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

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

Gloucester

Karen T.

HK$3,279 total

includes taxes & fees

11 Nov - 12 Nov

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.

HK$1,604 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Gloucester

Betty

HK$5,827 total

includes taxes & fees

2 Nov - 3 Nov

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$7,081 total

includes taxes & fees

3 Nov - 4 Nov

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

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

East Gloucester

Nina R.

HK$6,228 total

includes taxes & fees

24 Nov - 25 Nov

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

6. Beach Life Bliss - steps to the beach

Gloucester

Nicole

A wooden deck with a table and chairs, overlooking a body of water and a distant building.

7. Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Gloucester

Stacey W.

HK$6,403 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Rockport

Maryanne H.

HK$3,794 total

includes taxes & fees

17 Nov - 18 Nov

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.

9. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

HK$4,925 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Rockport

Joan L.

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

11. Plovers Nest

Newburyport

Anat

HK$3,147 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Manchester-by-the-Sea

Colorado B.

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

13. 4 BR Home l Walk to Beaches & Downtown l Reserved Parking & Beach Gear included

Rockport

laura r.

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

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

Rockport

Danielle L.

HK$7,308 total

includes taxes & fees

11 Nov - 12 Nov

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

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

Rockport

Kelley S.

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

HK$2,874 total

includes taxes & fees

2 Nov - 3 Nov

A dining room with a wooden table set for four, a chandelier, and a large mirror.

17. Brackett Cottage: Near Salem! Heart of Historic Marblehead; Walk to Shops & Dining

Marblehead Historic District

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

18. Historic Marblehead Nautical Home • Minutes to Salem

Marblehead Historic District

Kevin H.

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

19. Moody Salem Home Away From Home

Salem

Margaret G.

HK$10,261 total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with a sofa, a dining table, and a kitchen area with cabinets and a refrigerator.

20. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

Salisbury Beach

HK$3,401 total

includes taxes & fees

2 Nov - 3 Nov

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Top Gloucester Hotel Reviews

The Northshore Hotel - Boston/Danvers

10/10 Excellent

"I have zero complaints about my stay. The room was clean, comfortable, and quiet. I checked in around 10 p.m. the gorgeous young lady at the front desk couldn't have been more nice and helpful."

Ashworth by the Sea

8/10 Good

"Parking is charged upon check-in but there was no parking. Anywhere. First off. They force valet upon you, even if you do not want it, or your car 3 blocks away. They have a few spots Under their building and the employees appear to use those. We drove around for an hour waiting for them for have an opening. It was 9pm. And their bar seemed to have all of the spots taken up. Our entire take out dinner got cold and soggy in the process and it was ny husbands birthday. 100$ worth of food. Eventually we used a pay to park across the street and walked to the hotel. For this reason alone, I would not stay there again. Got parking refunded through hotels.com"

Ocean House Hotel at Bass Rocks

10/10 Excellent

"This is one of the best New England stays I’ve had. The location is everything — The photos don’t do it justice. You’re right on the water. There is an outdoor fire pit and hammocks that we used as it was COLD and windy when we went. We still enjoyed every minute of this place. Pool and hot tub looked beautiful but we did not brave the late fall temperatures and give them a try. We were greeted by freshly baked cookies upon front desk check in. Excellent continental breakfast options. Loved this stay."

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