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From $187 per night (USD)
VRBO
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 ...
From $187 per night (USD)
VRBO
From $236 per night (USD)
Expedia
A tranquil ocean retreat steps from the water's edge
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
On the Cove is a spacious three-room apartment is located directly on Lanes Cove in Lanesville (Gloucester) with spectac ...
From $236 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Beach cottage walkable to Good Harbor and Long Beach- RENOVATED!
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 $346 per night (USD)
VRBO
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Expedia
Stanwood Point: Waterfront cottage with dock, large screened porch, and yard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large 3 bedroom waterfront cottage on the Little river with a tidal dock. Large fireplaced living room, huge screened po ...
Click For Pricing
Expedia
From $1025 per night (USD)
VRBO
Elegant Gloucester Beach Getaway with Ocean Views!
Bedrooms:
2
Bathrooms:
6
Sleeps:
11
Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for ...
From $1025 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Long Beach Gloucester 2 minute walk to Beach. Large PVT yard & gardens. Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FROM SEPTEMBER 14 - SEPTEMBER 23 WE ARE OFFERING A 10% DISCOUNT FOR A 7 NIGHT BOOKING. WE ARE ALSO OFFERING YOU THE OP ...
From $527 per night (USD)
Expedia
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VRBO
Seaside Escape just steps to Good Harbor beach in Gloucester
Bedrooms:
2
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 ...
Click For Pricing
VRBO
From $306 per night (USD)
Expedia
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!
Bedrooms:
3
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 $306 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Apartment in historic home across from Cripple Cove Harbour, Gloucester, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Are you ready to sit back, relax and enjoy all that Gloucester has to offer? Then this desirable East Gloucester apartm ...
From $225 per night (USD)
VRBO
From $431 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 $431 per night (USD)
VRBO
$Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away$
From $614 per night (USD)
VRBO
Gorgeous New Home w\/ Ocean Views- 2 Private Beaches Steps Away
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
THE HOME: This house was built in 2018 with every modern amenity and comfort for vacation life. Vaulted ceilings in the ...
From $614 per night (USD)
VRBO
Click For Pricing
Expedia
COME STAY AT THE MERMAID COTTAGE ON LANES COVE !
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The mermaid cottage is a sunny quaint cottage with a large sunny kitchen, cozy living room, and large upstairs bedroom w ...
Click For Pricing
Expedia
$Romantic Summerwind Cottage, Scenic Harbor View w\/Deck!$
From $371 per night (USD)
VRBO
Romantic Summerwind Cottage, Scenic Harbor View w\/Deck!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to the ROMANTIC SUMMERWIND COTTAGE and enjoy the scenic view of Gloucester harbor. Relax, unwind, and dine in sty ...
From $371 per night (USD)
VRBO
From $177 per night (USD)
Expedia
La Bohème RETREAT - UNPLUG, UNWIND & UPLIFT your spirits!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
NO WIFI or TV. For those seeking to truly rest, relax, rejuvenate and contemplate their journey on earth. Our retreat ...
From $177 per night (USD)
Expedia
Click For Pricing
VRBO
A walk up to heaven!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Very cozy Victorian home Fully renovated with brand new furniture and fresh paint Very convenient and plus location 5 ...
Click For Pricing
VRBO
From $318 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 $318 per night (USD)
Expedia
From $619 per night (USD)
VRBO
Beautiful 3 bed home...steps from Good Harbor and Long Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Renovate beach home, steps from two of New England's most beautiful beaches, Good Harbor and Long Beach! This beautiful ...
From $619 per night (USD)
VRBO
Click For Pricing
Expedia
Quaint Home, Near Good Harbor Beach and Town, Great for Families
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
This is a classic Gloucester home, nothing fancy, more like a home away from home for your family. In fact, my family of ...
Click For Pricing
Expedia
From $868 per night (USD)
VRBO
GOT BEACH! Good Harbor House
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Location, Location, Location! Get ready to do some serious relaxing at this beautiful and comfortable, 4 bedroom house ...
From $868 per night (USD)
VRBO
From $510 per night (USD)
Expedia
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Bedrooms:
3
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 $510 per night (USD)
Expedia
Click For Pricing
VRBO
Turning Tide Cottage on the Rivier
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Nice deck with water views, small swimming beach,Bar-B-Que, large back lawn, on Annasquam river, close to downtown, easy ...
Click For Pricing
VRBO
From $129 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 $129 per night (USD)
Expedia
$Charming cottage near the ocean w\/beach access & near Gloucester$
From $198 per night (USD)
VRBO
Charming cottage near the ocean w\/beach access & near Gloucester
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Good Harbor Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $198 per night (USD)
VRBO
From $574 per night (USD)
Expedia
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 $574 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Walk to Good Harbor and Long Beach -Vacation Home
Bedrooms:
3
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 7). ...
From $401 per night (USD)
VRBO
From $380 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 $380 per night (USD)
VRBO
$Quaint Neighborhood \/ Close to Beaches$
From $179 per night (USD)
VRBO
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 $179 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Annisquam Village Bunny Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
This beautiful Annisquam Village cottage was renovated to the highest level of quality by two artist's. Located just 5 ...
From $251 per night (USD)
Expedia
$Amazing Waterfront\/Access 4BDRM in Riggs Point$
From $500 per night (USD)
VRBO
Amazing Waterfront\/Access 4BDRM in Riggs Point
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Come and relax at our amazing home fully equipped with everything to make you feel right at home. With spacious rooms to ...
From $500 per night (USD)
VRBO
$Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!\n$
From $388 per night (USD)
Expedia
Beach Gem overlooking Stage Fort Park, Tablet Rock & Cressy's Beach!!!\n
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 $388 per night (USD)
Expedia
From $1973 per night (USD)
VRBO
Private Section of Wingaersheek Beach Front Home on top of the dunes.
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
Our home since 1979 where our children grew up now offers other families to enjoy this very special location and home. ...
From $1973 per night (USD)
VRBO
$Massachusetts Abode w\/ Deck & Grill: Near Beaches!$
From $244 per night (USD)
Expedia
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 $244 per night (USD)
Expedia
$Centrally located open concept apartment with parking, central AC, & W\/D$
From $275 per night (USD)
VRBO
Centrally located open concept apartment with parking, central AC, & W\/D
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Paula's Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $275 per night (USD)
VRBO
From $398 per night (USD)
Expedia
Beachmont: 3 bedroom house near beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Just 1/3 of a mile from Good Harbor Beach in East Gloucester! Enjoy a relaxing beach getaway in Historic Gloucester, MA. ...
From $398 per night (USD)
Expedia
$Peaceful centrally located home: w\/ yard & walking distance to town$
From $541 per night (USD)
VRBO
Peaceful centrally located home: w\/ yard & walking distance to town
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Gloucester Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $541 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
$Stroll to SeaView\/Beach; Great Yard$
From $579 per night (USD)
VRBO
Stroll to SeaView\/Beach; Great Yard
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
The Ledge House is an idyllic retreat nestled in the heart of Gloucester's charming Bay View village. The historic farmh ...
From $579 per night (USD)
VRBO
From $1106 per night (USD)
Expedia
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 $1106 per night (USD)
Expedia
From $535 per night (USD)
VRBO
One of a kind ocean front property - private section of Wingaersheek Beach.
Bedrooms:
3
Bathrooms:
1
Sleeps:
4
This property offers stunning views from every vantage point of Coffin's Beach, Crane Beach, the New Hampshire and Main ...
From $535 per night (USD)
VRBO
From $1037 per night (USD)
VRBO
Zzz Good Harbor Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Summary: ✔ Just a 2-minute walk to the renowned Good Harbor Beach ✔ Expansive home featuring 1 King, 2 Queens, 2 Fulls, ...
From $1037 per night (USD)
VRBO
From $370 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 $370 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Prime Gloucester Property Overlooking Inner Harbor - CLOSING DECEMBER 15, 2024
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We are closing our vacation rental at the end of 2024 for personal reasons. This 2BR/2BA apartment comfortably ac ...
From $195 per night (USD)
Expedia
$Newly Renovated One Bedroom Cottage - Walk to Long Beach\/Good Harbor Beach$
From $180 per night (USD)
VRBO
Newly Renovated One Bedroom Cottage - Walk to Long Beach\/Good Harbor Beach
Bedrooms:
1
Bathrooms:
2
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 $180 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Walk to Good Harbor Beach. 3BR home, NEW Kitchen
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This lovely, tastefully decorated 3 BR home is 4/10 mile from the soft sands of spectacular Good Harbor Beach. Whether t ...
From $274 per night (USD)
VRBO
$Single Level Home - Steps to Downtown Gloucester & A\/C throughout$
From $350 per night (USD)
VRBO
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 $350 per night (USD)
VRBO
From $1005 per night (USD)
Expedia
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Location, location, location! This vacation home is large and comfortable and is just steps to the white sands and surf ...
From $1005 per night (USD)
Expedia
From $945 per night (USD)
VRBO
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 $945 per night (USD)
VRBO
Click For Pricing
Expedia
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the views, breezes and scent of the sea from this lofty perch overlooking Gloucester's famed waterfront. Stacy Bou ...
Click For Pricing
Expedia
$Perfect Good Harbor Beach vacation home for large and\/or extended family getaway$
From $681 per night (USD)
VRBO
Perfect Good Harbor Beach vacation home for large and\/or extended family getaway
Bedrooms:
6
Bathrooms:
6
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 $681 per night (USD)
VRBO
From $1044 per night (USD)
Expedia
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Waterfront on Gloucester’s Rocky Neck. Swim from your private beach or from your tidal dock and enjoy the waters of scen ...
From $1044 per night (USD)
Expedia
From $1164 per night (USD)
VRBO
Long Beach House: Large, comfortable home just 285 ft from the white sands!
Bedrooms:
3
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 ...
From $1164 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Newly 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 a private beach on the ...
From $454 per night (USD)
VRBO
From $689 per night (USD)
VRBO
Over By Good Harbor: Phenomenal views and just 0.2 miles to the beach.
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Just up the street from Good Harbor Beach, this well-appointed and perfectly located vacation rental is the ideal home b ...
From $689 per night (USD)
VRBO
From $1649 per night (USD)
Expedia
Golden Sands at Good Harbor: Just walk across the street to the beach.
Bedrooms:
4
Bathrooms:
7
Sleeps:
12
Golden Sands is the quintessential turn of the century Gloucester beach "cottage." With views of Good Harbor Beach, the ...
From $1649 per night (USD)
Expedia
From $364 per night (USD)
VRBO
Harbor View House, Walk to Beach, Sunsets from Deck
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Renovated comfortable house with big backyard deck overlooking Gloucester harbor and gorgeous sunsets. Expansive perenni ...
From $364 per night (USD)
VRBO
From $1115 per night (USD)
Expedia
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at An ...
From $1115 per night (USD)
Expedia
From $678 per night (USD)
VRBO
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Good Harbor Beach, one of Gloucester's finest stretches of sand, is just a five minute walk from this comfortable ocean- ...
From $678 per night (USD)
VRBO
From $397 per night (USD)
VRBO
WATERFRONT- River & Harbors views, Walking Distance to Downtown, Beaches & Park
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Water Views from EVERY window, DECK & TV room overlooking Annisquam River. Harbor Views from Bedroom & Living room, ope ...
From $397 per night (USD)
VRBO
From $518 per night (USD)
VRBO
Terra Nova Cottage Waterfront! Enjoy stunning views & sunsets over the Annisquam
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Greet each day with inspiring views of the Annisquam River from this charming vacation home and enjoy the most spectacul ...
From $518 per night (USD)
VRBO
From $289 per night (USD)
VRBO
Rarely Available Ocean Facing Walkable to Good Harbor Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy beautiful, unobstructed ocean views from this well appointed 1BR unit at less than hotel prices! Short stroll to f ...
From $289 per night (USD)
VRBO
From $179 per night (USD)
VRBO
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 $179 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the 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 br ...
From $364 per night (USD)
Expedia
From $1080 per night (USD)
VRBO
Sea Fox: Custom-designed home with rights to private Coffins Beach.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This bright and open contemporary vacation rental home was custom-designed and built by the architect owner. The care an ...
From $1080 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Coastal Oasis with Unobstructed, Direct Ocean Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Incredible wrap around, direct ocean views and walkable to Good Harbor Beach! Beautifully appointed and maintained unit. ...
From $590 per night (USD)
VRBO
$~Walk to Good Harbor Beach: Adorable 4 bedroom\/2 bath Dog Friendly~AC-Summer fun$
From $468 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 and recently updated - 4 bedrooms, 2 bath home, (one bed is in separate in-law with bathroom) ranch, w ...
From $468 per night (USD)
VRBO
From $298 per night (USD)
VRBO
Breeze of Gloucester
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
2 Bedrooms, 1 Full Bath, Sleeps 6 Come to discover the hidden treasure of east coast – Cape Ann. Our home is in a lovel ...
From $298 per night (USD)
VRBO
From $208 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 $208 per night (USD)
VRBO
From $512 per night (USD)
VRBO
Waterfront Living w Stunning Views, Beautiful Decor, Kayaks, Private drive
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Riverdock Cottage was completely renovated in 2017 and has received some new updates for the 2022 rental season, includi ...
From $512 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Annisquam River Sunsets: Enjoy spectacular sunsets and a relaxed river vibe.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You'll find river life at its best when you stay at this newly-built vacation rental home that sits along the banks of s ...
From $586 per night (USD)
VRBO
Click For Pricing
Expedia
Jewel Box: A gem of a rental home close to Good Harbor Beach.
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Situated at the end of a quiet street and down the road from Good Harbor Beach, Jewel Box is a gem of a rental home. Thi ...
Click For Pricing
Expedia
From $698 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 $698 per night (USD)
VRBO
From $1039 per night (USD)
Expedia
Two Beaches: Walk to Long Beach or Good Harbor!
Bedrooms:
2
Bathrooms:
4
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 $1039 per night (USD)
Expedia
Click For Pricing
VRBO
Ships Bell: Water views and amazing sunsets on a quiet street in Lanesville.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Picture yourself on the huge wraparound deck of Ships Bell House, enjoying the setting of the sun over breathtaking wate ...
Click For Pricing
VRBO
From $651 per night (USD)
Expedia
Plaisance: Enjoy the best of Gloucester living.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Plaisance is a comfortable modern home nestled in a quiet, leafy neighborhood not far from Good Harbor Beach. The ground ...
From $651 per night (USD)
Expedia
From $657 per night (USD)
VRBO
Sunset Cove: Waterfront home in Goose Cove section of Gloucester.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Waterfront on the Annisquam River in Gloucester, this exceptional vacation rental boasts wonderful views of the river an ...
From $657 per night (USD)
VRBO
From $824 per night (USD)
Expedia
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Bedrooms:
2
Bathrooms:
5
Sleeps:
7
Get away from it all and unwind at this comfortable riverfront vacation retreat. Located in a quiet neighborhood, Thurst ...
From $824 per night (USD)
Expedia
From $791 per night (USD)
VRBO
Helena House: European flair, close to Plum Cove Beach.
Bedrooms:
3
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 $791 per night (USD)
VRBO
From $985 per night (USD)
Expedia
Squam Light: A newly renovated cottage, nestled in the village of Annisquam.
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the ...
From $985 per night (USD)
Expedia
From $609 per night (USD)
VRBO
The Haabah Beach Retreat—4 Minute Walk to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Two-bedroom gorgeous beach house overlooking Good Harbor Beach, located DIRECTLY on the Good Harbor estuary. The house i ...
From $609 per night (USD)
VRBO
From $220 per night (USD)
VRBO
VIEWS! Annisquam Bridge House at Lobster Cove. June dates discounted.
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 $220 per night (USD)
VRBO
From $511 per night (USD)
VRBO
Wingaerchic: A hidden retreat near Gloucester's sandy Wingaersheek Beach.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This very private contemporary house is perched on a shady hilltop near Gloucester's sandy Wingaersheek Beach. It's spac ...
From $511 per night (USD)
VRBO
From $869 per night (USD)
VRBO
The Aerie. 2 King beds, AC, outdoor shower. Walk to 2 local beaches
Bedrooms:
2
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 $869 per night (USD)
VRBO
From $669 per night (USD)
VRBO
Changes in Latitude: Charming cottage close to Niles Beach and 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 $669 per night (USD)
VRBO
From $1090 per night (USD)
VRBO
NEW Rental: 2 min walk to Private Coffin's Beach
Bedrooms:
2
Bathrooms:
3
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 $1090 per night (USD)
VRBO
From $463 per night (USD)
VRBO
Walk to Good Harbor Beach, pet friendly, family beach home
Bedrooms:
2
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 $463 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Joseph's Way: A charming cottage in a quiet setting, near Good Harbor Beach.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Just 4/10 of a mile from Gloucester's sandy Good Harbor Beach, Joseph's Way is delightful two bedroom property is nestle ...
From $610 per night (USD)
Expedia
From $821 per night (USD)
VRBO
Good Harbor Beachfront at the Footbridge
Bedrooms:
2
Bathrooms:
6
Sleeps:
10
Single family house, over one hundred years old, accommodates ten. Three queen beds, one double bed with a trundle, and ...
From $821 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Spacious Modern Beach House- Steps to Long Beach and Good Harbor
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Just steps to Long Beach, or a 10 minute walk to Good Harbor Beach, enjoy this clean, modern new single family home with ...
From $717 per night (USD)
VRBO
From $207 per night (USD)
VRBO
Ocean and Woods! Best of both seaside delights in Gloucester!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you are a nature lover, you'll love our location. 200 yards or so in either direction will lead you to treasured hab ...
From $207 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Gloucester: 5 Bedroom Summer Cottage with Sunset Views and Private Beach Access
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
This finely maintained summer cottage built in the 1820s overlooks Hodgkins Cove in Gloucester Massachusetts. Unique an ...
From $586 per night (USD)
VRBO
From $977 per night (USD)
VRBO
Beautiful Oceanfront Home in Estate Setting, Gloucester
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
A spacious, beautiful contemporary home on a private oceanfront estate near Gloucester's coveted Annisquam district, wit ...
From $977 per night (USD)
VRBO
$WaterViews Overlooking Gloucester Inner Harbor \/Sunroom\/ Deck \/Walk to Town\/ AC$
From $469 per night (USD)
VRBO
WaterViews Overlooking Gloucester Inner Harbor \/Sunroom\/ Deck \/Walk to Town\/ AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
VACATION or WORK or do a bit of both if it means you'll have longer to play here on Cape Ann! The preferred spot for all ...
From $469 per night (USD)
VRBO
From $578 per night (USD)
VRBO
Summer Cottage on Ipswich Bay
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This quiet summer cottage was built in the 1890's, it's original charm has been retained, while updates have made it a c ...
From $578 per night (USD)
VRBO
$\Rocky Neck Hideaway\ on Wonson Cove, Rocky Neck - Gloucester$
From $252 per night (USD)
Expedia
\"Rocky Neck Hideaway\" on Wonson Cove, Rocky Neck - Gloucester
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
<b>Enjoy the ambiance of a New England Seaside Getaway, without the crowds!</b> <i>Quick Note: We have a two night mini ...
From $252 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Peaceful retreat, newly-renovated, short walk to Good Harbor Beach + WIFI
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy your vacation sojourn in this newly-renovated home, a short walk to one of New England's most beautiful beaches. ...
From $352 per night (USD)
VRBO
From $361 per night (USD)
VRBO
Bayview Guest Cottage
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
This property is a 650 sq. foot cozy cottage on Ipswich Bay with unbeatable views facing west, making for beautiful suns ...
From $361 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Private, Single Family Beach House, Right at Good Harbor Beach foot bridge
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
*Please; CONTACT HOST FOR MULTI-MONTH and OFF SEASON RATES* Real beach house on one of Boston areas most beautiful an ...
From $235 per night (USD)
VRBO
From $139 per night (USD)
VRBO
Gloucester Studio - Om Suite Om~ near Good Harbor Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Om Suite Om is a comfortable, cozy and convenient studio efficiency space, with a separate key and entry, in the lower l ...
From $139 per night (USD)
VRBO
From $380 per night (USD)
VRBO
Seaside Village of Lanesville - North Gloucester, MA
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This quaint, cozy, quiet two bedroom fully furnished apartment in the Village of Lanesville has views of the Ipswich Bay ...
From $380 per night (USD)
VRBO
From $358 per night (USD)
VRBO
Sunset Views, Waterfront Property, Dock - Sleeps 12
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Stunning sunsets, a parade of boats going by, a charming marina, and a beach brimming with natural beauty — these are th ...
From $358 per night (USD)
VRBO

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