Gloucester 2-bedroom Apartments, Vacation Rentals & More - 59 Rentals Available.
59 Vacation rentals
Filters applied: 2+ Bedrooms
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
$328.00
from $328.00 / night
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
$1,014.00
from $1,014.00 / night
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
- Pet friendly
$454.00
from $454.00 / night
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Pet friendly
$673.00
from $673.00 / night
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Ask about children
$1,113.00
from $1,113.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Ask about children
$233.00
from $233.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
$635.00
from $635.00 / night
Welcome Home: Walk to Gloucester's historic harbor and beaches.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 12 12
- min stay varies
- Ask about children
$548.00
from $548.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- min stay varies
- Ask about children
$483.00
from $483.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
$748.00
from $748.00 / night
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Ask about children
$703.00
from $703.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Ask about children
- Pet friendly
$283.00
from $283.00 / night
Strawberry Cove House: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Ask about children
$943.00
from $943.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Ask about children
$653.00
from $653.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
$533.00
from $533.00 / night
Good Harbor Escape: Swim or walk over to Good Harbor Beach!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Ask about children
$354.00
from $354.00 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$653.00
from $653.00 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
- Pet friendly
$573.00
from $573.00 / night
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Ask about children
- Pet friendly
$873.00
from $873.00 / night
Little Red House: Close to Gloucester's historic Stage Fort Park & beaches
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$278.00
from $278.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Air conditioning
$523.00
from $523.00 / night
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$643.00
from $643.00 / night
On the River: Spectacular views of the Mill River, with access for swimming.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Ask about children
$438.00
from $438.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- min stay varies
- Ask about children
$486.00
from $486.00 / night
High Rock Cottage: Astounding views from every angle!
Gloucester House
- 6 bedrooms 6
- 4 bathrooms
- sleeps 10 10
- 7 nights min
- Ask about children
$1,085.00
from $1,085.00 / night
Cher Ami: West Gloucester condo just 0.3 mi to Cressy's Beach.
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 14 nights min
- Ask about children
$160.00
from $160.00 / night
Windows Of Good Harbor: A charming cottage with views of Good Harbor beach.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Ask about children
- Air conditioning
$503.00
from $503.00 / night
River Breezes: Direct riverfront with incredible sunsets
Gloucester Cottage
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- min stay varies
- Ask about children
$454.00
from $454.00 / night
Wingaersheek Sunrise
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
$563.00
from $563.00 / night
Annisquam Heights: Ocean views & traditional New England charm.
Gloucester House
- 6 bedrooms 6
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Ask about children
$1,014.00
from $1,014.00 / night
$403.00
from $403.00 / night
Your search has been expanded 5.5 miles to include more rentals
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$287.00
from $287.00 / night
Directly on Long Beach Rockport MA
Rockport House - 3.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$426.00
from $426.00 / night
North Seas Cottage: Water views in serene Pigeon Cove
Rockport Cottage - 5.5 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Ask about children
- Pet friendly
$293.00
from $293.00 / night
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Rockport Cottage - 5.1 miles away
- 4 bedrooms 4
- 1 bathroom
- sleeps 7 7
- min stay varies
- Ask about children
- Pet friendly
$313.00
from $313.00 / night
Clamshell Landing: Bring your game to its squash & tennis courts!
Essex House - 5.3 miles away
- 6 bedrooms 6
- 5 bathrooms
- sleeps 14 14
- 3 nights min
- Ask about children
- Air conditioning
$1,313.00
from $1,313.00 / night
Meet Me On South Street: Walk to Rockport's village and beaches.
Rockport Condo - 4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Ask about children
$283.00
from $283.00 / night
Granite Pier: Blends traditional craftsmanship with modern amenities.
Rockport House - 4.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$553.00
from $553.00 / night
Sea Vagabond: Amazing water views & close to Long Beach
Rockport House - 3.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Ask about children
- Pet friendly
$248.00
from $248.00 / night
Sea You on Marmion: A gracious Victorian vacation home, steps from the beach.
Rockport House - 4.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- min stay varies
- Ask about children
- Air conditioning
$683.00
from $683.00 / night
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