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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 day to stay in a vacation rental in Gloucester?

The cheapest day to stay in Gloucester is Sunday (S$ 321). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 948.

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Other accommodations in Gloucester, MA

Find the perfect holiday rental for your stay in Gloucester, MA. There are 189 hotels in Gloucester, MA and price data was last updated on 26 January 2026. The average price for a hotel in Gloucester, MA is .
Harborview Inn
Harborview Inn

Harborview Inn

71 Western Avenue, Gloucester, MA, United States
1.0 km from city centre
Free Wi-Fi
Air conditioning
S$ 267
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
Air conditioning
S$ 159
Avg. per night
View Deal
The Vista
The Vista

The Vista

22 Thatcher Road, Gloucester, MA, United States
1.9 km from city centre
Free Wi-Fi
Parking
S$ 302
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
S$ 213
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
S$ 1,437
Avg. per night
View Deal

Where to stay in Gloucester

Explore different neighbourhoods and areas within Gloucester, MA to find the perfect location for your stay. Map data was last updated on 26 January 2026.
Whether you're visiting Gloucester for leisure or business, utilize the map to find vacation rentals close to your ideal location. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

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 26 January 2026.

  • How much does a holiday rental in Gloucester cost?

    On average, it costs S$ 562 per night for a Gloucester holiday rental, but S$ 511 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Gloucester was for S$ 130 per night. If you can, try to avoid booking your rental September (as this is the most expensive month). Booking August (the cheapest month) may end up saving you money.

  • Are there any Motel holiday rentals in Gloucester?

    There are 6 holiday rentals in Gloucester that fall under the Motel category, the most popular is Captain's Lodge Motel.

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