oct

A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

11. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport

Bridget H.

HK$4,772 total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

12. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Rockport

Emmy D.

HK$6,372 total

includes taxes & fees

8 Oct - 9 Oct

A spacious living room with a high ceiling, wooden beams, a sofa, a blue armchair, a coffee table, and a dining area with a table and chairs.

13. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

HK$5,199 total

includes taxes & fees

7 Oct - 8 Oct

A large, two-story house with a steeply pitched roof, surrounded by lush greenery and a view of the sea.

14. Experience Classic New England-walk to beach&shops

Rockport

Danielle L.

HK$8,301 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with blue sofas, a wooden coffee table, and large windows with white curtains.

15. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

Denitsa a.

HK$6,726 total

includes taxes & fees

6 Oct - 7 Oct

A stone fire pit surrounded by Adirondack chairs in a landscaped area with a stone wall and a large tree.

16. Home w/firepit l Walk to Bearskin Neck+Beach

Rockport

Juliet S.

A beach with people sunbathing and swimming, a rocky outcrop in the foreground, and a small island in the background.

17. Bell Buoy

Rockport

"The property is nicely located but in need of updates. A lot of the lamps are plug in vs light switch and there were some flickering lights behind the TV. One lamp was missing a light bulb. No outlet in the bathroom for a hair dryer. The second bathroom is missing a door handle making it hard to open and close. We were unable to reach the ceiling fan chain without having to get on the bed, The Air Conditioner wasn't working on he first floor which made it a bit stuff but with open windows at...

Amy

A beach with a wooden fence, sand, and the ocean.

18. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Salisbury Beach

"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...

Maura

HK$3,158 total

includes taxes & fees

19 Oct - 20 Oct

A room with a large window overlooking a wooden deck with white railings and a lighthouse in the distance.

19. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Marblehead

Katherine B.

HK$5,408 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

20. Historic Marblehead Nautical Home • Minutes to Salem

Marblehead Historic District

Kevin H.

HK$5,626 total

includes taxes & fees

12 Oct - 13 Oct

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Top Gloucester Hotel Reviews

Extended Stay America Suites Boston Peabody

8/10 Good

"It was an acceptable stay"

DoubleTree by Hilton Boston North Shore

10/10 Excellent

"This is a no frills hotel, that is nevertheless excellent. The reception staff is lovely and greets you with warm, homemade chocolate chip/walnut cookies (after check in!) The rooms are spotless, the linens crisp and clean & the beds are nice & firm. The large TV includes Netflix, Hulu & HBO which was very nice for some distraction in the evening. But the very best part if this hotel is the exceptional Sports Club and Pool and Jacuzzi all of which the hotel guests have access to during their stay. And you should take advantage! Also, there is an unassuming restaurant/bar on the main floor and the food is surprisingly good. I had glazed salmon and spring vegetables and it was outstanding! For breakfast they have both a Continental or A la Carte menus depending on your choice and a small Starbucks open for a few hours, as well. Enjoy."

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