Gloucester Holiday Homes from £223: Search Holiday Homes in Gloucester

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

1. The Essex of Gloucester

Gloucester

Katie B.

includes taxes & fees

19 Oct - 20 Oct

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

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

Gloucester

Karen T.

includes taxes & fees

28 Sept - 29 Sept

A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

3. Cozy two bedroom house in the heart of Gloucester

Gloucester

CHARLES

includes taxes & fees

27 Sept - 28 Sept

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

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

Gloucester

Maarij K.

includes taxes & fees

27 Sept - 28 Sept

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

5. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

includes taxes & fees

7 Oct - 8 Oct

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

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

Gloucester

Sara G.

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

7. Stay at Rocky Neck

Rocky Neck

Joy B.

includes taxes & fees

12 Oct - 13 Oct

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

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

Rockport

Angela G.

includes taxes & fees

27 Sept - 28 Sept

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

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

Rockport

Bridget H.

includes taxes & fees

20 Oct - 21 Oct

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

10. 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

includes taxes & fees

28 Sept - 29 Sept

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

11. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

Denitsa a.

includes taxes & fees

28 Sept - 29 Sept

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.

12. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

includes taxes & fees

7 Oct - 8 Oct

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

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

Rockport

Emmy D.

includes taxes & fees

29 Sept - 30 Sept

A living room with a sofa, a television displaying a cartoon, a staircase, and a wooden cabinet.

14. HOT TUB I Downtown Rockport w/parking I Sleeps 8

Rockport

"This beach house was everything we were looking for. We had a great family vacation second year in a row at one of Rachel’s great properties in Rockport.The house was perfectly clean, cool, and well equipped for cooking and grilling and enjoying the beautiful outdoor area. The hot tub was a fun bonus and the best surprise was the outdoor shower which made getting home from the beach trips with little kids breezy.We walked to the beach and Bearskin Neck easily each day.The host is on top of every...

Kelli S.

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

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

Rockport

Juliet S.

includes taxes & fees

6 Oct - 7 Oct

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

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

Rockport

Danielle L.

includes taxes & fees

21 Oct - 22 Oct

A beach with a sunset, rocky shoreline, and calm waters.

17. Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

Manchester-by-the-Sea

Colorado B.

includes taxes & fees

30 Sept - 1 Oct

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

includes taxes & fees

30 Sept - 1 Oct