Gloucester Vacation Home Rentals from CA $718: 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 marina with boats docked at the pier, reflecting the sunset sky.

1. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

East Gloucester

Hillary M.

CA $618 total

includes taxes & fees

Sep 2 - Sep 3

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

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

Gloucester

Melenia s.

CA $532 total

includes taxes & fees

Sep 9 - Sep 10

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

CA $575 total

includes taxes & fees

Sep 21 - Sep 22

A spacious living room with a large window, a sofa, a coffee table, a chair, and a TV mounted on the wall.

4. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

East Gloucester

Michele V.

CA $798 total

includes taxes & fees

Sep 22 - Sep 23

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

5. The Essex of Gloucester

Gloucester

Katie B.

CA $387 total

includes taxes & fees

Sep 21 - Sep 22

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

6. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

CA $917 total

includes taxes & fees

Sep 3 - Sep 4

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

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

Gloucester

Maarij K.

CA $1,296 total

includes taxes & fees

Aug 31 - Sep 1

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

8. Beach Life Bliss - steps to the beach

Gloucester

rich k.

CA $845 total

includes taxes & fees

Sep 9 - Sep 10

A living room with a fireplace, sofas, a TV, and wooden beams on the ceiling.

9. Stay at Good Harbor Beach

East Gloucester

hawley s.

CA $3,824 total

includes taxes & fees

Sep 8 - Sep 9

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

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

Gloucester

Sara G.

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

Maryanne H.

CA $796 total

includes taxes & fees

Sep 17 - Sep 18

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.

CA $865 total

includes taxes & fees

Sep 7 - Sep 8

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

CA $737 total

includes taxes & fees

Sep 27 - Sep 28

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

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

Salisbury Beach

Shannon S.

CA $578 total

includes taxes & fees

Aug 31 - Sep 1

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

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

Rockport

Emmy D.

CA $1,067 total

includes taxes & fees

Sep 9 - Sep 10

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

16. 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.

CA $1,035 total

includes taxes & fees

Sep 9 - Sep 10

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

17. 2BR Historic Marblehead Home+Minutes to Beach

Marblehead Historic District

Kevin H.

CA $592 total

includes taxes & fees

Sep 7 - Sep 8

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

18. 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 $798 total

includes taxes & fees

Sep 28 - Sep 29

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

19. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

Denitsa a.

CA $955 total

includes taxes & fees

Sep 28 - Sep 29

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

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

Marblehead

Katherine B.

CA $822 total

includes taxes & fees

Sep 1 - Sep 2

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Top Gloucester Hotel Reviews

Sonesta Select Boston Danvers

8/10 Good

"Couch is a bit worn and ripped, light bulb kept flashing. Other than that great!"

Holiday Inn Hotel & Suites Boston - Peabody by IHG

10/10 Excellent

"The hotel is nice for what it is, which is affordable and in relative location to tons of stuff, including near Salem, without paying Salem prices. It could definitely use an update, there were definitely some cosmetic issues with the property and the rooms, but for the price you pay, it's very clean, it's very comfortable, and the staff was great. I would definitely stay here again."

Ocean House Hotel at Bass Rocks

10/10 Excellent

"The room was wonderful- clean and had a deck right off of our slider & we were steps away from a beautiful pool and hot tub. The staff were friendly and helpful. The views of the water crashing on the rocks were amazing and there were chairs set up to sit and enjoy. There was a firepit and they served cookies and coffee in the afternoon & cheese and wine in the early evening. There was a nice breakfast in the morning serving spinach and feta or ham and cheese hot croissants, fruit and bagels and eggs. I would rate our experience a 10 out of 10. Will definitely come again."

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews	7
Accommodation	522 Vacation Homes
Lowest Price	CA $718
Highest Price	CA $1,447

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gloucester vacation homes

1. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

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

3. Cozy two bedroom house in the heart of Gloucester