Gloucester 3-bedroom Apartments, Vacation Rentals & More - 46 Rentals Available.
46 Vacation rentals
Filters applied: 3+ 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
$1,467.00
from $1,467.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$940.00
from $940.00 / 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
$881.00
from $881.00 / 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
- 3 nights min
- Child friendly
$1,349.00
from $1,349.00 / 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
$1,237.00
from $1,237.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$831.00
from $831.00 / night
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
$545.00
from $545.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$1,323.00
from $1,323.00 / 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
$742.00
from $742.00 / 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
$842.00
from $842.00 / night
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Ask about children
- Pet friendly
$734.00
from $734.00 / 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
- Air conditioning
$1,449.00
from $1,449.00 / 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
$586.00
from $586.00 / 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
$622.00
from $622.00 / 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
$476.00
from $476.00 / 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
$701.00
from $701.00 / night
Plaisance - a summer vacation rental near Bass Rocks
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$755.00
from $755.00 / 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
$1,001.00
from $1,001.00 / 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
$1,262.00
from $1,262.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Child friendly
- Air conditioning
$631.00
from $631.00 / 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
$1,179.00
from $1,179.00 / 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
- Pet friendly
$685.00
from $685.00 / 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
$531.00
from $531.00 / 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
$914.00
from $914.00 / 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
$480.00
from $480.00 / 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
$635.00
from $635.00 / night
Your search has been expanded 12.9 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
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$516.00
from $516.00 / night
Booth Cottage: Walk down a private path to fabled Singing Beach.
Manchester-by-the-Sea House - 5.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 6 nights min
- Ask about children
- Pet friendly
$877.00
from $877.00 / night
Four Winds: A serene escape close to picturesque Rockport village.
Rockport House - 3.6 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$379.00
from $379.00 / night
The Robert House: 4 bedroom Rockport village house, sleeps 7
Rockport House - 3.9 miles away
- 4 bedrooms 4
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Child friendly
$532.00
from $532.00 / night
Beautiful oceanfront home with sweeping water views and private beach.
Rockport House - 3.8 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 10 10
- 3 nights min
- Child friendly
$2,043.00
from $2,043.00 / night
Granite Pier: Blends traditional craftsmanship with modern amenities. Views!
Rockport House - 4.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
- Air conditioning
$843.00
from $843.00 / 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
$2,129.00
from $2,129.00 / 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
$742.00
from $742.00 / night
Ryal Side Hideaway Cove: A hidden gem with river views in Beverly.
Beverly House - 12.9 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
- Pet friendly
$442.00
from $442.00 / night
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Rockport House - 4.8 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
- Pet friendly
$840.00
from $840.00 / night
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
$625.00
from $625.00 / 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
$480.00
from $480.00 / night
Sage Hill: Easy access to both Gloucester & Rockport
Rockport House - 2.6 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
- Air conditioning
- Pet friendly
$633.00
from $633.00 / night
Mill Brook Cottage: Enjoy New England charm in Rockport. Walk to the beach!
Rockport House - 3.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Child friendly
$629.00
from $629.00 / night
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