Gloucester Holiday Rentals

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Our top choices for Gloucester holiday rentals

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

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed every bit of our stay."
United States
Kathy B.
The price is NZ$633
includes taxes & fees
1 July - 2 July
Luxury 1900's romantic retreat steps from the beach - King Suite!

Long Beach Suites: Ocean Views

Long Beach Suites: Ocean Views
East Gloucester
9.2 out of 10, Wonderful, (22 reviews)
"Loved the stay Very close to beaches, beautiful area. "
United States
Jessica P.
The price is NZ$1,004
includes taxes & fees
14 July - 15 July
Long Beach Suites: Ocean Views

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (71 reviews)
The price is NZ$805
includes taxes & fees
30 June - 1 July
Long Beach Suites

Herringbone Suite at Beacon House

Herringbone Suite at Beacon House
Downtown Gloucester
The price is NZ$561
includes taxes & fees
29 June - 30 June
Herringbone Suite at Beacon House

Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (14 reviews)
"Wonderful spot to stay and would use it again if I visit later."
United States
Shelley S.
The price is NZ$841
includes taxes & fees
24 July - 25 July
Cozy two bedroom house in the heart of Gloucester

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Downtown Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Excellent downtown location! The loft was clean and well stocked. Great communication from the time of booking through check-out. "
United States
Aimee C.
The price is NZ$772
includes taxes & fees
20 July - 21 July
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"A lovely place! Very clean with very comfortable beds! "
United States
Mariyana K.
The price is NZ$850
includes taxes & fees
9 July - 10 July
Quaint Neighborhood / Close to Beaches

Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (14 reviews)
"Lovely home in a great location. Very clean and fit us well. "
United States
Susan A.
Oceanside Village Home~Private Fenced Yard~Reserved Parking

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.
Gloucester
10.0 out of 10, Exceptional, (24 reviews)
"A beautiful cottage with wonderful amenities and host. Couldn’t have asked for a better place to stay!"
United States
Samson L.
The price is NZ$1,147
includes taxes & fees
26 July - 27 July
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (17 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveller
The price is NZ$783
includes taxes & fees
30 June - 1 July
Charming Retreat

Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (19 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
The price is NZ$801
includes taxes & fees
2 July - 3 July
Ocean Breeze / 8-Minute Walk to Beach

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
10.0 out of 10, Exceptional, (13 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is NZ$1,396
includes taxes & fees
20 July - 21 July
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is NZ$1,826
includes taxes & fees
30 June - 1 July
Classic Coastal Family Home | Walk to Sea;King Bed

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!
Gloucester
10.0 out of 10, Exceptional, (15 reviews)
"Wonderful views, great location, easy access to all of Cape Ann."
United States
Stacey W.
The price is NZ$1,403
includes taxes & fees
30 June - 1 July
Lanesville 4BR Fully Renovated Home • Oceanfront Deck w/ Grill+Outdoor Shower!

New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Great space in a newly renovated building - appliances are brand new and everything is fresh and clean"
United States
Steve K.
The price is NZ$1,482
includes taxes & fees
30 June - 1 July
New England Coastal Residence

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (47 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is NZ$1,375
includes taxes & fees
24 July - 25 July
Beach Life Bliss - steps to the beach

Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!
East Gloucester
8.8 out of 10, Excellent, (20 reviews)
"Excellent location. Walkable to Long Beach. Enjoyed daily walks on the beach. Well appointed condo unit. Plenty of towels and kitchen supplies. Two king sized beds was ideal. Would stay here again."
United States
Molly P.
The price is NZ$1,004
includes taxes & fees
8 July - 9 July
Long Beach Suites: 3 Mins Toes To Sand!

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Enjoyable 2-bedroom lower level apartment in charming Lynn

Enjoyable 2-bedroom lower level apartment in charming Lynn
Lynn
9.8 out of 10, Exceptional, (11 reviews)
"Interesting space with great kitchen setup, roomy, private, and reasonably convenient, and host was responsive immediately when there were problems at check-in (broken lock box and open front door upon arrival). However: the floor was very much not clean (as in, our socks were dirty after ten minutes inside without shoes), the thermostat did not work, and there is a pet door to an outside hallway that cannot be shut/locked. (There's also a lot of noise from the facility upstairs during the day,...
United States
Anastasia P.
The price is NZ$394
includes taxes & fees
7 July - 8 July
Enjoyable 2-bedroom lower level apartment in charming Lynn

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!

Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
3.0 star property
Lynn
The price is NZ$730
includes taxes & fees
29 June - 30 June
Apt in Historic Lynn Neighborhood: 2 Mi to Beach!
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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Top Gloucester Hotel Reviews

Find out more about Gloucester

Everything you need to know about Gloucester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Gloucester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Gloucester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Gloucester holiday rentals we have selected for you start as low as NZ$394 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, there are holiday rentals in Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the scenic seaside and waterfront in Gloucester. Make sure you have time to check out the seafood restaurants and monuments during your trip.

What are some of the best holiday rentals that Gloucester has to offer?

Classic Coastal Family Home | Walk to Sea;King Bed: This highly rated holiday home rental in Gloucester offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Some other top choices in Gloucester are Lovely 'The Buoys Cottage' on Annisquam River! and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many holiday rentals are there in Gloucester?

Expedia has 167 holiday rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Pavilion Beach and Half Moon Beach are a couple of great spots to enjoy the outdoors. Capt Bill & Sons Whale Watch and Cape Ann Museum are other places to visit while you're in town.

What are holiday rentals like in Gloucester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gloucester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.