Squam Rock Pasture Rentals
From $705 per night (USD)VRBO
Squam Light: Nestled in the heart 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 $705 per night (USD)VRBO
From $475 per night (USD)Expedia
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 $475 per night (USD)Expedia
From $1065 per night (USD)VRBO
Elegant Gloucester Beach Getaway with Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 10
Nestled in a private section of Wingaersheek Beach, this bright Gloucester vacation rental home is a tranquil escape for ...
From $1065 per night (USD)VRBO
From $878 per night (USD)Expedia
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 $878 per night (USD)Expedia
From $638 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 $638 per night (USD)VRBO
From $549 per night (USD)Expedia
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 $549 per night (USD)Expedia
From $251 per night (USD)VRBO
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)VRBO
From $477 per night (USD)Expedia
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 $477 per night (USD)Expedia
From $834 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 $834 per night (USD)VRBO
From $655 per night (USD)Expedia
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 $655 per night (USD)Expedia
From $681 per night (USD)VRBO
Elegant Bayview Victorian Home; walk to beach
- Bedrooms:
- 3
- 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 $681 per night (USD)VRBO
From $1384 per night (USD)Expedia
Wingaersheek, Private and Public Beach Luxury Home
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
This home is perfectly located a few steps from the beach with an a rooftop with outstanding water views. The house is ...
From $1384 per night (USD)Expedia
From $943 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 $943 per night (USD)VRBO
From $995 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 $995 per night (USD)Expedia
From $736 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 $736 per night (USD)VRBO
From $591 per night (USD)Expedia
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 $591 per night (USD)Expedia
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 $694 per night (USD)Expedia
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 $694 per night (USD)Expedia
From $566 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 $566 per night (USD)VRBO
From $1895 per night (USD)Expedia
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 $1895 per night (USD)Expedia
From $727 per night (USD)VRBO
Evensong: Oceanview Retreat with Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Unobstructed Water Views of The Annisquam in this newly-renovated "walls of glass" home boasting panoramic views of The ...
From $727 per night (USD)VRBO
From $450 per night (USD)Expedia
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 $450 per night (USD)Expedia
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 $632 per night (USD)Expedia
Wingaerchic: Woodsy retreat in West Gloucester
- 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 $632 per night (USD)Expedia
From $1119 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 $1119 per night (USD)VRBO
From $290 per night (USD)Expedia
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 $290 per night (USD)Expedia
From $1648 per night (USD)VRBO
Stay at Lighthouse Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: ✔ Short 8 min stroll to Lighthouse Beach ✔ Private, peaceful wooded setting in magical Annisquam ✔ 5 comfy beds ...
From $1648 per night (USD)VRBO
From $1105 per night (USD)Expedia
Oceanfront Dock Escape ~ Kayaks & Paddleboards
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: This 4-bedroom house is in a prime location & has EVERYTHING you need for an amazing vacation to Gloucester, M ...
From $1105 per night (USD)Expedia
From $908 per night (USD)VRBO
Maids Quarters; private beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This simple and quiet home is behind a Victorian mansion and was used as the Maid's quarters to house staff. It's now a ...
From $908 per night (USD)VRBO
From $1264 per night (USD)Expedia
Elegant Victorian & Quarters
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 16
A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the color ...
From $1264 per night (USD)Expedia
From $1145 per night (USD)VRBO
Privacy and a water view, five minutes to a private beach.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Annisquam has a quaint village and from this house, there are lovely walks, taking in beaches and classic New England ho ...
From $1145 per night (USD)VRBO
From $412 per night (USD)Expedia
Antique Cottage RARE PRIVATE SAUNA Lighthouse Beach Nearby Trails Firepit
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
- This cozy antique cottage with historic charm is in a quiet tucked away neighborhood of Gloucester - the perfect spot ...
From $412 per night (USD)Expedia
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Panoramic Ocean View; walk to private beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Escape with the entire family to this serene retreat, where tranquility meets breathtaking beauty: Perched above Ipswic ...
Click For PricingVRBO
From $1121 per night (USD)Expedia
Private Beach! Dream vacation at your private beach in Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to this stunning private beach and enjoy this beach house with 3 bedroom. The ocean breeze and the sound of crash ...
From $1121 per night (USD)Expedia
From $1141 per night (USD)VRBO
Waterfront Wingaersheek Beach Unobstructed Panoramic Ocean and Lighthouse Views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At the end of a road, perched on rocks, this remarkably sited year-round waterfront home accesses sparkling smooth white ...
From $1141 per night (USD)VRBO
From $461 per night (USD)Expedia
Cape Ann Reset
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clear your head and relax in the Bayview neighborhood of Gloucester. Our comfortable home offers separate sitting areas ...
From $461 per night (USD)Expedia