Gloucester 3-bedroom Apartments, Vacation Rentals & More - 33 Rentals Available.
33 Vacation rentals
Filters applied: 3+ Bedrooms
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
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
$583
from $583 / 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
Rosemarc House: 180-degree ocean views & a private beach
Gloucester House
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$929
from $929 / night
Water's Edge: Direct waterfront on picturesque Goose Cove with dock
Gloucester House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$450
from $450 / night
River Breezes: Direct riverfront with incredible sunsets
Gloucester Cottage
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$440
from $440 / 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
Long Beach Place: Just steps from the white sand & surf.
Gloucester Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$583
from $583 / 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
Two Beaches: Immaculate single-level 3BR between Long Beach & Good Harbor
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$408
from $408 / night
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester House
- 4 bedrooms 4
- 3 bathrooms
- Sleeps 10 10
- 7 nights min
- Ask about children
$629
from $629 / 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
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
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
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester Cottage
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
$440
from $440 / night
Little Red House: Close to Gloucester's historic Stage Fort Park & beaches
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 5 5
- Min stay varies
- Ask about children
$250
from $250 / night
Victorian House: Explore Rocky Neck's art galleries & restaurants
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$467
from $467 / night
Helena House: European flair, close to Plum Cove Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$320
from $320 / 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
Annie's Place: Sweet cottage just 0.2 miles to Plum Cove Beach
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- Min stay varies
- Ask about children
- Pet friendly
$250
from $250 / 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
Ships Bell: Water views, fantastic sunsets & a swimming quarry
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$458
from $458 / night
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$625
from $625 / 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
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
$372
from $372 / night
Good Harbor Escape: Swim or walk over to Good Harbor Beach!
Gloucester House
- 3 bedrooms 3
- 1 bathroom
- Sleeps 6 6
- 3 nights min
- Ask about children
$380
from $380 / 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
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
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
$633
from $633 / night
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
$310
from $310 / 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
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
Your search has been expanded 21.2 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
Sea Vagabond: Amazing water views & close to Long Beach
Rockport House - 3.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 9 9
- Min stay varies
- Ask about children
- Pet friendly
$235
from $235 / night
Rockport Village House: 3 floors of bright and sunny living space
Rockport House - 3.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$400
from $400 / 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 Cable House: High-end oceanfront family home, 1/10 mi to Cape Hedge Beach
Rockport House - 3.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$850
from $850 / 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
$689
from $689 / night
Forever Views: You'll never want to leave 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
John Oakes Rockport Harbor House: Historical home right on the water
Rockport House - 4.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
$403
from $403 / 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
Annetti's Watch: Ocean views, central A/C & 0.5 mi to beach
Rockport House - 4.2 miles away
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 12 12
- Min stay varies
- Ask about children
- Air conditioning
$640
from $640 / 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
Granite Pier: Blends traditional craftsmanship with modern amenities.
Rockport House - 4.3 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$540
from $540 / 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
$1000
from $1000 / 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
- Pet friendly
$396
from $396 / night
Marmion Way: Rockport's South End. Walk to the beach & into the village.
Rockport House - 4.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Ask about children
- Air conditioning
$425
from $425 / night
Landmark House: Hilltop views of Sandy Bay and the Atlantic Ocean
Rockport House - 4.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- 3 nights min
- Ask about children
$480
from $480 / night
Old Garden Beach House: The ultimate Rockport experience!
Rockport House - 4.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
- Air conditioning
$567
from $567 / 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
$730
from $730 / 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
Clamshell Landing: Bring your game to its squash &tennis courts!
Essex House - 4.9 miles away
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Ask about children
- Air conditioning
$1400
from $1400 / night
Cove View: Sweet cottage across from beautiful Folly Cove
Rockport Cottage - 5 miles away
- 3 bedrooms 3
- 1 bathroom
- Sleeps 5 5
- Min stay varies
- Ask about children
- Pet friendly
$270
from $270 / night
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Rockport Cottage - 5 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 7 7
- Min stay varies
- Ask about children
- Pet friendly
$330
from $330 / night
Mon Altre Cove House: Gather the family to this seaside retreat.
Rockport House - 5.3 miles away
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Pet friendly
$546
from $546 / night
Booth Cottage: Walk down a private path to fabled Singing Beach.
Manchester-by-the-Sea House - 5.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Ask about children
$833
from $833 / night
Afternoon Delight: Toast the beauty of the river from the waterfront deck
Beverly House - 12.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- 7 nights min
- Ask about children
- Air conditioning
$243
from $243 / night
Super Modern European Mansion, 15 min from Boston
Lynnfield Manor house - 17.9 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 11 11
- 30 nights min
- Nearest beach 25 mi
- Swimming pool
- Ask about children
$1100
from $1100 / night
Oceanfront Property - Spectacular Views!!
Salisbury Cottage - 17.9 miles away
- 4 bedrooms 4
- 2 bathrooms
- Sleeps 8 8
- Min stay varies
- Beach/lakeside relaxation
- Ask about children
- Pet friendly
$250
from $250 / night
VILLA RIVIERA on the Merrimack River.
Newburyport Villa - 19.6 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 20 20
- 2 nights min
- Nearest beach 16 mi
- Child friendly
- Air conditioning
$750
from $750 / night
5 MIN WALK to Beach! 3 BDRM COTTAGE Manchester St
Hampton Cottage - 21.2 miles away
- 3 bedrooms 3
- 1 bathroom
- Sleeps 8 8
- Min stay varies
- Child friendly
- Air conditioning
$100
from $100 / night
Renovated 4 Brrm Cottage 1 block to beach!
Hampton House - 21.2 miles away
- 4 bedrooms 4
- 1 bathroom
- Sleeps 10 10
- Min stay varies
- Nearest beach 0 mi
- Child friendly
- Air conditioning
$150
from $150 / night
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