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 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.

HK$2,173 total

includes taxes & fees

4 Nov - 5 Nov

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.

HK$3,521 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

3. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

East Gloucester

Nina R.

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.

HK$7,617 total

includes taxes & fees

27 Oct - 28 Oct

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

5. Beach Life Bliss - steps to the beach

Gloucester

Nicole

HK$6,456 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Stay at The Neck

Rocky Neck

Jack J.

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

7. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

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

Kelley S.

HK$6,139 total

includes taxes & fees

31 Oct - 1 Nov

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

Maryanne H.

HK$3,641 total

includes taxes & fees

17 Nov - 18 Nov

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

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.

HK$4,924 total

includes taxes & fees

2 Nov - 3 Nov

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

12. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

laura r.

HK$5,798 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Rockport

Danielle L.

HK$7,323 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Manchester-by-the-Sea

Colorado B.

HK$5,141 total

includes taxes & fees

27 Oct - 28 Oct

A covered outdoor patio with Adirondack chairs, a stone wall, and a pathway leading to a seating area.

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

Rockport

Joan L.

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

16. Historic Marblehead Nautical Home • Minutes to Salem

Marblehead Historic District

Kevin H.

HK$3,717 total

includes taxes & fees

27 Oct - 28 Oct

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

17. 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$3,378 total

includes taxes & fees

3 Nov - 4 Nov

A kitchen with light-colored cabinets, a black stove, and a gray backsplash.

18. Moody Salem Home Away From Home

Salem

Margaret G.

HK$5,117 total

includes taxes & fees

27 Oct - 28 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

"We stayed in the property for one night, so we were in and out. The house is older, but everything works great and it was super clean. The beds were very comfortable. The view from the back year/deck is simply amazing. The ocean, the lighthouse, the boats are just beautiful and is worth every bit of what we paid. I didn’t have a need to communicate with the host but all check in and check out directions were sufficient."

Hayley H.

HK$4,853 total

includes taxes & fees

16 Nov - 17 Nov

A two-story beach house with a balcony, a deck, and a sign reading "Plovers Nest".

20. Plovers Nest

Newburyport

Anat

HK$3,146 total

includes taxes & fees

9 Nov - 10 Nov

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Top Gloucester Hotel Reviews

Holiday Inn Hotel & Suites Boston - Peabody by IHG

8/10 Good

"Location ok, staff was ok, AC was hard to control, did have dirty towels in room after check in."

DoubleTree by Hilton Boston North Shore

10/10 Excellent

"Great stay! Even if it’s for one night I noticed the hotel was very clean staff was very helpful. They upgraded our room with no extra charge because they didn’t have the room I picked available. Loved the upgrade! And!! We got cookies as a welcome! Will be staying again if we are in town."

Hawthorne Hotel

8/10 Good

"It’s an old hotel, so don’t expect modern day upgrades in the rooms. The hotel IS great. Our room was good. A few things wrong with room but no bad, sort of. Our a/c unit didn’t work, so we had to leave the window open our entire 4 day stay. Not bad. There IS, also, a big window in the shower, which is facing the street. Talk about putting a show for all those outside. Our room had a great view, and so did the outside looking in. It’s even worse when showering, or using bathroom at night. Beware room 420. Besides those two things, for the time we actually used the room, it was great. Bar, restaurant, free coffee, tea, and water. Concierge service. It’s a great hotel, and it’s in a great location. Everything is walking distance. I’d stay here again."

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