Top Winter Vacations - Vacation Rentals in Maritime Gloucester

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From US $471

         

10.0 (142 Reviews)

House

WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $535

         

New

Apartment

The Chill-a-Vista

• Air Conditioner
• Parking
• Child Friendly

• Massachusetts
• Gloucester

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From US $211

         

|

9.6 (315 Reviews)

Bed & Breakfast

Harborview Inn

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $675

         

10.0 (47 Reviews)

House

PREMIUM PROPERTY - Private 2-Acre Retreat - MODERN 4 Bedrooms - See Video Tour

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $396

         

|

10.0 (7 Reviews)

House

The Buoys

• Air Conditioner
• Parking
• View

• Massachusetts
• Gloucester

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From US $227

         

|

9.6 (907 Reviews)

Hotel

Beauport Hotel Gloucester

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Gloucester

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From US $212

         

9.8 (83 Reviews)

House

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $1,094

         

|

10.0 (3 Reviews)

House

Stay at Rocky Neck

• Air Conditioner
• Parking
• Security/Safety

• Massachusetts
• Gloucester

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From US $268

         

|

9.6 (468 Reviews)

Hotel

Atlantis Oceanfront Inn

• Air Conditioner
• Parking
• Pool

• Massachusetts
• Gloucester

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From US $708

         

10.0 (66 Reviews)

House

Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $245

         

10.0 (135 Reviews)

House

Romantic Summerwind Cottage, Scenic Harbor View w/Large Deck

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $555

         

10.0 (219 Reviews)

Cottage

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

• Air Conditioner
• Parking
• Pet Friendly

• Massachusetts
• Gloucester

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From US $714

         

9.8 (14 Reviews)

House

Two Beaches: Long Beach & Good Harbor

• Parking
• TV
• View

• Massachusetts
• Gloucester

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From US $725

         

9.4 (12 Reviews)

House

Sage Hill: Long Beach & More!

• Air Conditioner
• Pet Friendly
• TV

• Massachusetts
• Rockport

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From US $840

         

9.4 (22 Reviews)

House

Thurston Point: Deepwater River Dock

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $312

         

10.0 (72 Reviews)

House

WALK TO BEACH! Great Location! Booking 2026! Close to Salem!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $383

         

10.0 (56 Reviews)

House

5-star home with quick walk to 2 beaches!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $460

         

10.0 (49 Reviews)

House

Evensong: Oceanview Retreat with Dock

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $244

         

10.0 (48 Reviews)

Apartment

WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $247

         

10.0 (46 Reviews)

House

Single Level Home - Steps to Downtown Gloucester & A/C throughout

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $361

         

10.0 (38 Reviews)

House

Stay at Niles Beach

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $1,115

         

10.0 (37 Reviews)

House

Ocean front and 3 beaches across,parks, short walk to historic downtown!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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From US $348

         

10.0 (37 Reviews)

House

Newly Renovated Luxury 5BR Home + Office, Walk to Beach & Town

• Parking
• Security/Safety
• Bedding/Linens

• Massachusetts
• Gloucester

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From US $159

         

10.0 (37 Reviews)

House

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

• Air Conditioner
• Parking
• TV

• Massachusetts
• Gloucester

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Maritime Gloucester.