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$2,840 total

includes taxes & fees

20 Oct - 21 Oct

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

2. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

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

3. The Essex of Gloucester

Gloucester

Katie B.

HK$2,393 total

includes taxes & fees

4 Nov - 5 Nov

A spacious living room with a large window overlooking a body of water, a dining area with a table and chairs, and a cozy seating area with a sofa and coffee table.

4. Luxury Starboard Townhome Steps to Niles Beach

East Gloucester

HK$10,536 total

includes taxes & fees

13 Oct - 14 Oct

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

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

Gloucester

Karen T.

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 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.

HK$7,860 total

includes taxes & fees

6 Oct - 7 Oct

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.

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

9. Stay at Rocky Neck

Rocky Neck

Joy B.

A room with two sofas facing a central table, large windows with wooden frames, and a chandelier.

10. Edgemoor Estate - 11 Bed/6.5 Bath l Sleeps 32 - Pool, Hot Tub, Walk to Beach

East Gloucester

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

Bridget H.

HK$4,998 total

includes taxes & fees

26 Oct - 27 Oct

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

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

Rockport

Emmy D.

HK$6,825 total

includes taxes & fees

25 Oct - 26 Oct

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.

HK$4,963 total

includes taxes & fees

6 Oct - 7 Oct

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.

14. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

HK$5,199 total

includes taxes & fees

7 Oct - 8 Oct

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

15. 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.

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

Rockport

Juliet S.

HK$6,431 total

includes taxes & fees

7 Oct - 8 Oct

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

17. 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$4,664 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Rockport

Danielle L.

HK$8,152 total

includes taxes & fees

3 Nov - 4 Nov

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.

HK$7,296 total

includes taxes & fees

7 Oct - 8 Oct

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

20. 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$3,431 total

includes taxes & fees

7 Oct - 8 Oct

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Top Gloucester Hotel Reviews

Lakeside Inn

10/10 Excellent

"This was the coziest stay we had in the area."

The Northshore Hotel - Boston/Danvers

10/10 Excellent

"The room was very clean overall, with hard flooring rather than carpet, which I appreciated. The bathroom mirror appeared to have been overlooked during cleaning, but the rest of the room was clean and well maintained. If you tend to get cold, I recommend bringing or requesting an extra blanket. The towels were adequate—not plush, but perfectly serviceable. Only the basic number was provided, so women or anyone who prefers separate towels for their hair and body may want to request extras. There was also only one trash can, located outside the bathroom, but it was easy enough to move it into the bathroom when needed. The hotel was exactly what we needed for a few days in Salem and was only about 20 minutes away. It is beautifully nestled away from traffic and other noise. Because it is an older hotel that has been renovated, soundproofing between rooms is limited. If you are sensitive to noise, I recommend requesting a room without another guest directly above you. Overall, the property was clean and well maintained, and the staff was exceptionally kind. I enjoyed my stay and would definitely return."

Ocean House Hotel at Bass Rocks

10/10 Excellent

"The location of this hotel was incredible. Overlooking the ocean, with a large balcony, and a lovely walkway along the ocean. The room was large and clean and comfortable with a couch and seating area. The bathroom was small but adequate. We walked to the hotel next door for a nice breakfast. The pool area was inviting but too cool to enjoy when we went. We'd definitely go back."

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