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 AU$600
includes taxes & fees
1 July - 2 July
Luxury 1900's romantic retreat steps from the beach - King Suite!

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (69 reviews)
"Location, spacious, clean and neat!"
United States
Henry
The price is AU$518
includes taxes & fees
16 June - 17 June
Long Beach Suites

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (8 reviews)
"Perfect size for two couples! Extremely clean and well stocked!!!!"
United States
Kimberly
The price is AU$452
includes taxes & fees
23 June - 24 June
The Essex of Gloucester

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 AU$609
includes taxes & fees
16 June - 17 June
Long Beach Suites: Ocean Views

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 AU$619
includes taxes & fees
30 June - 1 July
Cozy two bedroom house in the heart of Gloucester

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 AU$550
includes taxes & fees
25 June - 26 June
Ocean Breeze / 8-Minute Walk to Beach

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, (12 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 AU$674
includes taxes & fees
24 June - 25 June
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (46 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is AU$842
includes taxes & fees
25 June - 26 June
Beach Life Bliss - steps to the beach

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"Very nice place I loved it"
United States
Erika G.
The price is AU$657
includes taxes & fees
28 June - 29 June
Quaint Neighborhood / Close to Beaches

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, (12 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is AU$882
includes taxes & fees
14 June - 15 June
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

New England Coastal Residence

New England Coastal Residence
Gloucester
The price is AU$1,188
includes taxes & fees
15 June - 16 June
New England Coastal Residence

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (46 reviews)
"House was wonderful and had everything we needed. Very clean and homey for three couples. Great location. Great contact with the host. "
United States
Monica W.
The price is AU$886
includes taxes & fees
21 June - 22 June
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

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 AU$680
includes taxes & fees
30 June - 1 July
Charming Retreat

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 AU$1,538
includes taxes & fees
16 June - 17 June
Classic Coastal Family Home | Walk to Sea;King Bed

Stay at The Neck

Stay at The Neck
Rocky Neck
10.0 out of 10, Exceptional, (1 review)
"Beautiful home with incredible view! Perfect location!! We would definitely stay here again!"
United States
Chris W.
The price is AU$1,958
includes taxes & fees
30 June - 1 July
Stay at The Neck

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

Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!
East Gloucester
8.8 out of 10, Excellent, (19 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 AU$890
includes taxes & fees
25 June - 26 June
Long Beach Suites: 3 Mins Toes To Sand!

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (206 reviews)
"What a wonderful, clean place to stay. The view was amazing and for our first ever experience in Massachusetts just couldn't have been better!!"
United States
Jamie L.
The price is AU$355
includes taxes & fees
15 June - 16 June
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
10.0 out of 10, Exceptional, (24 reviews)
"good location"
United States
Bruce S.
The price is AU$427
includes taxes & fees
16 June - 17 June
Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (33 reviews)
"This is a really beautiful property that's great for a weekend getaway in an incredible little town!"
United States
Travis G.
The price is AU$418
includes taxes & fees
15 June - 16 June
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
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 favourite 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 depend 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 AU$355 per night. Entering your travel dates in the search wizard might find you 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. 

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?

Beach Life Bliss - steps to the beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Another good choice for your trip to Gloucester is Steps to Wingaersheek's Private 1.5 Mile White Dune Beach.

How many holiday rentals are there in Gloucester?

Expedia has 169 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.