Compare Gloucester Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Gloucester

Secluded 20 acre 10BR ultra contemporary retreat

At this villa, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Gloucester

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Gloucester

Beauport Hotel Gloucester

55 Commercial Street Gloucester MA

$212 nightly

$236 total

Jan 20 - Jan 21

Total with taxes and fees

9.6/10 Exceptional! (910 reviews)

The Hotel at Cape Ann Marina

75 Essex Avenue Gloucester MA

$215 nightly

$240 total

Jan 11 - Jan 12

Total with taxes and fees

8.4/10 Very Good! (779 reviews)

Luxury 1900's romantic retreat steps from the beach - King Suite!

Gloucester MA

9.6/10 Exceptional! (50 reviews)

Luxury Villas

Book luxury villas in Gloucester
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Gloucester. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Gloucester, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Gloucester
You won’t have a problem finding your own space in Gloucester. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Gloucester on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Gloucester rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!