A harbor with boats, including a 'Whale Watch' and a 'Wejack' named boat.

Gloucester Vacation Rentals

Q: What are some of the best vacation rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach : This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Gloucester are Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and Single Level Home - Steps to Downtown Gloucester & A/C throughout .

Where to?

Dates

November 2026

December 2026

Check prices for these dates

In two weeks

In two months

In three months

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Our top choices for Gloucester vacation rentals

A modern apartment with a dining area, kitchen, living room, and a large window.

1. Long Beach Suites

East Gloucester

Jessie

A living room with a fireplace, a television mounted on the wall, and a variety of decorative items including plants and a large vase.

2. Charming Retreat

East Gloucester

Margaret

$256 nightly

Nov 14 - Nov 15

Total with taxes and fees

3. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Gloucester

Catherine C.

$183 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with a central island, built-in appliances, and a large window providing natural light.

4. Long Beach Suites: 3 Mins Toes To Sand!

East Gloucester

Margaret O.

A staircase with wooden steps leading to a room with a wooden ceiling.

5. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Gloucester

Karen T.

$359 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern staircase with wooden steps and metal railings, leading to a well-lit interior space.

6. New England Coastal Residence

Gloucester

Richard B.

$658 nightly

Nov 10 - Nov 11

Total with taxes and fees

A residential area with houses, a road, and a body of water in the background.

7. Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester

Maarij K.

$766 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden staircase with a railing leading to a covered deck area.

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

Gloucester

Betty

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

9. The Essex of Gloucester

Gloucester

Katie B.

$245 nightly

Dec 2 - Dec 3

Total with taxes and fees

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

10. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

East Gloucester

Nina R.

$688 nightly

Nov 24 - Nov 25

Total with taxes and fees

A marina with boats docked, a clear sky, and a street with parked cars.

11. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Rockport

Wesley G.

$222 nightly

Nov 9 - Nov 10

Total with taxes and fees

A waterfront property with a dock, houses in the background, and a clear sky.

12. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Rockport

Heidi K.

$216 nightly

Nov 13 - Nov 14

Total with taxes and fees

A kitchen with white cabinets, a stainless steel range hood, and a clock on the wall.

13. 2BR Home Minutes to Downtown Rockport+Beach!

Rockport

Janet C.

$377 nightly

Nov 8 - Nov 9

Total with taxes and fees

A living room with a sofa, a coffee table, a plant, and a view into the kitchen.

14. Fall Asleep to Waves — Steps to Shops & Dining

Rockport

Dominique

$341 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with dark blue cabinets, a white countertop, and a wooden ceiling.

15. The Bookstore · King Beds · Walk to Beach · Private Parking

Rockport

Dave

$379 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

16. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport

Maryanne H.

$425 nightly

Nov 9 - Nov 10

Total with taxes and fees

A bedroom with a bed, a painting, and a view of the outdoors.

17. Balcony • KING Suite • Walk2Beach+Bearskin • Parking

Rockport

Dale k.

$426 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinets, and a large window.

18. NEWLY RENOVATED STUDIO CLOSE TO DOWNTOWN IPSWICH

Ipswich

Dawne

$201 nightly

Nov 22 - Nov 23

Total with taxes and fees

A modern kitchen with stainless steel appliances, light grey cabinets, and a tiled backsplash.

19. Riverview charming apt near beach

Ipswich

DAVID A.

$223 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered outdoor deck with a grill, a table with chairs, and an umbrella.

20. 2b apt loft Downtown Ipswich

Ipswich

Helen M.

$207 nightly

Nov 8 - Nov 9

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Top Gloucester Hotel Reviews

A cozy living room with a sofa, armchair, and a coffee maker on a table.

Addison Choate Inn

Rockport

10/10 Excellent

Craig

A wooden deck with outdoor seating, overlooking a body of water and a rocky shoreline.

Bearskin Neck Motor Lodge

Rockport

10/10 Excellent

Mary Beth

Harbor Light Inn

Marblehead Historic District

10/10 Excellent

Alison

A bedroom with a fireplace, a large bed with green pillows, a sofa, and a painting on the wall.

The Merchant

Downtown Salem

10/10 Excellent

Amy

A living room with a fireplace, a sofa, a dining table with chairs, and a television.

Compass Rose Inn

Newburyport

10/10 Excellent

Darren

A large, white, two-story building with a cylindrical tower, surrounded by well-maintained gardens and outdoor seating.

Briar Barn Inn

Rowley

10/10 Excellent

Great staff, beautiful aesthetic and charming. We happened upon the Briar Barn looking for a quaint place to sleep for the night. This place was beyond our expectations and we are already planning another visit, with friends, to stay and see the sights of the area. We are New Yorkers and were so impressed by they service, the cleanliness, the vibe, the amenities and the space. We will come back and recommend to others.

Anonymous traveler

A hotel room with two beds, a balcony with a view, and a desk with a chair.

The Vista

East Gloucester

10/10 Excellent

I wasn't expecting much when I booked with Vista, but as soon as I got there I was impressed. The staff was friendly and made you feel welcome and took the time to explain everything you needed to know while staying there. Our room was a little dated, but it was spacious, and very clean! I love to travel and I have to say it was one of the cleanest places I've stayed at. When I booked I was concerned about the view I would be getting based off of others reviews...but I was pleasantly surprised...

morgan

A bedroom with a bed, a nightstand, a lamp, a window with blinds, a coat rack, and a bathroom with a glass door.

The Cabot Lodge

Beverly

10/10 Excellent

Bruce

A hotel room with a large window, a bed, a white sink, a mirror, and a potted plant.

The Courier Hotel

Downtown Salem

10/10 Excellent

Joshua

A hallway with a white door, wicker chairs, and a patterned rug.

The Coach House

Salem

10/10 Excellent

Samuel

A bedroom with a large clawfoot bathtub, a four-poster bed, and a wooden ceiling.

Silsbee's by Daniels House

Salem

10/10 Excellent

The Silsbee House was conveniently located to most things we wanted to do in Salem. It was also fantastically clean! We stayed in the Rajah room and it was beautiful. The bed was also very comfortable. I appreciated the attention to detail. I also loved that Beekman 1802 products were in the shower. I have sensitive skin and their products don't irritate me. The only thing that would made it more comfortable would have been a place to put my soap bar in the shower and a place to lay out my...

Melanie

A brick pathway leading to a white entrance gate with a sign reading "ENTRANCE".

Clark Currier Inn

Newburyport

10/10 Excellent

I absolutely LOVED staying here! My room was wonderful. I had THE BEST nights sleep! The bed was awesome. The innkeepers are wonderful and tremendously accommodating. The ‘continental breakfast’ was way more extensive. So very nice. And the location is in the heart of Newburyport, making it easy to walk everywhere. This area is so very lovely and I’m grateful I discovered this Inn! I hope to return again someday! I highly recommend Clark Currier Inn.

WENDY

A hotel room with a large bed, a TV, a desk with a computer, and a window with curtains.

The Rockport House

Rockport

10/10 Excellent

Melissa

A two-story house with a central entrance, multiple windows, and a well-maintained front yard.

Sally Webster Inn

Rockport

10/10 Excellent

Mary

A white robe with a blue trim hanging on a wooden hanger.

Salem Waterfront Hotel & Suites

Salem

10/10 Excellent

Myra

A hotel with outdoor seating, fire pits, and a well-lit facade.

The Cove At Salem

Salem

10/10 Excellent

Emily

Find out more about Gloucester

Everything you need to know about Gloucester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gloucester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $204 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation 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 vacation.

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 vacation rental in Gloucester?

Yes, we offer vacation rentals in Gloucester close to Maritime Gloucester, or you can choose a more remote option if you'd like a relaxing place to 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 vacation rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Gloucester are Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam and Single Level Home - Steps to Downtown Gloucester & A/C throughout .

How many vacation rentals are there in Gloucester?

Expedia has 174 vacation rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Half Moon Beach and Stage Fort Park 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 vacation rentals like in Gloucester?

Vacation rentals are private properties you can stay in for a short or long stay in Gloucester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.

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