Book Holiday Homes in Gloucester

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Gloucester

Downtown Salem retreat 3BD w/ parking

Downtown Salem retreat 3BD w/ parking

Salem, MA
Stay at this vacation home in Salem. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Salem Witch Museum and Salem Common are ...
Opens in a new windowDowntown Salem retreat 3BD w/ parking
Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC

Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC

Newburyport
Book a stay at this beach vacation home in Newburyport. Enjoy a beach locale, a garden, and kayaking on site. Popular attractions Plum Island Point and Salisbury ...
Opens in a new windowSunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Hampton
The price is NZ$1,086 per night from 6 Nov to 7 Nov
NZ$1,086
6 Nov - 7 Nov
includes taxes & fees
Book a stay at this beach vacation home in Hampton. Enjoy free WiFi, a beach locale, and a water park. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowPremier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Save an average of 15% on thousands of hotels when you're signed in
Coastal Retreat: steps to beach and town

Coastal Retreat: steps to beach and town

Swampscott
Stay at this vacation home in Swampscott. Enjoy laundry facilities and air conditioning. Popular attractions Salem Witch Museum and Revere Beach are located ...
Opens in a new windowCoastal Retreat: steps to beach and town
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem
Book a stay at this golf vacation home in Salem. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Salem Witch Museum and Witch Dungeon ...
Opens in a new windowLeslie's Retreat: Spacious home ideally located to everything
Classic New England Bunkhouse- Home for the whole family!

Classic New England Bunkhouse- Home for the whole family!

Haverhill
The price is NZ$620 per night from 6 Nov to 7 Nov
NZ$620
6 Nov - 7 Nov
includes taxes & fees
Stay at this vacation home in Haverhill. Enjoy air conditioning. Popular attractions Bradford Country Club and Ski Bradford are located nearby.
Opens in a new windowClassic New England Bunkhouse- Home for the whole family!
Delightful 4-bedroom house with AC in charming Essex

Delightful 4-bedroom house with AC in charming Essex

Essex, MA
Stay at this vacation home in Essex. Enjoy laundry facilities, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Wingaersheek Beach and Essex ...
Opens in a new windowDelightful 4-bedroom house with AC in charming Essex
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2 out of 5
Salem
The price is NZ$822 per night from 12 Nov to 13 Nov
NZ$822
12 Nov - 13 Nov
includes taxes & fees
Stay at this vacation home in Salem. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Salem Witch Museum and House of the Seven Gables are ...
Opens in a new windowEntire 4BR 2 Bath Home l Minutes to Downtown Salem
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Gloucester
Stay at this vacation home in Gloucester. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Good Harbor Beach and Cape Ann are located ...
Opens in a new windowCranberry Hill l 9 BR 22 Acre Estate l Sleeps 24
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.

Gloucester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Gloucester vacation homes are the perfect way for you to wing it.

Holiday houses in Gloucester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Gloucester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Gloucester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Gloucester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Gloucester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Gloucester Holiday Homes essential information

Accommodation
558 Holiday Homes
Lowest Price
NZ$303
Highest Price
NZ$1,086
Popular accommodation
Downtown Salem retreat 3BD w/ parking, Sunrise Paradise: 360degree sunset & sunrise views, roof deck, garden dining, grill, AC, Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Coastal Retreat: steps to beach and town, Leslie's Retreat: Spacious home ideally located to everything, Classic New England Bunkhouse- Home for the whole family!, Delightful 4-bedroom house with AC in charming Essex, Entire 4BR 2 Bath Home l Minutes to Downtown Salem, Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Top trending hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is NZ$351 per night from 11 Nov to 12 Nov
NZ$351
11 Nov - 12 Nov
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Opens in a new windowCastle Manor Inn
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
Fully refundableReserve now, pay when you stay
The price is NZ$303 per night from 9 Nov to 10 Nov
NZ$303
9 Nov - 10 Nov
includes taxes & fees
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowOcean House Hotel at Bass Rocks
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
Opens in a new windowBeauport Hotel Gloucester
Save an average of 15% on thousands of hotels when you're signed in
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowSea Lion Motel and Cottages
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.