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

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 NH
The price is AU$935 per night from 5 Jan to 6 Jan
AU$935
5 Jan - 6 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Hampton, within a 10-minute walk of Hampton Beach and Ocean Gaming Casino.
Opens in a new windowPremier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Charming private townhouse-style lodging, a block from Marblehead Harbor

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead MA
A stay at this vacation home places you in the heart of Marblehead, within a 5-minute drive of Marblehead Museum & Historical Society and Massachusetts Bay.
Opens in a new windowCharming private townhouse-style lodging, a block from Marblehead Harbor
Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location

Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location

Newbury MA
When you a stay at this vacation home in Newbury, you'll be on a river, within a 5-minute walk of Newbury Beach and Parker River National Wildlife Refuge.
Opens in a new windowBeautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location
Save an average of 15% on thousands of hotels when you're signed in
Delightful 4-bedroom,  3 bath house all on one floor with in charming Essex

Delightful 4-bedroom, 3 bath house all on one floor with in charming Essex

Essex MA
With a stay at this vacation home, you'll be centrally located in Essex, just a 4-minute walk from Essex River and 9 minutes by foot from Essex Shipbuilding ...
Opens in a new windowDelightful 4-bedroom, 3 bath house all on one floor with in charming Essex
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem MA
A stay at this vacation home places you in the heart of Salem, within a 15-minute walk of Witch House and Witch Dungeon Museum.
Opens in a new windowLeslie's Retreat: Spacious home ideally located to everything
2 Bed/2 Bath Private Beach House One Block from the ocean.

2 Bed/2 Bath Private Beach House One Block from the ocean.

Hampton NH
With a stay at this vacation home in Hampton (Hampton Beach), you'll be steps from Hampton Beach and 4 minutes by foot from Ocean Gaming Casino.
Opens in a new window2 Bed/2 Bath Private Beach House One Block from the ocean.
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Rockport MA
A stay at this vacation home places you in the heart of Rockport, within a 10-minute walk of Back Beach and Front Beach.
Opens in a new windowClassic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.
Featured on HGTV's Beach Hunters

Featured on HGTV's Beach Hunters

Rockport MA
When you stay at this vacation home in Rockport, you'll be on the beach, within a 5-minute drive of Halibut Point State Park and Back Beach.
Opens in a new windowFeatured on HGTV's Beach Hunters
Beautifully renovated home walk to boulevard, town & train

Beautifully renovated home walk to boulevard, town & train

Gloucester MA
Located in Gloucester, this vacation home is by the sea, within a 15-minute walk of Gloucester Unitarian Universalist Church and Fishermen's Memorial ...
Opens in a new windowBeautifully renovated home walk to boulevard, town & train
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
125 Holiday Homes
Lowest Price
AU$935
Highest Price
AU$935
Popular accommodation
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Charming private townhouse-style lodging, a block from Marblehead Harbor, Beautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location, Delightful 4-bedroom, 3 bath house all on one floor with in charming Essex, Leslie's Retreat: Spacious home ideally located to everything, 2 Bed/2 Bath Private Beach House One Block from the ocean., Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops., Featured on HGTV's Beach Hunters, Beautifully renovated home walk to boulevard, town & train

Top trending hotels in Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street Gloucester MA
With a stay at Beauport Hotel Gloucester in Gloucester (Downtown Gloucester), you'll be a 3-minute walk from Massachusetts Bay and 5 minutes by foot from Pavilion ...
Opens in a new windowBeauport Hotel Gloucester
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
Located in Gloucester, Castle Manor Inn is by the ocean, within a 5-minute drive of Stage Fort Park and Fishermen's Memorial Monument.
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
With a stay at Ocean House Hotel at Bass Rocks in Gloucester (East Gloucester), you'll be within a 5-minute drive of Good Harbor Beach and Maritime ...
Opens in a new windowOcean House Hotel at Bass Rocks
Save an average of 15% on thousands of hotels when you're signed in
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue Gloucester MA
Fully refundableReserve now, pay when you stay
Located in Gloucester, The Hotel at Cape Ann Marina is a 4-minute drive from Hammond Castle and 10 minutes from Wingaersheek Beach.
Opens in a new windowThe Hotel at Cape Ann Marina
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.