Gloucester 3-bedroom Apartments, Vacation Rentals & More - 44 Rentals Available.
44 Vacation rentals
Filters applied: 3+ Bedrooms
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$325.00
from $325.00 / night
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- 6 nights min
- Child friendly
- Pet friendly
$469.00
from $469.00 / 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
$823.00
from $823.00 / 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
$531.00
from $531.00 / 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
- Child friendly
$699.00
from $699.00 / 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
$647.00
from $647.00 / 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
$365.00
from $365.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$555.00
from $555.00 / 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
$738.00
from $738.00 / 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
$494.00
from $494.00 / 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
$543.00
from $543.00 / 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
$483.00
from $483.00 / 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
$955.00
from $955.00 / 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
- Child friendly
$412.00
from $412.00 / night
Annisquam Heights: Ocean views & traditional New England charm.
Gloucester House
- 6 bedrooms 6
- 2 bathrooms
- sleeps 14 14
- 3 nights min
- Child friendly
$735.00
from $735.00 / 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
$913.00
from $913.00 / 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
$343.00
from $343.00 / 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
$306.00
from $306.00 / night
River Breezes: Direct riverfront with incredible sunsets
Gloucester Cottage
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$472.00
from $472.00 / 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
$547.00
from $547.00 / night
Kris' Kottage at Long Beach
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 3 nights min
- Ask about children
$317.00
from $317.00 / night
Ships Bell: Water views, fantastic sunsets & a swimming quarry
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$394.00
from $394.00 / 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
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$421.00
from $421.00 / 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
- 3 nights min
- Ask about children
$720.00
from $720.00 / night
Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.
Rockport House - 4.6 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 9 9
- 3 nights min
- Child friendly
- Air conditioning
$662.00
from $662.00 / 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
- 7 nights min
- Child friendly
$352.00
from $352.00 / 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
$340.00
from $340.00 / 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
$1,172.00
from $1,172.00 / 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
- 28 nights min
- Child friendly
- Air conditioning
$213.00
from $213.00 / night
Tuller House, a tranquil retreat on Rockport's "the Avenues."
Rockport House - 5.3 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 3 nights min
- Ask about children
$431.00
from $431.00 / 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
$218.00
from $218.00 / 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
$585.00
from $585.00 / 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
- Air conditioning
$439.00
from $439.00 / night
Afternoon Delight: Toast the beauty of the river from the waterfront deck
Beverly House - 12.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Child friendly
- Air conditioning
$370.00
from $370.00 / 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
$526.00
from $526.00 / 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
$445.00
from $445.00 / 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
- 3 nights min
- Child friendly
- Air conditioning
$491.00
from $491.00 / night
Rockport Beach Escape: Stroll to Old Garden Beach or town.
Rockport House - 4.3 miles away
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 3 nights min
- Child friendly
$810.00
from $810.00 / 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
- Child friendly
- Air conditioning
$699.00
from $699.00 / night
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