Vacation Rentals in Gloucester, MA: Compare 10+ Sites & Save

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  3.  USA

  4.  Massachusetts

  5.  Gloucester

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388 Best Vacation Rentals in Gloucester (Starting from $173)

Gloucester Harbor Hideaway
Gloucester Harbor Hideaway
Apartment
Gloucester, MA, USA
0.1k from Gloucester center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

2 Bedrooms4 Guests
9.4

Superb

5 reviews

$402
Average price / night
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Centrally located open concept apartment with parking,  central AC, & W/D
Centrally located open concept apartment with parking, central AC, & W/D
Apartment
Gloucester, MA, 01930, United States
0.1k from Gloucester center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.8

Exceptional

22 reviews

$476
Average price / night
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Guest suite in historical district
Guest suite in historical district
Apartment
Gloucester, MA, USA
0.2k from Gloucester center

Parking, Air Conditioner, Security/Safety, Guest Services, Internet, Sports/Activities, Breakfast

2 Bedrooms4 Guests
9.1

Superb

43 reviews

$180
Average price / night
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Townhouse in Downtown Gloucester #2
Townhouse in Downtown Gloucester #2
House
Gloucester, MA, 01930, United States
0.3k from Gloucester center

AC, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking, TV

3 Bedrooms6 Guests
New to Booking
$463
Average price / night
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Stay at Rocky Neck
Stay at Rocky Neck
House
Gloucester, MA, USA
0.6k from Gloucester center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms7 Guests
10.0

Exceptional

1 reviews

$1093
Average price / night
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Open concept, 2-level apartment with scenic view
Open concept, 2-level apartment with scenic view
Apartment
Gloucester, MA, 01930, United States
0.4k from Gloucester center

Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Toys

2 Bedrooms4 Guests
New to Booking
$392
Average price / night
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A by the Bay - Stunning Seaside Apartment
A by the Bay - Stunning Seaside Apartment
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

2 Bedrooms6 Guests
9.2

Superb

25 reviews

$559
Average price / night
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Harbortown Hideaway: Downtown Gloucester Charm
Harbortown Hideaway: Downtown Gloucester Charm
Apartment
Gloucester, MA, 01930, United States
0.5k from Gloucester center

AC, Barbecue, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$577
Average price / night
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Spacious 2nd floor Suite
Spacious 2nd floor Suite
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering, Beach rentals

2 Bedrooms4 Guests
7.1

Good

7 reviews

$173
Average price / night
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Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Apartment
Gloucester, MA, 01930, United States
0.5k from Gloucester center

AC, Crib, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

12 reviews

$416
Average price / night
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Glorious Suite near Downtown with washer/dryer
Glorious Suite near Downtown with washer/dryer
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms4 Guests
8.7

Fabulous

19 reviews

$291
Average price / night
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Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck
Tranquil 7-bedroom house with Ocean views in Gloucester's charming Rocky Neck
House
Gloucester, MA, 01930, United States
0.5k from Gloucester center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Microwave, No Smoking

7 Bedrooms18 Guests
10.0

Exceptional

4 reviews

$1273
Average price / night
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Bianca's House
Bianca's House
House
Gloucester, MA, USA
0.8k from Gloucester center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
6.0

Review score

3 reviews

$326
Average price / night
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Longview House
Longview House
House
Gloucester, MA, USA
0.8k from Gloucester center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family, Accessible hotels

4 Bedrooms9 Guests
6.0

Review score

2 reviews

$383
Average price / night
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Waterway View; Steps to Ocean, Beach, Blvd, Park
Waterway View; Steps to Ocean, Beach, Blvd, Park
House
Gloucester, MA, 01930, United States
0.6k from Gloucester center

AC, Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms9 Guests
New to Booking
$979
Average price / night
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Stay at The Neck
Stay at The Neck
House
Gloucester, MA, USA
0.8k from Gloucester center

Air Conditioner, Security/Safety, Sports/Activities, Fireplace/Heating, Internet, Parking, Child Friendly

1 Bedroom7 Guests
New to Booking
$444
Average price / night
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Elevated Fish & Ships on Canal: Walk to Beach,Park
Elevated Fish & Ships on Canal: Walk to Beach,Park
Apartment
Gloucester, MA, 01930, United States
0.6k from Gloucester center

Balcony, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms5 Guests
New to Booking
$367
Average price / night
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The Chill-a-Vista
The Chill-a-Vista
Apartment
Gloucester, Massachusetts, USA
0.8k from Gloucester center

Parking, Air Conditioner, Child Friendly

4 Bedrooms8 Guests
New to Booking
$535
Average price / night
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Painter's Perch: Rocky Neck
Painter's Perch: Rocky Neck
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms5 Guests
New to Booking
$722
Average price / night
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CbytheSea - Ocean View Penthouse
CbytheSea - Ocean View Penthouse
Apartment
Gloucester, MA, USA
0.8k from Gloucester center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

1 Bedroom4 Guests
9.5

Superb

39 reviews

$507
Average price / night
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Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries
Rocky Neck waterfront 2 bed 2 bath apt walk to the beach, restaurants, galleries
Apartment
Gloucester, MA, 01930, United States
0.7k from Gloucester center

AC, Crib, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

4 reviews

$377
Average price / night
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Beau's Beach House
Beau's Beach House
House
Gloucester, MA, USA
1.4k from Gloucester center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
8.4

Very Good

6 reviews

$328
Average price / night
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Fish & Ships on Waterway: Steps to Ocean, Beach, Boulevard, Park, Restaurants
Fish & Ships on Waterway: Steps to Ocean, Beach, Boulevard, Park, Restaurants
Apartment
Gloucester, MA, 01930, United States
0.7k from Gloucester center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$290
Average price / night
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Waterfront charming home in RockyNeck,Gloucester   4-bedroom
Waterfront charming home in RockyNeck,Gloucester 4-bedroom
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Toys

4 Bedrooms7 Guests
New to Booking
$1268
Average price / night
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Single Level Home - Steps to Downtown Gloucester & A/C throughout
Single Level Home - Steps to Downtown Gloucester & A/C throughout
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

47 reviews

$290
Average price / night
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Downtown Dahlias fully remodeled in the heart of Gloucester
Downtown Dahlias fully remodeled in the heart of Gloucester
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

AC, Dryer, Elevator, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$482
Average price / night
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Loft Townhouse in Downtown Gloucester #3
Loft Townhouse in Downtown Gloucester #3
House
Gloucester, MA, 01930, United States
0.7k from Gloucester center

Internet, No Smoking

1 Bedroom5 Guests
New to Booking
$413
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Gloucester.

Stay Near Gloucester's Top Attractions

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Gloucester Vacation Rentals on the Map

Frequently Asked Questions

You can explore 388 verified vacation rentals in Gloucester. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Gloucester vary depending on the season, property size, and location. Rates typically start from around $173 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Gloucester include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Gloucester welcome pets. Currently, 24 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Gloucester often include amenities such as Fireplace/Heating, Laundry, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.