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223 houses
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Cape Ann / Gloucester
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Ask about children
Map
Price per night from
$328
Price per night from
$328
Waterfront 2 Bedroom !
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Map
Price per night from
$183
Price per night from
$183
Golden Sands at Good Harbor: Across the street from the beach
Cape Ann / Gloucester
7 12 min stay varies
- 7 bedrooms
- sleeps 12
- min stay varies
- Ask about children
Map
Price per night from
$868
Price per night from
$868
Lovely 'Blue Heron Cottage' on Annisquam River!
Cape Ann / Gloucester
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$228
Responds fast!
avg. 19 minutes
Price per night from
$228
Waterfront Woodsy 3BR Cottage
Cape Ann / Gloucester
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Nearest beach 2 mi
- Child Friendly
- Pet Friendly
Map
Price per night from
$213
Price per night from
$213
Inviting apartment with harbor views, fireplace, patio, & gas grill!
Cape Ann / Gloucester
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Child Friendly
- Car not necessary
- Air conditioning
Map
Price per night from
$196
Price per night from
$196
At the Footbridge entrance to Good Harbor Beach
Cape Ann / Gloucester
6 12 7 nights min
- 6 bedrooms
- sleeps 12
- 7 nights min
- Nearest beach 0 mi
- Child Friendly
- Private garden
Map
Price per night from
$654
Price per night from
$654
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Cape Ann / Gloucester
3 8 3 nights min
- 3 bedrooms
- sleeps 8
- 3 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Map
Price per night from
$453
Price per night from
$453
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Cape Ann / Gloucester
4 8 3 nights min
- 4 bedrooms
- sleeps 8
- 3 nights min
- Ask about children
Map
Price per night from
$1,513
Price per night from
$1,513
Stunning Views - Spacious Home
Cape Ann / Gloucester
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Nearest beach 0.8 mi
Map
Price per night from
$573
Price per night from
$573
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Cape Ann / Gloucester
3 8 min stay varies
- 3 bedrooms
- sleeps 8
- min stay varies
- Ask about children
Map
Price per night from
$532
Price per night from
$532
Bohemia RETREAT Studio
Cape Ann / Gloucester
1 3 3 nights min
- 1 bedroom
- sleeps 3
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Private garden
Map
Price per night from
$132
Responds fast!
avg. 2 hours 16 minutes
Price per night from
$132
Welcome Home: Walk to Gloucester's historic harbor and beaches.
Cape Ann / Gloucester
5 12 min stay varies
- 5 bedrooms
- sleeps 12
- min stay varies
- Ask about children
Map
Price per night from
$501
Price per night from
$501
Vintage Home directly on the Annisquam River
Cape Ann / Gloucester
6 12 4 nights min
- 6 bedrooms
- sleeps 12
- 4 nights min
- Beach / lakeside relaxation
- Ask about pets
Map
Price per night from
$360
Price per night from
$360
Fabulous Waterfront 2 Bedroom - Boat dock option
Cape Ann / Gloucester
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Ask about pets
Map
Price per night from
$77
Price per night from
$77
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach
Cape Ann / Gloucester
5 9 min stay varies
- 5 bedrooms
- sleeps 9
- min stay varies
- Ask about children
Map
Price per night from
$996
Price per night from
$996
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Cape Ann / Gloucester
3 7 min stay varies
- 3 bedrooms
- sleeps 7
- min stay varies
- Ask about children
Map
Price per night from
$322
Price per night from
$322
Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town
Cape Ann / Gloucester
2 5 min stay varies
- 2 bedrooms
- sleeps 5
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 1 mi
- Child Friendly
Map
Price per night from
$138
Price per night from
$138
Seaside House: Good Harbor Beach and the Back Shore right outside
Cape Ann / Gloucester
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Ask about children
Map
Price per night from
$666
Price per night from
$666
Diamond in the Sky: Upscale townhouse near Good Harbor Beach.
Cape Ann / Gloucester
3 7 3 nights min
- 3 bedrooms
- sleeps 7
- 3 nights min
- Ask about children
- Air conditioning
Map
Price per night from
$588
Price per night from
$588
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Cape Ann / Gloucester
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Ask about children
- Pet Friendly
Map
Price per night from
$442
Price per night from
$442
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Cape Ann / Gloucester
4 7 min stay varies
- 4 bedrooms
- sleeps 7
- min stay varies
- Ask about children
Map
Price per night from
$487
Price per night from
$487
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Ask about children
Map
Price per night from
$208
Price per night from
$208
Cozy Guest Studio
Cape Ann / Gloucester
Studio 2 3 nights min
- Studio
- sleeps 2
- 3 nights min
Map
Price per night from
$189
Price per night from
$189
Waterfront Vacation House w/ Dock
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Map
Price per night from
$344
Responds fast!
avg. 1 hour 26 minutes
Price per night from
$344
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Cape Ann / Gloucester
5 10 3 nights min
- 5 bedrooms
- sleeps 10
- 3 nights min
- Ask about children
Map
Price per night from
$703
Price per night from
$703
Walk to Beach - Modern Apartment
Cape Ann / Gloucester
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$160
Price per night from
$160
Stage Fort Park Place
Cape Ann / Gloucester
5 14 min stay varies
- 5 bedrooms
- sleeps 14
- min stay varies
- Child Friendly
- Air conditioning
Map
Price per night from
$308
Price per night from
$308
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Cape Ann / Gloucester
2 6 3 nights min
- 2 bedrooms
- sleeps 6
- 3 nights min
- Ask about children
Map
Price per night from
$533
Price per night from
$533
Sea Fox: Custom-designed home with rights to private Coffins Beach
Cape Ann / Gloucester
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Ask about children
- Air conditioning
Map
Price per night from
$412
Price per night from
$412
Nature Lover's Paradise .5-1mile to beaches, nature walks, golf, museums, couple
Cape Ann / Gloucester
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$75
Price per night from
$75
Close to Half Moon Bay
Cape Ann / Gloucester
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Nearest beach 1 mi
Map
Price per night from
$142
Price per night from
$142
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Cape Ann / Gloucester
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Ask about children
- Pet Friendly
Map
Price per night from
$218
Price per night from
$218
Strawberry Cove House: Multi-level waterfront home
Cape Ann / Gloucester
4 10 3 nights min
- 4 bedrooms
- sleeps 10
- 3 nights min
- Ask about children
Map
Price per night from
$943
Price per night from
$943
Good Harbor Escape: Swim or walk over to Good Harbor Beach!
Cape Ann / Gloucester
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Ask about children
Map
Price per night from
$353
Price per night from
$353
Coastal, Cute & Cozy|Close to Everything
Cape Ann / Gloucester
1 2 7 nights min
- 1 bedroom
- sleeps 2
- 7 nights min
- Pet Friendly
Map
Price per night from
$126
Price per night from
$126
Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean
Cape Ann / Gloucester
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Child Friendly
- Car not necessary
- Air conditioning
Map
Price per night from
$156
Price per night from
$156
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Cape Ann / Gloucester
5 10 min stay varies
- 5 bedrooms
- sleeps 10
- min stay varies
- Ask about children
- Pet Friendly
Map
Price per night from
$397
Price per night from
$397
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.
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.