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
$1,513.00
from $1,513.00 / night
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 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
- 3 nights min
- Child friendly
$895.00
from $895.00 / 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
$896.00
from $896.00 / 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
$1,437.00
from $1,437.00 / 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
$1,262.00
from $1,262.00 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 7 7
- 3 nights min
- Child friendly
$896.00
from $896.00 / 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
$543.00
from $543.00 / night
Magnolia Tides: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Child friendly
- Air conditioning
$1,344.00
from $1,344.00 / 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
$442.00
from $442.00 / 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
$764.00
from $764.00 / 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
$696.00
from $696.00 / 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
$867.00
from $867.00 / 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
$748.00
from $748.00 / night
Bell View: Private tennis court and an in-law suite.
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- sleeps 16 16
- 7 nights min
- Child friendly
- Air conditioning
$1,217.00
from $1,217.00 / 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
$595.00
from $595.00 / 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
$639.00
from $639.00 / 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
$483.00
from $483.00 / 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
$441.00
from $441.00 / 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
$714.00
from $714.00 / 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
$777.00
from $777.00 / 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
$1,020.00
from $1,020.00 / 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
$1,286.00
from $1,286.00 / night
Terra Nova Cottage
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 6 nights min
- Child friendly
- Air conditioning
$650.00
from $650.00 / 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
$1,202.00
from $1,202.00 / 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
$471.00
from $471.00 / 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
$705.00
from $705.00 / 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
$528.00
from $528.00 / 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
$932.00
from $932.00 / night
Bray Cottage: A charming cottage close to Wingaersheek Beach.
Gloucester Cottage
- 3 bedrooms 3
- 1 bathroom
- sleeps 5 5
- 31 nights min
- Ask about children
- Pet friendly
$276.00
from $276.00 / 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
$647.00
from $647.00 / night
Your search has been expanded 5.1 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
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
$545.00
from $545.00 / night
The Lady Bug House
Rockport House - 4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
- Pet friendly
$536.00
from $536.00 / 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
$643.00
from $643.00 / 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
$492.00
from $492.00 / night
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
- 3 nights min
- Child friendly
$1,379.00
from $1,379.00 / night
A sunny and charming 2-bedroom beach retreat close to Rockport's Front Beach.
Rockport House - 3.8 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Ask about children
$483.00
from $483.00 / 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
$640.00
from $640.00 / 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
$417.00
from $417.00 / night
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