Gloucester Vacation Home Rentals from CA $291: Search Top Private Vacation Homes for Rent

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 vacation 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.

CA $497 total

includes taxes & fees

Oct 20 - Oct 21

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.

CA $291 total

includes taxes & fees

Nov 3 - Nov 4

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.

CA $733 total

includes taxes & fees

Nov 4 - Nov 5

A residential property with a well-maintained lawn, a stone retaining wall, and a wooden deck.

4. 3BR Harborside Home • Gloucester+Rockport • Ocean View

East Gloucester

Valerie N.

CA $981 total

includes taxes & fees

Oct 19 - Oct 20

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.

CA $1,276 total

includes taxes & fees

Oct 26 - Oct 27

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.

CA $1,538 total

includes taxes & fees

Oct 20 - Oct 21

A waterfront property with a dock, a covered seating area, and a view of the marina and surrounding houses.

7. Stay at The Neck

Rocky Neck

Jack J.

CA $1,726 total

includes taxes & fees

Oct 26 - Oct 27

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

8. Stay at Little River

Gloucester

Caitlin D.

CA $1,734 total

includes taxes & fees

Oct 15 - Oct 16

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

9. 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

CA $589 total

includes taxes & fees

Nov 8 - Nov 9

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

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

Rockport

Maryanne H.

CA $877 total

includes taxes & fees

Nov 3 - Nov 4

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.

11. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

CA $942 total

includes taxes & fees

Nov 4 - Nov 5

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

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

Rockport

Danielle L.

CA $1,261 total

includes taxes & fees

Nov 11 - Nov 12

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

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

Rockport

Kelley S.

CA $1,230 total

includes taxes & fees

Oct 31 - Nov 1

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

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

Rockport

Juliet S.

CA $1,322 total

includes taxes & fees

Oct 25 - Oct 26

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

laura r.

CA $1,410 total

includes taxes & fees

Oct 20 - Oct 21

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

16. 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

CA $566 total

includes taxes & fees

Oct 15 - Oct 16