Squam Rock Pasture Rentals
- From $2709 per night (USD)
VRBO
Elegant Bayview Victorian Home - Walk to Beach
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
A unique private estate, rich in history and natural beauty. The home was the residence of Benjamin F. Butler, the color ...
From $2709 per night (USD)VRBO
- From $447 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 $447 per night (USD)VRBO
- From $350 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 $350 per night (USD)VRBO
- From $1061 per night (USD)
VRBO
⭐️ Beautiful 4+ Bedroom Annisquam W\/ Private Beach Access 🏖
- Bedrooms:
- 0
- Bathrooms:
- 5
- Sleeps:
- 12
This a beautifully constructed, family-friendly 4 bedroom, 4 full bathroom home in the heart of Annisquam, one of the mo ...
From $1061 per night (USD)VRBO
- From $629 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 $629 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $698 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 $698 per night (USD)VRBO
- From $977 per night (USD)
Expedia
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)Expedia
- From $540 per night (USD)
VRBO
Vacation home. Walk to Diamond Cove & Annisquam Land Trust Lighthouse Beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Relax at the scenic New England coastline at Diamond Cove. Access 2 member beaches within walking distance. Experience ...
From $540 per night (USD)VRBO
- From $363 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 $363 per night (USD)VRBO
- From $495 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 $495 per night (USD)VRBO
- From $1098 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 $1098 per night (USD)VRBO
- From $458 per night (USD)
VRBO
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 $458 per night (USD)VRBO
- From $242 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 $242 per night (USD)VRBO
- From $558 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 $558 per night (USD)VRBO
- From $704 per night (USD)
Expedia
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 $704 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- 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 $572 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 $572 per night (USD)VRBO
- From $540 per night (USD)
Expedia
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 $540 per night (USD)Expedia
- 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 $1083 per night (USD)
Expedia
Beachfront retreat at your private beach Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Escape to the stunning private beach house 3-bedroom vacation home in Gloucester, where the ocean breeze and the sound o ...
From $1083 per night (USD)Expedia
- From $363 per night (USD)
VRBO
Charming cottage on seaside estate offers gorgeous views, private beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
"Little Driftwood" is a sweet and cozy, very small cottage with a rustic minimalist style, a gorgeous water view, and fu ...
From $363 per night (USD)VRBO
- From $959 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 $959 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Airy, book-lined cottage on historic seaside estate with private beaches & more
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a heavenly stay on this historic private estate, with full access to two private beaches, a granite swimming pier, ...
From $299 per night (USD)VRBO
- From $622 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 $622 per night (USD)Expedia
- From $543 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 $543 per night (USD)VRBO
- From $279 per night (USD)
VRBO
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 $279 per night (USD)VRBO
- From $245 per night (USD)
VRBO
NEW 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 $245 per night (USD)VRBO
- From $846 per night (USD)
VRBO
Victorian house on private estate with beaches, tennis and views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Old family house, Victorian style with mansard roof has all modern conveniences. Kitchen is fully equipped. Living room ...
From $846 per night (USD)VRBO
- 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 $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
- Click For Pricing
VRBO
Riverfront luxury in Gloucester.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this stunning 4 bedroom, 3 bathroom vacation rental overlooking the picturesque Mill River, with views out to ...
Click For PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- 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
- From $563 per night (USD)
Expedia
Waterfront Bliss in Gloucester: 3BR, Dock & Patio, Sleep 10
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Waterfront Escape - The Views Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $563 per night (USD)Expedia
- From $522 per night (USD)
VRBO
Zzz Lighthouse Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Summary: Visit @ZzzLighthouseBeach on IG to discover our stunning home and local recommendations! ✔ Short 8 min stroll ...
From $522 per night (USD)VRBO
- From $258 per night (USD)
Expedia
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 $258 per night (USD)Expedia
- From $2234 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 $2234 per night (USD)VRBO
- From $3351 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 $3351 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