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Holiday rentals in Gloucester, Massachusetts

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Travel insights for holiday rentals in Gloucester

Use these up-to-date, data-driven insights about booking a holiday rental in Gloucester including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Gloucester?

The cheapest month to book a vacation rental in Gloucester is January ($462). Conversely, the most expensive month to stay in Gloucester is October ($1,563).

What is the cheapest day to stay in a vacation rental in Gloucester?

The cheapest day to stay in Gloucester is Thursday ($489). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $2,482.

How far ahead should you book a vacation rental in Gloucester?

Save money by booking a vacation rental at least 13 days before your trip to Gloucester. The lowest price found when booking 13 days ahead was $233 per night.
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Other accommodations in Gloucester, MA

Find the perfect holiday rental for your stay in Gloucester, MA. There are 219 hotels in Gloucester, MA and price data was last updated on 9 June 2025. The average price for a hotel in Gloucester, MA is $593/night.
Show all 219 stays
The Hotel at Cape Ann Marina
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

75 Essex Avenue, Gloucester, MA, United States
1.6 km from city centre
Pool
Free Wi-Fi
Parking
$344
Avg. per night
View Deal
Captain's Lodge Motel
Captain's Lodge Motel

Captain's Lodge Motel

237 Eastern Avenue, Gloucester, MA, United States
2.5 km from city centre
Free Wi-Fi
Parking
$226
Avg. per night
View Deal
The Vista
The Vista

The Vista

22 Thatcher Road, Gloucester, MA, United States
2.0 km from city centre
Free Wi-Fi
Parking
$289
Avg. per night
View Deal
Sea Lion Motel
Sea Lion Motel

Sea Lion Motel

138 Eastern Avenue, Gloucester, MA, United States
2.1 km from city centre
Free Wi-Fi
Parking
$321
Avg. per night
View Deal
Elegant Gloucester Beach Getaway with Ocean Views!
Elegant Gloucester Beach Getaway with Ocean Views!

Elegant Gloucester Beach Getaway with Ocean Views!

Gloucester, MA, United States
4.8 km from city centre
Air conditioning
$2,012
Avg. per night
View Deal
Harborview Inn
Harborview Inn

Harborview Inn

71 Western Avenue, Gloucester, MA, United States
1.0 km from city centre
Free Wi-Fi
Air conditioning
$351
Avg. per night
View Deal

Where to stay in Gloucester, MA

Explore different neighbourhoods and areas within Gloucester to find the perfect location for your stay. Map data was last updated on 9 June 2025.
Utilise the map to find properties close to the Gloucester area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

Facts about staying in Gloucester, MA

Find useful tips and insights about staying in Gloucester to help you make the most of your experience. FAQs were last updated on 9 June 2025.

  • How much does a holiday rental in Gloucester cost?

    $593/night is a typical cost for a holiday rental in Gloucester throughout the year. Rental prices do vary though, and you’ll find that May is the most expensive month to book, and January is the cheapest month to book. HotelsCombined users recently found Gloucester holiday rentals for as low as $247/night. In general, any Gloucester rental for $495 or less is a good deal.

  • Are there any Motel holiday rentals in Gloucester?

    At the moment, there are 6 properties listed as a Motel holiday rental in Gloucester. A popular Motel in Gloucester amongst our users is The Vista.

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