Gloucester 2-bedroom Apartments, Vacation Rentals & More - 55 Rentals Available.
55 Vacation rentals
Filters applied: 2+ Bedrooms
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Ask about children
$1,723.00
from $1,723.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 6 nights min
- Ask about children
$361.00
from $361.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 7 nights min
- Child friendly
$620.00
from $620.00 / night
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
$894.00
from $894.00 / night
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,369.00
from $1,369.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$1,021.00
from $1,021.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
$627.00
from $627.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$1,104.00
from $1,104.00 / night
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Pet friendly
$495.00
from $495.00 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
- Pet friendly
$710.00
from $710.00 / night
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$763.00
from $763.00 / night
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$982.00
from $982.00 / 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
$982.00
from $982.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 3 nights min
- Child friendly
$1,694.00
from $1,694.00 / night
Two Beaches: Walk to Long Beach or Good Harbor!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 8 8
- 6 nights min
- Child friendly
$643.00
from $643.00 / night
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Ask about children
- Pet friendly
$668.00
from $668.00 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
$563.00
from $563.00 / night
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Child friendly
- Air conditioning
$497.00
from $497.00 / night
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$814.00
from $814.00 / night
Plaisance - Enjoy the best of Gloucester living.
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$899.00
from $899.00 / night
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
$1,169.00
from $1,169.00 / night
Cedar Ledge Annisquam: Ocean views & traditional New England charm.
Gloucester House
- 6 bedrooms 6
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Child friendly
- Pet friendly
$1,422.00
from $1,422.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Child friendly
- Air conditioning
$610.00
from $610.00 / night
Chester Square: Waterfront home in historic Annisquam Village.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
$1,283.00
from $1,283.00 / night
Cottage at the Cove: A delightful vacation home close to Plum Cove Beach.
Gloucester House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$494.00
from $494.00 / night
The Mount: Walk to Niles Beach & Rocky Neck from this elegant home.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Air conditioning
$739.00
from $739.00 / night
River's Edge: A charming 2BR riverfront home in Gloucester.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 4 4
- 31 nights min
- Ask about children
$243.00
from $243.00 / night
River Watch: Waterfront rental home with views and private dock.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$571.00
from $571.00 / 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
$991.00
from $991.00 / night
Bray Cottage: A charming cottage close to Wingaersheek Beach.
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
- Pet friendly
$524.00
from $524.00 / night
Changes in Latitude: Charming cottage close to Niles Beach and Rocky Neck.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$688.00
from $688.00 / night
Your search has been expanded 5.1 miles to include more rentals
Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean
Rockport House - 4.5 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Ask about children
- Pet friendly
$647.00
from $647.00 / night
The View: A classic New England cottage with panoramic ocean views.
Rockport House - 4.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Pet friendly
$558.00
from $558.00 / night
Pleasant House: Old-world charm w/ modern updates in the heart of the village
Rockport House - 3.9 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 5 nights min
- Child friendly
- Air conditioning
$816.00
from $816.00 / night
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove
Rockport House - 4.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
- Air conditioning
- Pet friendly
$1,232.00
from $1,232.00 / night
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$516.00
from $516.00 / night
Captain John Butman House: Charming historic home in the village of Rockport.
Rockport House - 3.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
$514.00
from $514.00 / night
Captain's Cottage: Traditional setting with a private footbridge to the beach
Rockport House - 3.5 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
$459.00
from $459.00 / night
Historic charm meets contemporary comfort at Pigeon Hill.
Rockport House - 4.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Ask about children
$533.00
from $533.00 / 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
- 3 nights min
- Ask about children
- Pet friendly
$550.00
from $550.00 / night
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