Gloucester Rentals
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WATERFRONT 1BDRM SPACIOUS STUDIO APARTMENT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come to the Cape named after a Queen NOT an Ugly Fish!! 🤣FABULOUS, quiet, dead end location! Incredible views of the An ...
Click For PricingVRBO
From $595 per night (USD)Expedia
Cozy Beach cottage walkable to Good Harbor and Long Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summer at its best! A delightful spot near the beach, nice private fenced in backyard, walkable to Long Beach and Good H ...
From $595 per night (USD)Expedia
From $457 per night (USD)VRBO
Lovely 'The Buoys Cottage' on Annisquam River!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Walkable Location | Riverside Outdoor Hangout | Eat-In Kitchen Less than 1/2 mile from beaches, parks, and Gloucester f ...
From $457 per night (USD)VRBO
From $1347 per night (USD)Expedia
Elegant Gloucester Beach Getaway with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for ...
From $1347 per night (USD)Expedia
From $662 per night (USD)VRBO
Long Beach Gloucester. 1 minute walk to Beach.Large yard, lush gardens. 1 pup ok
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
"Beachcomber Cottage" is just a few steps to a lovely white sandy beach, (Long Beach) where you will immediately be draw ...
From $662 per night (USD)VRBO
From $478 per night (USD)Expedia
Seaside Escape just steps to Good Harbor beach in Gloucester
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 5
Charming 2 bedroom home located on a quiet Cul de Sac that's just steps to beautiful Good Harbor Beach. Completely renov ...
From $478 per night (USD)Expedia
From $415 per night (USD)VRBO
WALK TO BEACH! Great Location! Booking Sept & Oct! Close to Salem!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Look no further! Enjoy being a guest at this stylish beach bungalow! It is the perfect vacation spot for you and your fa ...
From $415 per night (USD)VRBO
From $319 per night (USD)Expedia
Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
October is coming and that means that Haunted Happenings in Salem, Massachusetts is in full swing. come stay in Gloucest ...
From $319 per night (USD)Expedia
From $440 per night (USD)VRBO
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our idyllic retreat, the ultimate vacation spot for you, your family, and friends. Nestled between the picture ...
From $440 per night (USD)VRBO
From $500 per night (USD)Expedia
Romantic Summerwind Cottage-Harbor View Retreat w/Large Private Deck
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Summerwind Cottage! Wake up to harbor views, enjoy coffee or sunset cocktails on a spacious private deck, and ...
From $500 per night (USD)Expedia
From $440 per night (USD)VRBO
5-star home with quick walk to 2 beaches!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated beach home, steps from two of New England's most beautiful beaches, Good Harbor and Long Beach! This beautifu ...
From $440 per night (USD)VRBO
From $731 per night (USD)Expedia
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Cozy beach cottage located on private white dunes on 1.5 mile Wingaersheek beach. Best of both worlds, large green yard ...
From $731 per night (USD)Expedia
From $700 per night (USD)VRBO
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A quaint 4 bedroom family cottage sits on the edge of the salt marsh and dunes of Good Harbor Beach in Gloucester, Massa ...
From $700 per night (USD)VRBO
From $213 per night (USD)Expedia
Charming Studio, Private Bath, Kitchenette, Deck, Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Large attractive studio, windows with great winter views, leafy vista In the summer. Firm queen-sized bed. Well-equippe ...
From $213 per night (USD)Expedia
From $829 per night (USD)VRBO
Cape Ann, Annisquam panoramic ocean views from every room.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 11
This charming shingled house, built in 1917 and respectfully renovated in recent years, sits atop a rocky hill overlooki ...
From $829 per night (USD)VRBO
From $469 per night (USD)Expedia
Walk to Good Harbor and Long Beach -Vacation Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Walk to two beaches! Spend your day at the beach or relaxing on the porch with a book. 3 Bedrooms, 2 Baths, (Sleeps 6) ...
From $469 per night (USD)Expedia
From $504 per night (USD)VRBO
Clean Waterfront Classic Cottage with Private Beach
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Location x3! This classic, cozy, waterfront cottage that sits on a private beach overlooking the Annisquam River in Glou ...
From $504 per night (USD)VRBO
From $408 per night (USD)Expedia
Quaint Neighborhood / Close to Beaches
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Ideal for up to 5 people, this apartment is located on the second floor of a two-unit building. It has three bedrooms, o ...
From $408 per night (USD)Expedia
From $549 per night (USD)VRBO
Amazing Waterfront/Access 4BDRM in Riggs Point
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Come and relax at our quaint, amazing home fully equipped with everything to make you feel right at home. With spacious ...
From $549 per night (USD)VRBO
From $690 per night (USD)Expedia
Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Vacation time? This beach gem awaits you! Be surrounded by rich history, absolutely gorgeous views, a baseball field, te ...
From $690 per night (USD)Expedia
From $270 per night (USD)VRBO
Massachusetts Abode w/ Deck & Grill: Near Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Take a much-needed break from your day-to-day and book a stay at this 2-bed, 1-bath Gloucester vacation rental! Convenie ...
From $270 per night (USD)VRBO
From $322 per night (USD)Expedia
Blue Magnolia - A quiet apartment in a quaint Gloucester MA village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your cozy getaway awaits in Gloucester at this charming apartment. With 2 bedrooms, including a king bed and a queen bed ...
From $322 per night (USD)Expedia
From $1412 per night (USD)VRBO
Niles Beach House - Beach & Boston Skyline Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Take in the amazing view of Gloucester Harbor and the Boston skyline from this modern, fully air conditioned vacation re ...
From $1412 per night (USD)VRBO
From $369 per night (USD)Expedia
Stroll to SeaView/Beach; Great Yard
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Features ☆ Short walk to breathtaking views of Ipswich Bay ☆ Access to private estate with walking paths that connects ...
From $369 per night (USD)Expedia
From $391 per night (USD)VRBO
Elegant Bayview Victorian Home; walk to beach
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Discover the historic charm of Bayview, a stunning private estate once home to Civil War General Benjamin F. Butler. Spa ...
From $391 per night (USD)VRBO
From $1195 per night (USD)Expedia
Tidebend: River Views and Gracious Comfort
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to Tidebend, your next Gloucester escape! This stunning 6-bedroom, 2.5-bath home overlooks the picturesque Annis ...
From $1195 per night (USD)Expedia
From $499 per night (USD)VRBO
cottage close to long beach and good harbor
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Summer at its best! A delightful spot near the beach with nice private backyard, walkable to Long Beach and Good Harbor ...
From $499 per night (USD)VRBO
From $1340 per night (USD)Expedia
Oceanfront Escape: Beach Access on Private Estate
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 12
Available mid-June thru October Features: ☆ Waterfront home overlooking Ipswich Bay ☆ Patio with breathtaking ocean view ...
From $1340 per night (USD)Expedia
From $663 per night (USD)VRBO
Stay at Good Harbor Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ 3-min ...
From $663 per night (USD)VRBO
From $403 per night (USD)Expedia
Stay at the Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Waterfr ...
From $403 per night (USD)Expedia
From $2769 per night (USD)VRBO
Stay at Good Harbor Beach
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ 4-minu ...
From $2769 per night (USD)VRBO
From $2101 per night (USD)Expedia
Timeless Seaside Estate: 3 Lodgings, Private Beach
- Bedrooms:
- 6
- Bathrooms:
- 9
- Sleeps:
- 19
Features: ☆ The estate has walking paths that connect residents to various estate amenities, including two private beach ...
From $2101 per night (USD)Expedia
From $1014 per night (USD)VRBO
Classic Coastal Family Home | Walk to Sea;King Bed
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to this beautiful historic Gloucester coastal home just steps from the waterfront and minutes from beaches, downt ...
From $1014 per night (USD)VRBO
From $1284 per night (USD)Expedia
Life on Deck - Spacious Coastal Home & Easy Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
New for 2026! Stroll to Long Beach or Good Harbor Beach, or simply relax on the large deck. Nestled between the two beac ...
From $1284 per night (USD)Expedia
From $1018 per night (USD)VRBO
BRAND NEW, Complete renovation: 4-Bedroom, 3.5 Bath, private Annisquam Gem!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to a completely reimagined coastal retreat in the heart of Annisquam, where timeless New England charm meets mod ...
From $1018 per night (USD)VRBO
From $1524 per night (USD)Expedia
NEW 5 BEDROOM-PRIME LOCATION IN GLOUCESTER WITH EVENT SPACE AVAILABLE
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Let us host your Micro-Wedding this summer! PRIME LOCATION IN GLOUCESTER WITH WATER VIEWS & EVENT-FRIENDLY YARD! A 5-bed ...
From $1524 per night (USD)Expedia
From $1567 per night (USD)VRBO
Oceanfront Luxury on Gloucester's Back Shore
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
• Luxury renovated home on Gloucester's iconic Back Shore, sweeping ocean views from almost every room • Oceanfront Prim ...
From $1567 per night (USD)VRBO
From $475 per night (USD)Expedia
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
KEY FEATURES: *4 season sunroom with panoramic ocean views *Primary loft bedroom with ensuite bath and dedicated work sp ...
From $475 per night (USD)Expedia
From $131 per night (USD)VRBO
Gloucester Large 2-Room Studio, Full Kitchen, Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Annisquam River Views | Beach House Feel | 1/4 Mi to Beach & Gloucester Fisherman's Memorial Savor salt air and small-t ...
From $131 per night (USD)VRBO
From $1358 per night (USD)Expedia
Modern oceanfront home with scenic deck, grill, games, chef's kitchen, & W/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Magnificent sunrise views await at this oceanfront charmer! Modernly updated and full of light, the interior of Magnolia ...
From $1358 per night (USD)Expedia
From $422 per night (USD)VRBO
Beautifully renovated home walk to boulevard, town & train
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Visit the charming coastal town of Gloucester, MA, and choose this beautiful home as the perfect retreat for your next v ...
From $422 per night (USD)VRBO
From $384 per night (USD)Expedia
Centrally located open concept apartment with parking, central AC, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located in the charming coastal town of Gloucester, this apartment offers a comfortable and convenient retreat ...
From $384 per night (USD)Expedia
From $1733 per night (USD)VRBO
Private beachfront escape on Coffins Beach w/ amazing views & private beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to your enchanting getaway in Gloucester, MA, where oceanfront luxury meets serene privacy. This inviting abode ...
From $1733 per night (USD)VRBO
From $413 per night (USD)Expedia
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An exceptional stay awaits you and yours at this beautifully updated vacation home in a quiet, highly desirable East Glo ...
From $413 per night (USD)Expedia
From $384 per night (USD)VRBO
Peaceful centrally located home: w/ yard & walking distance to town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Nestled at the end of a quiet dead-end street in Gloucester, MA, this charming house offers a serene retreat with a back ...
From $384 per night (USD)VRBO
From $306 per night (USD)Expedia
Centrally located charmer with expansive patio, board games, & central AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in the heart of Gloucester, Bianca's House offers a pleasant city getaway for you and your loved ones! Entertain ...
From $306 per night (USD)Expedia
From $516 per night (USD)VRBO
Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Perched right on Gloucester Harbor, this large, two-level studio sleeps like a one bedroom, with the entire upper floor ...
From $516 per night (USD)VRBO
From $371 per night (USD)Expedia
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this tranquil Gloucester gem on your next getaway! Nearby, you'll love having easy access to Bass Rocks Golf a ...
From $371 per night (USD)Expedia
From $1305 per night (USD)VRBO
Gull's Nest - Ocean Views from the Living Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perched on a hill overlooking Ipswich Bay, this inviting coastal retreat is the perfect place to slow down and enjoy the ...
From $1305 per night (USD)VRBO
From $588 per night (USD)Expedia
River's Edge Cottage Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This bright and spacious vacation home blends modern comfort with classic New England charm, creating the perfect settin ...
From $588 per night (USD)Expedia
From $304 per night (USD)VRBO
Herringbone Suite at Beacon House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Herringbone Suite at Beacon House is a private 1-king bed, 1-bath guest suite in a historic Queen Anne Victorian on ...
From $304 per night (USD)VRBO
From $619 per night (USD)Expedia
Stay at Wingaersheek
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ 2-minu ...
From $619 per night (USD)Expedia
From $1549 per night (USD)VRBO
Stay at Gloucester Harbor
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ Direct ...
From $1549 per night (USD)VRBO
From $215 per night (USD)Expedia
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Gorgeous view of the Mill River just behind the house. Hiking, boating, marine activities and city life just minutes awa ...
From $215 per night (USD)Expedia
From $1067 per night (USD)VRBO
Beach Bound - Cape Ann Coastal Escape
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
New for 2026! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of modern comfort and coastal ...
From $1067 per night (USD)VRBO
From $915 per night (USD)Expedia
New England Coastal Residence
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious multi-level coastal apartment ideal for families and groups of up to 10 guests. The home features 4 large bedro ...
From $915 per night (USD)Expedia
From $329 per night (USD)VRBO
Cozy Coastal Cape Ann Suite - Near Downtown, Beaches & Dining
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Wake up minutes from the water on Massachusetts' beautiful North Shore. This private, newly renovated 2-bedroom guest su ...
From $329 per night (USD)VRBO
From $582 per night (USD)VRBO
Southwestern Coastal Retreat • Walk to Good Harbor Beach, 3BR Gloucester Getaway
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to your relaxing North Shore escape at 10 Loma Drive in Gloucester, Massachusetts. Just minutes from the soft sa ...
From $582 per night (USD)VRBO
From $246 per night (USD)VRBO
Beautiful cottage on lovingly landscaped property just 5 minute walk to ocean!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful cottage by the sea in Folly Cove! Come and enjoy a relaxing retreat style experience in the historically sign ...
From $246 per night (USD)VRBO
From $859 per night (USD)VRBO
Waterway View; Steps to Ocean, Beach, Blvd, Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Right on the canal where ships and boats pass by all day, and just a hundred yards to see the great ocean view on Stacey ...
From $859 per night (USD)VRBO
From $295 per night (USD)VRBO
Elevated Fish & Ships on Canal: Walk to Beach,Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your charming waterfront retreat in downtown Gloucester at Blynman Canal! This 2-bedroom, 1-bathroom apartmen ...
From $295 per night (USD)VRBO
From $195 per night (USD)VRBO
Cozy Apartment at Green Landing - AC - No Cleaning Fee - Hassle Free Check Out
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We want your departure to feel easy and hassle free without a cleaning fee! Quick Glance: Max Capacity: 2 1 Queen Bed ...
From $195 per night (USD)VRBO
From $748 per night (USD)VRBO
Delightful 3-bedroom house with AC in charming Gloucester.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Gloucester at this delightful house. With three cozy bedrooms featuring a queen bed, a full bed, and a bunk be ...
From $748 per night (USD)VRBO
From $262 per night (USD)VRBO
Harbor View Apartment located in the heart of downtown Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Harbor View 2-bedroom, 1-bath apartment in downtown Gloucester with deck views of the Inner Harbor and the grounds ...
From $262 per night (USD)VRBO
From $914 per night (USD)VRBO
Stay at Windward Point
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. ✓ Direct waterfront setting with ...
From $914 per night (USD)VRBO
From $367 per night (USD)VRBO
House on tidal river, spacious deck, private yard
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the Captain’s Getaway where you can watch the tide ebb and flow all day long. Relax on the spacious deck of t ...
From $367 per night (USD)VRBO
From $564 per night (USD)VRBO
Close to Good Harbor Beach, 3 bedroom apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Located in a quiet neighborhood within a half mile of Good Harbor Beach, relax and enjoy the beauty of Gloucester. The ...
From $564 per night (USD)VRBO
From $1787 per night (USD)VRBO
Stay at Good Harbor Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Summary: Welcome to Stay Cape Ann, where exceptional homes meet local hospitality. This property features: ✓ 2-min ...
From $1787 per night (USD)VRBO
From $618 per night (USD)VRBO
Downtown Dahlias fully remodeled in the heart of Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relaxing spot close to everything in Gloucester. Our three bedroom home is a two level home filled with everything to ma ...
From $618 per night (USD)VRBO
From $399 per night (USD)VRBO
Walk to Good Harbor Beach. 3BR home, NEW Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
This lovely, tastefully decorated 3 BR home is 4/10 mile from the soft sands of spectacular Good Harbor Beach. Whether t ...
From $399 per night (USD)VRBO
From $223 per night (USD)VRBO
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please enjoy our fully renovated one bedroom, one bathroom cottage. It is a 5 minute walk to Long Beach, less a than 1 ...
From $223 per night (USD)VRBO
From $317 per night (USD)Expedia
Single Level Home - Steps to Downtown Gloucester & A/C throughout
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This darling property is private and steps to everything in Gloucester. We own both upstairs and downstairs units. The ...
From $317 per night (USD)Expedia
From $1062 per night (USD)VRBO
Changes in Latitude: Charming Niles Beach retreat next to Rocky Neck
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Changes in Latitude is a perfectly located vacation rental home for your Gloucester beach getaway. The house is an updat ...
From $1062 per night (USD)VRBO
From $1158 per night (USD)Expedia
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
This is the vacation house you have been looking for! Perfectly located only a few steps from the world famous Wingaersh ...
From $1158 per night (USD)Expedia
From $645 per night (USD)VRBO
Historic cottage is steps from the beach on a glorious seaside estate!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The "Studio" is a rustic stone cottage, originally built in 1905 as an artist's studio and expanded in the 1950s with a ...
From $645 per night (USD)VRBO
From $914 per night (USD)VRBO
Perfect Good Harbor Beach vacation home for large and/or extended family getaway
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 16
1st FL common kitchen, living room, dining room, full bath and sun room with pull out couch. First FL in-law apartment ...
From $914 per night (USD)VRBO
From $163 per night (USD)VRBO
WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Water Views from EVERY window, DECK & TV room overlooking Annisquam River. Harbor Views from Bedroom & Living room, ope ...
From $163 per night (USD)VRBO
Click For PricingExpedia
Long Beach House: Large, comfortable home just 285 ft from the white sands!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This large and comfortable vacation home is just steps from the white sands of Long Beach--a perfect summer location! Bu ...
Click For PricingExpedia
From $502 per night (USD)VRBO
Beautifully renovated OCEAN-FRONT luxury home on private beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
This is the house you've been looking for. Come and stay at this stunning custom-designed home on private Coffins Beach ...
From $502 per night (USD)VRBO
From $1691 per night (USD)Expedia
Annisquam Singing Pines: Riverfront Splendor
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Experience a Classic Cape Ann Summer at Annisquam Singing Pines Imagine spending your days swimming from the private do ...
From $1691 per night (USD)Expedia
From $808 per night (USD)VRBO
Salt Island Views: 4-Season Beach House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean- ...
From $808 per night (USD)VRBO
From $1263 per night (USD)Expedia
Over By Good Harbor: Phenomenal views!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home b ...
From $1263 per night (USD)Expedia
From $537 per night (USD)VRBO
~Walk to Good Harbor Beach: Adorable 4 bedroom/2 bath Dog Friendly~AC-Summer fun
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Very sunny, clean 4 bedrooms, 2 bath ranch home in a QUIET residential neighborhood, not far from Good Harbor beach and ...
From $537 per night (USD)VRBO
From $319 per night (USD)Expedia
Luxury Accommodations in Quiet Seaside Village
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Loft at Lane's Cove is a top floor, front to back unit with separate Queen bedroom and bath. Exposed high wood ceil ...
From $319 per night (USD)Expedia
From $684 per night (USD)VRBO
Garden by the Sea: Tranquil garden retreat at Good Harbor Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax and take in wonderful views of Gloucester's beautiful Good Harbor Beach, with Thatcher Island beyond, from this ch ...
From $684 per night (USD)VRBO
From $1233 per night (USD)VRBO
Coastal Oasis, Unobstructed, Direct Ocean Views. Ideal for all seasons!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Rare opportunity to book 30day+ offseason rental from 11/26 to 5/27. Work from home while you listen and watch the waves ...
From $1233 per night (USD)VRBO
From $451 per night (USD)VRBO
Rarely Available Ocean Facing Walkable to Good Harbor Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy beautiful, unobstructed ocean views from this well appointed 1BR unit at less than hotel prices! Short stroll to f ...
From $451 per night (USD)VRBO
From $270 per night (USD)VRBO
Cozy, Waterview Old Quarryman boarding house
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Adorable 1 bedroom (with memory foam folding cot for xtra guests) Sleep Sofa. Has foma topper, High ceilings, laundry, ...
From $270 per night (USD)VRBO
From $703 per night (USD)VRBO
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your very own summer beach home! Located a short 3 minute walk from good harbor beach, this two level single ...
From $703 per night (USD)VRBO
From $1260 per night (USD)Expedia
Two Beaches: Long Beach & Good Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Ideally situated between two of Cape Ann's most beautiful beaches, this ideal vacation rental home is a mere 3-minute wa ...
From $1260 per night (USD)Expedia
From $670 per night (USD)VRBO
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Riverdock Cottage was completely renovated in 2017 and has received some new updates for the 2022 rental season, includi ...
From $670 per night (USD)VRBO
From $1043 per night (USD)VRBO
The Aerie. 2 King beds, AC, outdoor shower. Walk to 2 local beaches
- Bedrooms:
- 1
- Bathrooms:
- 8
- Sleeps:
- 16
Welcome to Aerie! Enjoy this grand gathering house with great flow and enough rooms for all the beach lovers in your lif ...
From $1043 per night (USD)VRBO
From $1247 per night (USD)VRBO
NEW Rental: 2 min walk to Private Coffin's Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy this fantastic beach house just a quick 5 minute walk to Coffin's Beach. → Sleeps 10 → 1 King bed, 2 Twin beds, ...
From $1247 per night (USD)VRBO
From $335 per night (USD)VRBO
Walk to Good Harbor Beach, pet friendly, family beach home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a memorable family vacation in this fully furnished, 3 bedroom single-family home with deck, yard and marsh views, ...
From $335 per night (USD)VRBO
From $982 per night (USD)VRBO
Squam Light: Nestled in the heart of Annisquam
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the ...
From $982 per night (USD)VRBO
From $674 per night (USD)VRBO
The Haabah Beach Retreat—4 Minute Walk to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Two-bedroom gorgeous beach house overlooking Good Harbor Beach, located DIRECTLY on the Good Harbor estuary. The house i ...
From $674 per night (USD)VRBO
From $286 per night (USD)VRBO
VIEWS! Annisquam Bridge House at Lobster Cove. Cancellation 9/30 - 10/9
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Annisquam Bridge House-a renovated second floor unit high above Lobster Cove, Perfect getaway for a couple. It can acco ...
From $286 per night (USD)VRBO
From $981 per night (USD)Expedia
Sunset Cove: Waterfront living on the Annisquam River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river an ...
From $981 per night (USD)Expedia
From $983 per night (USD)VRBO
Thurston Point: Deepwater River Dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurst ...
From $983 per night (USD)VRBO
From $836 per night (USD)Expedia
Helena House: Charming and serene, close to Plum Cove Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers peekaboo views of Ipswich Bay from the se ...
From $836 per night (USD)Expedia