Gloucester 4+ bedroom Apartments, Vacation Rentals & More - 20 Rentals Available.
20 Vacation rentals
Filters applied: 4+ Bedrooms
Annisquam's Buoy 23: 4BR Waterfront w/Dock
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Beach/lakeside relaxation
- Ask about children
- Air conditioning
$310
from $310 / night
Bell View: Private tennis court and an in-law suite
Gloucester House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Ask about children
- Air conditioning
$960
from $960 / night
Welcome Home: Walk to Gloucester's historic harbor and beaches.
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$520
from $520 / night
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester House
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$538
from $538 / night
Beachmont: Easy access to Stagefort Park, Beaches & Downtown Gloucester
Gloucester House
- 5 bedrooms 5
- 2 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
- Pet friendly
$470
from $470 / night
Golden Sands at Good Harbor: Across the street from the beach
Gloucester Cottage
- 7 bedrooms 7
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
$1000
from $1000 / 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
$700
from $700 / night
Cool Cove: Wingaersheek Beach plus your own private beach & all those views!
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$1275
from $1275 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$910
from $910 / night
Sea Fox: Custom-designed home with rights to private Coffins Beach
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$550
from $550 / night
Barlovento, the Spanish name for windward, is also the name of one of Eastern
Gloucester Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$1195
from $1195 / night
Sand Song: Just 1 block to Good Harbor Beach
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
- Air conditioning
$572
from $572 / night
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester House
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 6 6
- 3 nights min
- Ask about children
$660
from $660 / night
Townhouse by the Sea: Close to the white sands and lively surf of Long Beach.
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Air conditioning
$372
from $372 / night
Seacastle: Pet-friendly! Close to Coffin's Beach & Wingaersheek.
Gloucester House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 8 8
- 7 nights min
- Ask about children
- Pet friendly
$643
from $643 / night
High Rock Cottage: Astounding views from every angle!
Gloucester House
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$1100
from $1100 / night
Wonson Cove House: Rocky Neck, Eastern Point and Beaches
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$646
from $646 / 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
- Min stay varies
- Ask about children
$1100
from $1100 / night
Eastern Point on the Sea: Water views, private beach and gorgeous sunrises
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$840
from $840 / night
Strawberry Cove House: Multi-level waterfront home
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
$750
from $750 / night
Your search has been expanded 4.8 miles to include more rentals
Sage Hill: Easy access to both Gloucester & Rockport
Rockport House - 2.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Pet friendly
$438
from $438 / night
Directly on Long Beach Rockport MA
Rockport House - 3.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 14 14
- Min stay varies
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$250
from $250 / night
Ocean Front Cottage on Scenic Long Beach
Rockport Cottage - 3.3 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 10 10
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Child friendly
$200
from $200 / night
Point de Chene: Direct waterfront historic home with incredible views
Rockport House - 3.8 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
- Pet friendly
$780
from $780 / 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
- Min stay varies
- Ask about children
$300
from $300 / 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
- Min stay varies
- Ask about children
$688
from $688 / night
Breathtaking views will keep you riveted to your lounge chair.
Rockport House - 4 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Air conditioning
$1150
from $1150 / night
Poolside Summers: Swim in the private in-ground pool or walk to the beach
Rockport House - 4.2 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$733
from $733 / night
Jacob Wirth House: Historic elegance in a stunning Conomo point location.
Essex House - 4.2 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$583
from $583 / 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
- Min stay varies
- Ask about children
$440
from $440 / night
Beach Bound: Minutes from Old Garden Beach and downtown Rockport.
Rockport House - 4.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- 3 nights min
- Ask about children
- Air conditioning
- Pet friendly
$640
from $640 / night
Heavenly Breezes: Perched at the edge of the sea. Incredible views!
Rockport House - 4.4 miles away
- 5 bedrooms 5
- 3 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$1180
from $1180 / night
Beachcomber: Walk to Old Garden Beach and the Village of Rockport
Rockport House - 4.4 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$608
from $608 / night
Rockport Beach Escape: Stroll to Old Garden Beach or town.
Rockport House - 4.4 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- 3 nights min
- Ask about children
$800
from $800 / night
Rockport Seaside Retreat: Walk to waterfront, town and beaches.
Rockport House - 4.4 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$396
from $396 / night
Popples Cove House: Private & serene waterfront setting
Rockport House - 4.7 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$667
from $667 / night
Pigeon Cove: Waterfront views & unparalleled sunrises
Rockport House - 4.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$731
from $731 / night
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove
Rockport House - 4.7 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$650
from $650 / night
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Rockport House - 4.7 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$663
from $663 / night
Spindrift: Direct waterfront, central air, and close to the beach
Rockport House - 4.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Air conditioning
$750
from $750 / night
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