Book Holiday Homes in Gloucester

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Featured Holiday Homes in Gloucester

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus

*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus

Salem MA
Stay at this beach holiday home in Salem. Enjoy a beach locale, cable/satellite TV service and an in-room coffee maker. Popular attractions Salem Common and ...
Opens in a new window*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus
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$648 per night from 6 Apr to 7 Apr
NZ$648
6 Apr - 7 Apr
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.
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester MA
Stay at this beach holiday home in Gloucester. Enjoy free Wi-Fi, a beach locale and tennis courts. Popular attractions Stage Fort Park and Half Moon Beach are ...
Opens in a new window3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
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3BR Salem Townhouse Minutes to downtown

3BR Salem Townhouse Minutes to downtown

Salem MA
Stay at this holiday home in Salem. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Glendale Cove Beach and Salem Pioneer ...
Opens in a new window3BR Salem Townhouse Minutes to downtown
Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport

Newburyport MA
Stay at this golf holiday home in Newburyport. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Historical Society of Old Newbury and Sisters ...
Opens in a new windowBeautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport
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
Stay at this beach holiday home in Hampton. Enjoy free Wi-Fi, a beach locale and a garden. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowPremier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Rockport MA
Stay at this beach holiday home in Rockport. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Long Beach and Cape Hedge Beach are ...
Opens in a new windowOceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
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 MA
Stay at this holiday home in Salem. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions New England Pirate Museum and Salem ...
Opens in a new windowPrime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Stunning Beach Cottage just steps from Marblehead Harbor and Town

Stunning Beach Cottage just steps from Marblehead Harbor and Town

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 King ...
Opens in a new windowStunning Beach Cottage just steps from Marblehead Harbor and Town
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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$348
Highest Price
NZ$648
Popular accommodation
*Salem Spooky 2BR Downtown| Halloween+Hocus Pocus, 2 Bed/2 Bath Private Beach House One Block from the ocean., 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8, 3BR Salem Townhouse Minutes to downtown, Beautiful 4 Bedroom Home in the Heart of Historic Downtown Newburyport, Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!, Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Stunning Beach Cottage just steps from Marblehead Harbor and Town

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$436 per night from 31 Mar to 1 Apr
NZ$436
31 Mar - 1 Apr
includes taxes & fees
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
Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue Gloucester MA
The price is NZ$348 per night from 18 Apr to 19 Apr
NZ$348
18 Apr - 19 Apr
includes taxes & fees
Stay at this hotel in Gloucester. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowCastle Manor Inn
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$418 per night from 1 Apr to 2 Apr
NZ$418
1 Apr - 2 Apr
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
Save an average of 15% on thousands of hotels when you're signed in
Long Beach Suites

Long Beach Suites

2 out of 5
28 Rockport Rd Gloucester MA
Stay at this aparthotel in Gloucester. Enjoy free Wi-Fi and free parking. Popular attractions Long Beach and Good Harbor Beach are located nearby.
Opens in a new windowLong Beach Suites
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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.

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