Gloucester 2-bedroom Apartments, Vacation Rentals & More - 64 Rentals Available.
64 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
$227.00
from $227.00 / 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
$1,013.00
from $1,013.00 / 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
$328.00
from $328.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 6 nights min
- Ask about children
$471.00
from $471.00 / night
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$1,084.00
from $1,084.00 / 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
$403.00
from $403.00 / 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
$234.00
from $234.00 / 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
$515.00
from $515.00 / 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
$807.00
from $807.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Ask about children
$650.00
from $650.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Ask about children
$291.00
from $291.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Ask about children
$470.00
from $470.00 / 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
$248.00
from $248.00 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
$492.00
from $492.00 / night
Strawberry Cove House: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Ask about children
$629.00
from $629.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
- Pet friendly
$198.00
from $198.00 / night
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Ask about children
- Pet friendly
$618.00
from $618.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
$377.00
from $377.00 / 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
$397.00
from $397.00 / 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
$200.00
from $200.00 / night
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Pet friendly
$442.00
from $442.00 / 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
$370.00
from $370.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
$356.00
from $356.00 / 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
$1,077.00
from $1,077.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 6 nights min
- Ask about children
$393.00
from $393.00 / 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
$574.00
from $574.00 / night
Wingaersheek Sunrise
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
$499.00
from $499.00 / night
Wingaersheek Bound: Walk to Wingaersheek or private Coffins Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 5 5
- 3 nights min
- Ask about children
$313.00
from $313.00 / night
Lobster Cove House: Picturesque views & walk to Lighthouse Beach.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Ask about children
$806.00
from $806.00 / night
Living is easy high atop Rocky Neck!
Gloucester Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Ask about children
$274.00
from $274.00 / night
$284.00
from $284.00 / night
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 6 nights min
- Ask about children
- Air conditioning
$224.00
from $224.00 / night
Your search has been expanded 4.3 miles to include more rentals
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
$350.00
from $350.00 / night
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
Quarry Crest House: Includes swimming rights to Little Parker quarry
Rockport House - 4.3 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Ask about children
$453.00
from $453.00 / 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
$198.00
from $198.00 / night
Poolside Summers: Swim in the private in-ground pool or walk to the beach
Rockport House - 4.1 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 6 nights min
- Swimming pool
- Ask about children
- Air conditioning
$628.00
from $628.00 / night
Arcadia House: Views of Rockport Harbor, fully air conditioned
Rockport House - 4 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Air conditioning
$457.00
from $457.00 / night
Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!
Rockport Cottage - 3.2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
$186.00
from $186.00 / night
Point de Chene: Direct waterfront historic home with incredible views
Rockport House - 3.8 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Ask about children
- Pet friendly
$548.00
from $548.00 / night
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