Book Holiday Homes in Gloucester

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

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton
With a stay at this vacation home in Hampton (Hampton Beach), you'll be within a 10-minute walk of Hampton Beach and Ocean Gaming Casino.
Hampton Beach Cottage - River/Beach 2 Block Walk
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

Salem
The price is AU$451 per night from 16 Apr to 17 Apr
AU$451
includes taxes & fees
16 Apr - 17 Apr
This vacation home is in the heart of Salem, within a 5-minute walk of Salem Witch Trials Memorial and Salem Witch Museum.
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Entire Home 2BR 2BTH Quite Area with parking

Entire Home 2BR 2BTH Quite Area with parking

Lynn
Located in Lynn, this vacation home is within a 15-minute drive of Encore Boston Harbor and TD Garden.
Entire Home 2BR 2BTH Quite Area with parking
Save an average of 15% on thousands of hotels when you're signed in
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

Rockport
A stay at this vacation home places you in the heart of Rockport, within a 15-minute walk of Shalin Liu Performance Center and Front Beach.
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi

Newburyport
Located in Newburyport, this vacation home is by the sea, a 5-minute drive from Newbury Beach and 6 minutes from Plum Island Beach.
Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem
With a stay at this vacation home, you'll be centrally located in Salem, within a 5-minute drive of Salem Witch Museum and Witch House.
Leslie's Retreat: Spacious home ideally located to everything
Massachusetts Abode w/ Deck & Grill: Near Beaches!

Massachusetts Abode w/ Deck & Grill: Near Beaches!

Gloucester
With a stay at this vacation home in Gloucester, you'll be within a 5-minute drive of Good Harbor Beach and Schooner Adventure.
Massachusetts Abode w/ Deck & Grill: Near Beaches!
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Gloucester
A stay at this vacation home places you in the heart of Gloucester, within a 15-minute walk of Massachusetts Bay and Good Harbor Beach.
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2 out of 5
Marblehead
The price is AU$945 per night from 8 Apr to 9 Apr
AU$945
includes taxes & fees
8 Apr - 9 Apr
With a stay at this vacation home in Marblehead, you'll be within a 15-minute drive of Salem Witch Museum and Marblehead Light.
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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
555 Holiday Homes
Lowest Price
AU$282
Highest Price
AU$945
Popular accommodation
Hampton Beach Cottage - River/Beach 2 Block Walk, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Entire Home 2BR 2BTH Quite Area with parking, Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck, Plovers Nest: Perfect Couple Retreat: Gas Fireplace, Sunset water views! Smart TVs, Fast WiFi, Leslie's Retreat: Spacious home ideally located to everything, Massachusetts Abode w/ Deck & Grill: Near Beaches!, Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Top trending hotels in Gloucester

Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
The price is AU$354 per night from 13 Apr to 14 Apr
AU$354
includes taxes & fees
13 Apr - 14 Apr
With a stay at Beauport Hotel Gloucester in Gloucester, you'll be on the beach, just a 3-minute walk from Massachusetts Bay and 5 minutes by foot from Pavilion ...
Beauport Hotel Gloucester
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
Located in Gloucester, this vacation home is by the sea, a 3-minute walk from Plum Cove Beach and within a 5-minute drive of Halibut Point State Park.
Beach Life Bliss - steps to the beach
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is AU$282 per night from 1 Apr to 2 Apr
AU$282
includes taxes & fees
1 Apr - 2 Apr
When you stay at The Vista in Gloucester, you'll be by the ocean, within a 5-minute drive of Good Harbor Beach and Schooner Adventure.
The Vista
Save an average of 15% on thousands of hotels when you're signed in
Harborview Inn

Harborview Inn

3.5 out of 5
71 Western Avenue, Gloucester, MA
The price is AU$336 per night from 2 Apr to 3 Apr
AU$336
includes taxes & fees
2 Apr - 3 Apr
With a stay at Harborview Inn in Gloucester, you'll be near the beach, just a 4-minute walk from Fishermen's Memorial Monument and 5 minutes by foot from Pavilion ...
Harborview Inn
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.