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$6,461 total

includes taxes & fees

1 Nov - 2 Nov

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$2,235 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Gloucester

Maarij K.

HK$7,701 total

includes taxes & fees

19 Oct - 20 Oct

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

4. 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

HK$3,252 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Rockport

Maryanne H.

HK$4,106 total

includes taxes & fees

4 Nov - 5 Nov

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

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

Rockport

Emmy D.

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.

7. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

HK$5,198 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Rockport

Danielle L.

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

9. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

laura r.

HK$6,848 total

includes taxes & fees

20 Oct - 21 Oct

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

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

Rockport

Juliet S.

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

11. 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$3,192 total

includes taxes & fees

19 Oct - 20 Oct