Gloucester 2-bedroom Apartments, Vacation Rentals & More - 45 Rentals Available.
45 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
$236.00
from $236.00 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Child friendly
$508.00
from $508.00 / 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
$431.00
from $431.00 / 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
$307.00
from $307.00 / 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
$608.00
from $608.00 / 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
$763.00
from $763.00 / 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
$525.00
from $525.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$473.00
from $473.00 / 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
$308.00
from $308.00 / 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
$198.00
from $198.00 / 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
- Ask about children
- Pet friendly
$477.00
from $477.00 / 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
$376.00
from $376.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 3 nights min
- Ask about children
- Air conditioning
$729.00
from $729.00 / 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
$620.00
from $620.00 / 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
$432.00
from $432.00 / 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
- Child friendly
$370.00
from $370.00 / 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
$1,005.00
from $1,005.00 / 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
$394.00
from $394.00 / 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
$455.00
from $455.00 / 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
$579.00
from $579.00 / 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
$856.00
from $856.00 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- sleeps 7 7
- 3 nights min
- Ask about children
- Pet friendly
$205.00
from $205.00 / 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
- Ask about children
- Air conditioning
$238.00
from $238.00 / 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
$313.00
from $313.00 / night
Your search has been expanded 12.9 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
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$590.00
from $590.00 / 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
- 7 nights min
- Ask about children
- Air conditioning
$249.00
from $249.00 / 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
$221.00
from $221.00 / 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
$333.00
from $333.00 / 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
$202.00
from $202.00 / 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
$398.00
from $398.00 / 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
$643.00
from $643.00 / 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
- Ask about children
$401.00
from $401.00 / night
Seacroft:Classic Victorian home with views of the ocean and twin light houses
Rockport House - 4 miles away
- 7 bedrooms 7
- 2 bathrooms
- sleeps 14 14
- 7 nights min
- Child friendly
$631.00
from $631.00 / 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
$264.00
from $264.00 / 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
$178.00
from $178.00 / 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
$268.00
from $268.00 / 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
$483.00
from $483.00 / 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
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
$325.00
from $325.00 / 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
$188.00
from $188.00 / night
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