Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton Beach Cottage - River/Beach 2 Block Walk

Hampton
Stay at this vacation home in Hampton. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Hampton Beach and Ocean Gaming ...
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 NZ$491 per night from 16 Apr to 17 Apr
NZ$491
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Salem. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Salem Witch Museum and New England Pirate ...
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
Stay at this vacation home in Lynn. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Revere Beach and Salem Witch Museum ...
Entire Home 2BR 2BTH Quite Area with parking
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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
Stay at this vacation home in Rockport. Enjoy a garden, a pool table, and patios. Popular attractions Shalin Liu Performance Center and Front Beach are located ...
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
Stay at this vacation home in Newburyport. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Plum Island Point and Salisbury 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
Book a stay at this golf vacation home in Salem. Enjoy free WiFi, a garden, and concierge services. Popular attractions Salem Witch Museum and Witch Dungeon ...
Leslie's Retreat: Spacious home ideally located to everything
Massachusetts Abode w/ Deck & Grill: Near Beaches!

Massachusetts Abode w/ Deck & Grill: Near Beaches!

Gloucester
Stay at this vacation home in Gloucester. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions 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
Stay at this vacation home in Gloucester. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Schooner Adventure and Bryan Gallery are located ...
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 NZ$985 per night from 8 Apr to 9 Apr
NZ$985
includes taxes & fees
8 Apr - 9 Apr
Stay at this vacation home in Marblehead. Enjoy air conditioning. Popular attractions Salem Witch Museum and Marblehead Light are located nearby.
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
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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
556 Holiday Homes
Lowest Price
NZ$311
Highest Price
NZ$985
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 NZ$459 per night from 6 Apr to 7 Apr
NZ$459
includes taxes & fees
6 Apr - 7 Apr
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 ...
Beauport Hotel Gloucester
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
Stay at this vacation home in Gloucester. Enjoy free WiFi, a garden, and patios. Popular attractions Plum Cove Beach and Halibut Point Reservation are located ...
Beach Life Bliss - steps to the beach
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is NZ$311 per night from 6 Apr to 7 Apr
NZ$311
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Vista
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Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is NZ$390 per night from 16 Apr to 17 Apr
NZ$390
includes taxes & fees
16 Apr - 17 Apr
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. ...
Castle Manor Inn
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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.

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^Subject to availability and chosen travel dates.