Gloucester Vacation Rentals from ￥14,483: Search Short-Term 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 .

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

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Our top choices for Gloucester vacation rentals

A wooden deck with a glass door, a staircase, and outdoor furniture.

1. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

￥100,061 total

includes taxes & fees

Nov 16 - Nov 17

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

2. New England Coastal Residence

Gloucester

Richard B.

￥116,492 total

includes taxes & fees

Nov 16 - Nov 17

A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

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

Gloucester

Maarij K.

￥139,863 total

includes taxes & fees

Nov 16 - Nov 17

A sunset over a beach with trees and a rocky shoreline.

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

Gloucester

Catherine C.

￥32,666 total

includes taxes & fees

Nov 19 - Nov 20

A two-story house with a well-maintained lawn and a wooden fence.

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

East Gloucester

Nina R.

￥129,826 total

includes taxes & fees

Nov 24 - Nov 25

A modern kitchen with white cabinetry, a wooden dining table, and a built-in TV.

6. The Essex of Gloucester

Gloucester

Katie B.

￥32,518 total

includes taxes & fees

Nov 16 - Nov 17

A cozy attic bedroom with wooden walls, a sloped ceiling, and a skylight. There are three beds arranged in a U-shape, a small table, and a bench.

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

Gloucester

Karen T.

￥76,415 total

includes taxes & fees

Nov 30 - Dec 1

A covered deck with white chairs and a bench, overlooking the ocean.

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

Rockport

Emmy D.

A harbor with boats docked, a pier, and houses along the shore.

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

Rockport

Heidi K.

￥39,420 total

includes taxes & fees

Nov 16 - Nov 17

A cozy living room with a fireplace, a dining area, and a kitchen with dark cabinets and a white countertop.

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

Rockport

Dave

￥68,008 total

includes taxes & fees

Dec 1 - Dec 2

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.

￥38,853 total

includes taxes & fees

Nov 18 - Nov 19

A coastal town with a sandy beach, houses, and a clear view of the sea.

12. 2BR Home Minutes to Downtown Rockport+Beach!

Rockport

Janet C.

￥69,675 total

includes taxes & fees

Nov 16 - Nov 17

A coastal town with houses along the shoreline, a beach, and a rocky outcrop.

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

Rockport

Laura W.

￥68,038 total

includes taxes & fees

Nov 16 - Nov 17

A rocky beach with large boulders, a clear blue sky, and houses in the background.

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

Rockport

Dominique

￥52,393 total

includes taxes & fees

Nov 30 - Dec 1

A coastal town with houses along the shoreline, a sandy beach, and a rocky outcrop.

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

Rockport

Maryanne H.

￥78,314 total

includes taxes & fees

Nov 16 - Nov 17

A lakeside patio with Adirondack chairs and a small table, surrounded by lush greenery and a view of the lake.

16. Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

Essex

Theodore H.

￥68,619 total

includes taxes & fees

Nov 18 - Nov 19

A dining table set with white plates, bowls, and glasses, accompanied by a vase of yellow tulips.

17. Charming apt -2 Bedroom -Close to Beach/Sleeps 6

Ipswich

Andra W.

￥39,072 total

includes taxes & fees

Nov 17 - Nov 18

A coastal scene with large rocks in the foreground and a clear blue sky.

18. Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Rockport

Jeanni S.

￥228,038 total

includes taxes & fees

Nov 16 - Nov 17

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

19. Riverview charming apt near beach

Ipswich

Stacia S.

￥39,072 total

includes taxes & fees

Nov 22 - Nov 23

A garden pathway leading to a wooden structure with a metal door, surrounded by dense foliage and stone lion statues.

20. 1880 updated Victorian 1st floor, water views. Book for Salem Christmas Tour!

Salem

Gregory

￥38,891 total

includes taxes & fees

Dec 2 - Dec 3

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Find vacation rentals that suit your style

Top Gloucester Hotel Reviews

A large hotel with multiple floors and a beach view.

Beauport Hotel Gloucester

Downtown Gloucester

10/10 Excellent

Kim

A residential house with a stone pathway leading to the front door, surrounded by lush greenery and flowering plants.

Addison Choate Inn

Rockport

10/10 Excellent

Craig

A backyard with a swimming pool, lounge chairs, and umbrellas.

Harbor Light Inn

Marblehead Historic District

10/10 Excellent

Alison

A coastal beach scene with a large house on a rocky outcrop, a sandy beach with people, and a clear blue sky.

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 two-story house with a central entrance, a large arched window, and a wooden door.

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

The Cabot Lodge

Beverly

10/10 Excellent

Bruce

The Courier Hotel

Downtown Salem

10/10 Excellent

Nathan

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 hallway with black doors numbered 2 and 3, a wooden floor, and a large black rug.

The Coach House

Salem

10/10 Excellent

Samuel

A bed in a room with a forest theme, including artificial trees and foliage.

The Cove At Salem

Salem

10/10 Excellent

Emily

Salem Waterfront Hotel & Suites

Salem

10/10 Excellent

Myra

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 hotel room with a large bed, a television, a desk with a lamp, and a view of the ocean.

Ocean House Hotel at Bass Rocks

East Gloucester

10/10 Excellent

Norwich

A modern interior with a staircase, hexagonal patterned floor, and a seating area with blue stools.

The Hotel Salem

Downtown Salem

10/10 Excellent

Tracy

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

Find out more about Gloucester

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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.

Gloucester Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gloucester vacation rentals

1. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

2. New England Coastal Residence

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

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

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

6. The Essex of Gloucester

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

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

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

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

11. Harborside Oasis ★ Harbor View ★ Heart of Downtown

12. 2BR Home Minutes to Downtown Rockport+Beach!

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

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

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

16. Spacious Lakefront Escape w/ 3 Baths + Bonus Bed

17. Charming apt -2 Bedroom -Close to Beach/Sleeps 6

18. Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

19. Riverview charming apt near beach

20. 1880 updated Victorian 1st floor, water views. Book for Salem Christmas Tour!

Find vacation rentals that suit your style

Top Gloucester Hotel Reviews

Beauport Hotel Gloucester

10/10 Excellent

Find out more about Gloucester

Frequently Asked Questions

Can I find a vacation rental in Gloucester?

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

How many vacation rentals are there in Gloucester?

What can I see and do in Gloucester?

What are vacation rentals like in Gloucester?