Vacation Rentals & Houses in Gloucester

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201 houses

26

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

Cape Ann / Gloucester

Gloucester house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children

Price per night from

$328

Price per night from

$328

(6) Excellent 

14

Waterfront 2 Bedroom !

Cape Ann / Gloucester

Gloucester apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$172

Price per night from

$172

28

Golden Sands at Good Harbor: Across the street from the beach

Cape Ann / Gloucester

Gloucester cottage

7 12 min stay varies

  • 7 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children

Price per night from

$1,013

Price per night from

$1,013

(1) Excellent 

24

Lovely 'Blue Heron Cottage' on Annisquam River!

Cape Ann / Gloucester

Gloucester cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$228

Responds fast!
avg. 22 minutes

Price per night from

$228

(2) Very Good 

18

At the Footbridge entrance to Good Harbor Beach

Cape Ann / Gloucester

Gloucester house

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Private garden

Price per night from

$654

Price per night from

$654

33

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

Cape Ann / Gloucester

Gloucester house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$453

Price per night from

$453

(1) Excellent 

12

Waterfront Woodsy 3BR Cottage

Cape Ann / Gloucester

Gloucester house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$212

Price per night from

$212

(2) Very Good 

12

Vintage Home directly on the Annisquam River

Cape Ann / Gloucester

Gloucester house

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask about pets

Price per night from

$358

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$358

7

Fabulous Waterfront 2 Bedroom - Boat dock option

Cape Ann / Gloucester

Gloucester apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about pets

Price per night from

$77

Price per night from

$77

39

Stunning Views - Spacious Home

Cape Ann / Gloucester

Gloucester house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi

Price per night from

$571

Price per night from

$571

31

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Cape Ann / Gloucester

Gloucester house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$420

Price per night from

$420

31

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

Cape Ann / Gloucester

Gloucester house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children

Price per night from

$477

Price per night from

$477

26

Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach

Cape Ann / Gloucester

Gloucester house

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Ask about children

Price per night from

$1,034

Price per night from

$1,034

18

Waterfront Vacation House w/ Dock

Cape Ann / Gloucester

Gloucester house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$342

Responds fast!
avg. 1 hour 7 minutes

Price per night from

$342

20

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

Cape Ann / Gloucester

Gloucester apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children

Price per night from

$199

Price per night from

$199

(3) Very Good 

26

Bohemia RETREAT Studio

Cape Ann / Gloucester

Gloucester apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Private garden

Price per night from

$132

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$132

25

Seaside House: Good Harbor Beach and the Back Shore right outside

Cape Ann / Gloucester

Gloucester house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children

Price per night from

$634

Price per night from

$634

40

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Cape Ann / Gloucester

Gloucester house

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Ask about children

Price per night from

$703

Price per night from

$703

11

Cozy Guest Studio

Cape Ann / Gloucester

Gloucester studio

Studio 2 3 nights min

  • Studio
  • sleeps 2
  • 3 nights min

Price per night from

$189

Price per night from

$189

(10) Excellent 

40

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

Cape Ann / Gloucester

Gloucester apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$137

Price per night from

$137

29

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

Cape Ann / Gloucester

Gloucester cottage

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children

Price per night from

$306

Price per night from

$306

19

Salt Island Views: Walking distance to Good Harbor & Long Beach.

Cape Ann / Gloucester

Gloucester house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children

Price per night from

$506

Price per night from

$506

23

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Cape Ann / Gloucester

Gloucester house

4 7 3 nights min

  • 4 bedrooms
  • sleeps 7
  • 3 nights min
  • Ask about children

Price per night from

$653

Price per night from

$653

(1) Excellent 

12

Close to Half Moon Bay

Cape Ann / Gloucester

Gloucester apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 1 mi

Price per night from

$143

Price per night from

$143

(1) Average 

24

Captain John Stephens House: Sparkling new studio in the heart of Gloucester

Cape Ann / Gloucester

Gloucester studio

Studio 2 7 nights min

  • Studio
  • sleeps 2
  • 7 nights min
  • Ask about children

Price per night from

$91

Price per night from

$91

11

Stage Fort Park Place

Cape Ann / Gloucester

Gloucester house

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$307

Price per night from

$307

57

Strawberry Cove House: Multi-level waterfront home

Cape Ann / Gloucester

Gloucester house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Ask about children

Price per night from

$943

Price per night from

$943

35

Nature Lover's Paradise .5-1mile to beaches, nature walks, golf, museums, couple

Cape Ann / Gloucester

Gloucester house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$133

Price per night from

$133

23

Sea Fox: Custom-designed home with rights to private Coffins Beach

Cape Ann / Gloucester

Gloucester house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$391

Price per night from

$391

18

Walk to Beach - Modern Apartment

Cape Ann / Gloucester

Gloucester house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$159

Price per night from

$159

11

Good Harbor Escape: Swim or walk over to Good Harbor Beach!

Cape Ann / Gloucester

Gloucester house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children

Price per night from

$353

Price per night from

$353

9

Coastal, Cute & Cozy|Close to Everything

Cape Ann / Gloucester

Gloucester apartment

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Pet Friendly

Price per night from

$126

Price per night from

$126

21

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

Cape Ann / Gloucester

Gloucester house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

23

Eastern Point on the Sea: Water views, private beach and gorgeous sunrises

Cape Ann / Gloucester

Gloucester house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$108

Price per night from

$108

5

Quiet cottage near beach

Cape Ann / Gloucester

Gloucester house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children
  • Pet Friendly
  • Private garden

Price per night from

$195

Responds fast!
avg. 1 hour 27 minutes

Price per night from

$195

20

Long Beach House: Large, comfortable home just 285 feet from the white sands!

Cape Ann / Gloucester

Gloucester house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$377

Price per night from

$377

37

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Cape Ann / Gloucester

Gloucester house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children

Price per night from

$533

Price per night from

$533

27

Family Tides: Only a half-mile from Good Harbor Beach.

Cape Ann / Gloucester

Gloucester house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$434

Price per night from

$434

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.