Book Holiday Homes in Gloucester

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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 NZ$1,030 per night from 9 Feb to 10 Feb
NZ$1,030
9 Feb - 10 Feb
includes taxes & fees
Stay at this beach holiday home in Hampton. Enjoy free Wi-Fi, a beach locale and a water park. Our guests praise the helpful staff in their reviews. Popular ...
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
Stay at this holiday home in Marblehead. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Marblehead Museum & Historical Society and Gas ...
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
Stay at this family-friendly holiday home in Newbury. Enjoy a water park, laundry facilities and patios. Popular attractions Newbury Beach and Plum Island Point ...
Opens in a new windowBeautiful Plum Island Escape; Steps from Beach- Coveted Southern Island Location
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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
Stay at this holiday home in Essex. Enjoy free Wi-Fi, laundry facilities and in-room jetted baths. Popular attractions Essex River and Castle Hill on the Crane ...
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
Stay at this golf holiday home in Salem. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Witch Dungeon Museum and Witch House are located ...
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
The price is NZ$676 per night from 28 Feb to 1 Mar
NZ$676
28 Feb - 1 Mar
includes taxes & fees
Stay at this holiday home in Hampton. Enjoy a beach locale, laundry facilities and air conditioning. Popular attractions Hampton Beach and 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
The price is NZ$1,953 per night from 22 Feb to 23 Feb
NZ$1,953
22 Feb - 23 Feb
includes taxes & fees
Stay at this family-friendly holiday home in Rockport. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Back Beach and Front Beach are located ...
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
Stay at this beach holiday home in Rockport. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Halibut Point State Park and Granite Pier are ...
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
Stay at this holiday home in Gloucester. Enjoy a garden, laundry facilities and patios. Popular attractions Fishermen's Memorial Monument and Pavilion Beach ...
Opens in a new windowBeautifully renovated home walk to boulevard, town & train
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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
539 Holiday Homes
Lowest Price
NZ$174
Highest Price
NZ$1,953
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
Stay at this beach hotel in Gloucester. Enjoy free Wi-Fi, a beach locale and a rooftop terrace. Our guests praise the helpful staff and the property condition ...
Opens in a new windowBeauport Hotel Gloucester
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
The price is NZ$399 per night from 9 Feb to 10 Feb
NZ$399
9 Feb - 10 Feb
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free parking, a marina and a 24-hour front desk. Our guests praise the breakfast and the restaurant in their reviews. ...
Opens in a new windowThe Hotel at Cape Ann Marina
Luxury 1900's romantic retreat steps from the beach - King Suite!

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

Gloucester MA
Stay at this cottage in Gloucester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Plum Cove Beach and Halibut Point Reservation are ...
Opens in a new windowLuxury 1900's romantic retreat steps from the beach - King Suite!
Save an average of 15% on thousands of hotels when you're signed in
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd Danvers MA
Fully refundableReserve now, pay when you stay
The price is NZ$174 per night from 22 Feb to 23 Feb
NZ$174
22 Feb - 23 Feb
includes taxes & fees
Stay at this golf hotel in Danvers. Enjoy free parking, 2 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowDoubleTree by Hilton Boston North Shore
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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.