Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

Our top choices for Gloucester holiday rentals

Long Beach Suites

2.0 star property
9.2 out of 10, Wonderful, (44)
"Great location beautiful place "
The price is NZ$655
includes taxes & fees
13 Oct - 14 Oct
Long Beach Suites

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

9.8 out of 10, Exceptional, (37)
"Very peaceful, quiet neighborhood. Very comfortable and clean house with all of the ammenities that we needed! Would stay again"
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

9.4 out of 10, Exceptional, (59)
"Beautiful home, close to the beach. Air conditioning wasn’t great and fridge didn’t get very cold. Enjoyed the deck space "
The price is NZ$2,605
includes taxes & fees
5 Oct - 6 Oct
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

10.0 out of 10, Exceptional, (3)
"It was a beautiful home. Clean, up-to-date, and conveniently located. The host was very attentive and helpful. "
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

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

9.8 out of 10, Exceptional, (20)
"Even better in person, host had great hospitality, very clean, quiet, and lovely place to stay! We loved it!"
The price is NZ$877
includes taxes & fees
26 Sept - 27 Sept
Shore Cottage - Coastal gem, a traveler favorite! Outdoor patio, central AC.

Apartments in Salem

3.0 star property
8.0 out of 10, Very good, (46)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
Apartments in Salem

House near down town Salem

9.6 out of 10, Exceptional, (53)
"The apt was spotlessly clean and comfortable including the bedding. Having the two bedrooms, separate livingroom with the large tv, and the full kitchen with the coffee setup was so nice. We really enjoyed and appreciated your accommodations. "
The price is NZ$1,468
includes taxes & fees
12 Oct - 13 Oct
House near down town Salem

Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!

10.0 out of 10, Exceptional, (23)
"Great location. Easy access. Had a wonde Time"
The price is NZ$566
includes taxes & fees
13 Oct - 14 Oct
Ocean Breeze -Dog Friendly Cottage Steps 2 Beach Sleeps 6 - 100 yards to Beach!

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

9.8 out of 10, Exceptional, (59)
"We stayed for 3 nights and lived the decor, spells u can do and walking distant to Salem where everything is . 5 Stars ."
The price is NZ$3,021
includes taxes & fees
21 Oct - 22 Oct
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Leslie's Retreat: Spacious home ideally located to everything

10.0 out of 10, Exceptional, (243)
"Magnificently well maintained home near everything. Great for a large family vacation. "
Leslie's Retreat: Spacious home ideally located to everything

Ocean views from every window. 5min walk to the quiet end of the beach!

9.6 out of 10, Exceptional, (28)
"Relaxing, and very convenient for an easy access to the beach while being a little away from the strip night life :)"
The price is NZ$459
includes taxes & fees
25 Sept - 26 Sept
Ocean views from every window. 5min walk to the quiet end of the beach!

7 Beachside Inn

3.0 star property
8.4 out of 10, Very good, (12)
"Unit was in good order... Wifi was intermittent and dropped regularly, however, privacy, and the in ground pool amenity was a win win. "
The price is NZ$537
includes taxes & fees
25 Sept - 26 Sept
7 Beachside Inn

Salem Haunted Happenings Retreat

9.2 out of 10, Wonderful, (9)
"I had a great stay. The property was clean, well kept, the owners were communitive and answered any of my questions quickly. It was Halloween themed which is pretty fun if your visiting to check out the witchcraft museum and the towns history. It's a beautiful walk to downtown/the museums that also passes by a good coffee and donut shop. I highly recommend staying here. "
The price is NZ$551
includes taxes & fees
30 Sept - 1 Oct
Salem Haunted Happenings Retreat

Ocean Air Suites

2.5 star property
9.4 out of 10, Exceptional, (40)
"Great studio efficiency, with all the amenities right in the room, including washer, dryer. View of the ocean from a shared balcony. Excellent view of weekly beach fireworks display. Only suggestion, black out curtains on side facing parking lot and the lot’s lights. Only suggestion "
Ocean Air Suites

RV Camper - Few Min to the Beach -Boston Downtown and Logan Airport With parking

2.0 star property
5.2 out of 10, (5)
"It was just what we needed. We were in town for 2 concerts and needed a place to sleep and get ready for the shows. Comfy beds."
RV Camper - Few Min to the Beach -Boston Downtown and Logan Airport With parking

Quiet neighborhood and Walking destination to Downtown Salem

9.2 out of 10, Wonderful, (15)
"The area was beautiful and could walk to main Salem restaurants and shops . House was beautiful, clean and has all needed to just stay in and watch a movie and relax!!! Wou oh d stay here again!❤️"
Quiet neighborhood and Walking destination to Downtown Salem

Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

9.6 out of 10, Exceptional, (139)
"Such a beautiful home! Perfect size for my large family and in the perfect walking distance to everything we wanted to do! Would absolutely stay again! "
Townhome #2 -3 Bed/2 Bath Beautifully renovated modern apartment w/Waterviews!

Pool & Jacuzzi Escape near Boston, Salem & Marketstreet Lynnfield

The price is NZ$1,197
includes taxes & fees
25 Sept - 26 Sept
Pool & Jacuzzi Escape near Boston, Salem & Marketstreet Lynnfield

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (133)
"We stayed here for four days. It’s very clean nice beautiful place."
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Whole House Steps from Pleasant Pond

9.6 out of 10, Exceptional, (46)
"Beautiful area next to the pond, quiet and peaceful!"
Whole House Steps from Pleasant Pond
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

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$459 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. 

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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This highly rated holiday home rental in Gloucester is located near the beach, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Another good choice for your trip to Gloucester is Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many holiday rentals are there in Gloucester?

Expedia has 154 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.