Updating...

Enter dates for more accurate prices

Gloucester Rentals

Filter

Gloucester Rentals

About Gloucester

69 houses

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 10

$670

1 / 40

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$148

1 / 14

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 32 minutes

$89

1 / 37

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$197

1 / 20

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / Sleeps 12

Responds fast! avg. 3 hours 18 minutes

$314

1 / 12

Beachmont: Easy access to Stage Fort Park, Beaches, and Downtown Gloucester

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 9

$419

1 / 40

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 13

$429

1 / 17

Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 5

Responds fast! avg. 3 hours 13 minutes

$110

1 / 46

Welcome Home: Walk to Gloucester's historic harbor and beaches.

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 12

$476

1 / 21

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / Sleeps 2

$165

1 / 11

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / Sleeps 11

Responds fast! avg. 3 hours 20 minutes

$500

1 / 7

Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$325

1 / 15

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 6

$530

1 / 40

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 7

$650

1 / 23

Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.

Gloucester house

2 bedrooms / 1 bathroom / Sleeps 4

$159

1 / 17

Wingaersheek beach private side 3 level treetop cottage house w/ 4 bedrooms

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 11 minutes

$300

1 / 23

Inviting apartment with harbor views, fireplace, patio, & gas grill!

Gloucester house

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 40 minutes

$56

1 / 28

Bell View: Private tennis court and an in-law suite

Gloucester house

6 bedrooms / 5 bathrooms / Sleeps 16

$904

1 / 38

Waterfront Vacation House w/ Dock

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 1 hour 55 minutes

$250

1 / 18

Updated 'Blue Heron Cottage' on Annisquam River

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 6

Responds fast! avg. 38 minutes

$199

1 / 24

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / Sleeps 6

“Romantic Summerwind Cottage lives up to its name” We thoroughly enjoyed our stay in "Summerwind". It is a truly beautiful house. Linda and Hank, you did a wonderful job in remodeling and decorating the place. The color scheme and artwork reflect the

Responds fast! avg. 3 hours 4 minutes

$240

1 / 26

Waterfront Woodsy 3BR Cottage

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 6

Responds fast! avg. 3 hours 13 minutes

$186

1 / 12

Little Red House: Close to Gloucester's historic Stage Fort Park & beaches

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 5

$275

1 / 20

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$115

1 / 26

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

Gloucester house

2 bedrooms / 1 bathroom / Sleeps 4

$240

1 / 21

Helena House: European flair, close to Plum Cove Beach.

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 7

$183

1 / 21

Cool Cove: Wingaersheek Beach plus your own private beach & all those views!

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$840

1 / 17

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 10

$419

1 / 31

Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$238

1 / 11

Long Beach Place: Just steps from the white sand & surf.

Gloucester apartment

3 bedrooms / 2 bathrooms / Sleeps 8

$390

1 / 25

Stage Fort Park Place

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 14

$269

1 / 11

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 8

$283

1 / 27

Relax at Rocky Neck Hideaway

Gloucester townhouse

1 bedroom / 1 bathroom / Sleeps 3

$129

1 / 23

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 10

$940

1 / 35

Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$640

1 / 24

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / Sleeps 7

$397

1 / 19

Fabulous Waterfront 2 Bedroom - Boat dock option

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$67

1 / 7

Water's Edge: Direct waterfront on picturesque Goose Cove with dock

Gloucester house

3 bedrooms / 3 bathrooms / Sleeps 8

$450

1 / 33

About Gloucester

×

Located on the northern shores of Massachusetts, the town of Gloucester is a vacation paradise that generations of travelers return to every year. The winding streets of this historic town are lined with quaint shops, interesting museums, charming cafes, and unforgettable seafood restaurants. Come here to experience the beautiful rocky coastlines and soft sand beaches of Massachusetts. Hike the trails and stop at breathtaking overlooks with views of the Atlantic Ocean. Visit historic homes and lighthouses. Spend the afternoon swimming, snorkeling, or relaxing on a pristine beach. And then go home at night to your own private vacation rental and host dinner for your family and friends. Many vacation rentals in Gloucester are less expensive than hotels and offer more space and better amenities. Wake up in the morning and watch the sun rise from the deck of your beach condo or summer house, then head downtown to spend the day exploring and making fun vacation memories.

Here are a few additional suggestions for your trip:

  • Take a brewery tour: Gloucester is the traditional home of several long established breweries and craft distilleries. Taste some of the area's award winning artisanal spirits.
  • Tour Hammond Castle: This extraordinary structure was once the home of John Hays Jr., a wealthy eccentric who amassed an extensive collection of medieval artifacts.
  • Visit the Fisherman's Memorial Monument: This fascinating memorial was built in 1925 to honor all the fishermen who have been lost at sea since the 17th century.
  • Play on the beach: Swim, build a sandcastle, or just relax on Good Harbor Beach or Stage Fort Park and Beach, two of the most popular beach destinations in the area.
  • Visit the Rocky Neck Art Colony: This is the oldest established colony for artists in the United States and has been a destination for art lovers since the 1840s.
  • Visit the Beauport Museum or the Cape Ann Historical Museum: Learn more about the fascinating history of Cape Ann with the changing exhibits of these popular museums.

Gloucester offers an ideal scenic back drop for whatever vacation activities you have in mind. The best way to enjoy it all is with a stay in your own apartment rental or summer condo. Find a luxury vacation rental just a few steps from the beach that offers all the amenities you and your family need. While you're visiting Gloucester, be sure to plan day trips to coastal destinations nearby like Cape Cod and Plymouth.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more