Gloucester Rentals
From $555 per night (USD)VRBO
Magnolia Ocean View Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Comfy cottage with stunning ocean views in the heart of Magnolia village. Convenient to beaches, stores and restaurant ...
From $555 per night (USD)VRBO
From $663 per night (USD)Expedia
Luxury Home in the Heart of Rockport
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Gorgeous house in Rockport, steps to beach, town, train, Shalin Liu performance center! This home is located on a quiet ...
From $663 per night (USD)Expedia
From $496 per night (USD)VRBO
Ocean View - Great Location | Beautiful, Warm & Spacious.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Sun-filled vacation house with water view in the beautiful Magnolia town in Gloucester. MA (CAPE ANN). This charming, b ...
From $496 per night (USD)VRBO
From $1149 per night (USD)Expedia
Long Beach & Private Good Harbor Beach, Beautiful Luxury Home, Ext'd Famil
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
This is the Vacation Beach House you have been searching for. Perfectly located only steps to Long Beach Gloucester, thi ...
From $1149 per night (USD)Expedia
From $659 per night (USD)VRBO
Waterfront Home with Spectacular Viewsof the Annisquam River
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Watch the beautiful sunsets over the Annisquam River from the deck or just enjoy the scenic views all day long of Mercha ...
From $659 per night (USD)VRBO
From $400 per night (USD)VRBO
3 Bedroom Two Bath Walk to Long Beach and Good Harbor Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
My husband and I want to assure you that we take your family's health and safety very seriously. Our house is professio ...
From $400 per night (USD)VRBO
From $959 per night (USD)VRBO
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
This is the vacation house you have been looking for! It’s perfectly located only a few steps from the private & seclude ...
From $959 per night (USD)VRBO
From $1373 per night (USD)VRBO
Secluded, 180 Degree View Of Wingaersheek Beach From High Up On The Dunes
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private, newly renovated beach house on hilltop overlooking two mile white sand Wingaersheek Beach with access and 5 car ...
From $1373 per night (USD)VRBO
From $542 per night (USD)VRBO
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This recently renovated beach themed 3 level, 3 bedroom, 2.5 baths, fully stocked condo, has 2 unique outdoor spaces, an ...
From $542 per night (USD)VRBO
From $695 per night (USD)Expedia
PREMIUM PROPERTY - Private 2-Acre Retreat - MODERN 4 Bedrooms - See Video Tour
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
*NEW: We recently completed a full upgrade and modernization of the kitchen. In addition, we just completed a massive l ...
From $695 per night (USD)Expedia
From $476 per night (USD)VRBO
Walk To Good Harbor, OCEAN VIEWS, Open All Year!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: You and your family cannot beat this amazing Gloucester location, walking distance to the best beach in all of ...
From $476 per night (USD)VRBO
From $187 per night (USD)Expedia
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)Expedia
From $369 per night (USD)VRBO
Ocean Views in this Charming 2 bedroom Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Charming two bedroom cottage. The property has a wonderful open kitchen and dining room that gives way to an ocean facin ...
From $369 per night (USD)VRBO
From $237 per night (USD)Expedia
River's Edge: A charming 2BR riverfront home in Gloucester.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Exquisitely renovated by the owner-architect, every detail of this charming vacation home has been thoughtfully consider ...
From $237 per night (USD)Expedia
From $949 per night (USD)VRBO
Ocean front and 3 beaches across,parks, short walk to historic downtown!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy the most amazing ocean views and the best location in Gloucester! The house is right on the Boulevard in Glouceste ...
From $949 per night (USD)VRBO
From $1137 per night (USD)Expedia
Bell View: Private tennis court and an in-law suite.
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Your Gloucester vacation experience awaits you in this spacious and versatile vacation home. Bell View can accommodate u ...
From $1137 per night (USD)Expedia
From $411 per night (USD)VRBO
4 Bedroom LUX House\/with Pool Next Door
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Nestled on private street in beautiful West Gloucester, this large vacation rental (you get the entire house-- not just ...
From $411 per night (USD)VRBO
From $550 per night (USD)VRBO
Experience seaside charm near Good Harbor Beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Come and enjoy this new home with roof top deck overlooking Good Harbor Beach. We are a 5 minute walk to the beach! We ...
From $550 per night (USD)VRBO
From $635 per night (USD)VRBO
Featured on HGTV's Beach Hunters
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Golden Cottage by the Sea, is a true New England Cottage that has been lovingly restored and updated. This quaint 1830's ...
From $635 per night (USD)VRBO
Click For PricingExpedia
Private, Light Filled & Convenient Wingaersheek Beach Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming, private, light filled home with newer addition in quiet neighborhood near Wingaersheek Beach. Large Master be ...
Click For PricingExpedia
From $624 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 $624 per night (USD)VRBO
From $447 per night (USD)Expedia
The Nest at Pigeon Cove: Modern farmhouse with all the comforts of home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Perfect for a winter holiday retreat! Nestled in the Pigeon Cove neighborhood, a sweet little spot between beaches/Bear ...
From $447 per night (USD)Expedia
From $292 per night (USD)VRBO
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 $292 per night (USD)VRBO
From $429 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 $429 per night (USD)VRBO
From $239 per night (USD)VRBO
Holbrook House: Charming Rockport Village House, Walk To Everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A cozy, lovingly restored 1950's house. Walking distance to all that Rockport village and Bear Skin Neck has to offer. ...
From $239 per night (USD)VRBO
From $199 per night (USD)VRBO
Good Harbor Beach Apt.- 6\/10 mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom apt.- sleeps up to 4 ( 2 adults, 2 children) Bedroom has a queen size bed. The living room has sleepi ...
From $199 per night (USD)VRBO
From $370 per night (USD)VRBO
Good Harbor Beach Retreat ~ Walk to beach, shops, restaurants ~Dog Friendly
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Our adorable, 3 bedroom home is in a prime location for your vacation, with plenty of windows for ocean breezes. If yo ...
From $370 per night (USD)VRBO
From $497 per night (USD)Expedia
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 $497 per night (USD)Expedia
From $405 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 $405 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
From $1313 per night (USD)VRBO
Elegant Italian Villa On The Scenic Coast of New England
- Bedrooms:
- 6
- Bathrooms:
- 10
- Sleeps:
- 18
Villa Fiori in scenic Manchester-by-the-sea is a short walk from local Black & White Beach and a 3 minute drive from the ...
From $1313 per night (USD)VRBO
From $238 per night (USD)VRBO
Lanesville Cove Retreat Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our serene, open floor plan home features everything you need for a short stay or a long term get away. Our goal was co ...
From $238 per night (USD)VRBO
From $727 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 $727 per night (USD)VRBO
From $130 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 $130 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 $653 per night (USD)VRBO
Rockport direct Waterfront 3 bedroom, 3 bathroom home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Breakwater House is a spacious contemporary home offering direct waterfront location in quiet, residential Pigeon Cove n ...
From $653 per night (USD)VRBO
From $1362 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 $1362 per night (USD)VRBO
From $527 per night (USD)Expedia
Long Beach Gloucester 2 minute walk to Beach.Large yard & lush gardens. Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The weeks of July 19 - 26 and August 16 - 23 have just opened up! This is your chance to enjoy Long Beach, only a few ...
From $527 per night (USD)Expedia
From $271 per night (USD)VRBO
\"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 $271 per night (USD)VRBO
From $391 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 $391 per night (USD)VRBO
From $473 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 $473 per night (USD)VRBO
From $1063 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 $1063 per night (USD)VRBO
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 $469 per night (USD)Expedia
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)Expedia
From $525 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 $525 per night (USD)VRBO
From $461 per night (USD)Expedia
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 ...
From $461 per night (USD)Expedia
From $224 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 $224 per night (USD)VRBO
From $352 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 $352 per night (USD)Expedia
From $631 per night (USD)VRBO
Harbortown Hideaway: Charming home in downtown Gloucester with water views.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Gloucester's Harbortown neighborhood, the name Harbortown Hideaway perfectly suits this vacation rental. A ch ...
From $631 per night (USD)VRBO
From $670 per night (USD)Expedia
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 $670 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 $342 per night (USD)Expedia
Historic charm meets contemporary comfort at Pigeon Hill.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Steeped in history, this traditional early victorian home has been newly remodeled and renovated blending original detai ...
From $342 per night (USD)Expedia
From $200 per night (USD)VRBO
Artist's Studio turned Guest House Sleeps up to 3
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
One room guest house with French doors leading to spacious deck, ocean views, less than 1/2 mile walk to Back Beach, vau ...
From $200 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 $221 per night (USD)VRBO
Come home to Rockport!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Spend a weekend or a week enjoying the beauty and culture of Rockport. Enjoy panoramic views of Sandy Bay.and Straights ...
From $221 per night (USD)VRBO
From $884 per night (USD)Expedia
Sunrise on the Cove: Unobstructed 180 degree views of Pigeon Cove.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
From its waterfront perch, this vacation rental home overlooks Rockport's picturesque Pigeon Cove harbor and has spectac ...
From $884 per night (USD)Expedia
From $437 per night (USD)VRBO
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 $437 per night (USD)VRBO
From $617 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 $617 per night (USD)VRBO
From $320 per night (USD)VRBO
Quaint getaway with full kitchen and lush yard - close to the beach and downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Vintage Rockport Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $320 per night (USD)VRBO
From $445 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 $445 per night (USD)Expedia
From $367 per night (USD)VRBO
Oceanfront home right on Long Beach near town & whale watching with tennis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Oceanfront Cottage - Long Beach Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $367 per night (USD)VRBO
From $680 per night (USD)Expedia
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 $680 per night (USD)Expedia
From $882 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 $882 per night (USD)VRBO
From $658 per night (USD)VRBO
Sweet, Bright, Water Views & 2 min walk to Beach Discounts available see below
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and make memories of a lifetime!! Easy living open floor plan, beachy bright and steps to Cape Hedge Beach and Long ...
From $658 per night (USD)VRBO
From $745 per night (USD)VRBO
Fantastic ocean views and 2 great beaches
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Ocean Crag has gorgeous ocean views and is located steps away from Cape Hedge and Long Beaches. Enjoy breathtaking view ...
From $745 per night (USD)VRBO
From $1118 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 $1118 per night (USD)VRBO
From $318 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 $318 per night (USD)VRBO
From $466 per night (USD)VRBO
Super cute Beachfront cottage, steps from beautiful sandy Long Beach
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
This 4 bedroom plus loft, 2 full bathroom cottage is only a few feet from the beautiful and sandy Long Beach in Rockport ...
From $466 per night (USD)VRBO
From $677 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 $677 per night (USD)VRBO
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 $227 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 $227 per night (USD)VRBO
From $386 per night (USD)Expedia
Sandy Bay: An oceanfront gem vacation rental with ocean views in Rockport.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to an oceanfront gem with exquisite views of Rockport's Sandy Bay and the Atlantic Ocean. Located just a short di ...
From $386 per night (USD)Expedia
From $969 per night (USD)VRBO
Landmark Lookout: Lovely views of Sandy Bay and the Atlantic Ocean.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy beautiful views of Sandy Bay and the Atlantic from this classic New England vacation rental home on Rockport's Pig ...
From $969 per night (USD)VRBO
From $726 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 $726 per night (USD)Expedia
From $562 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 $562 per night (USD)VRBO
From $584 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 $584 per night (USD)Expedia
From $594 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 $594 per night (USD)VRBO
From $447 per night (USD)Expedia
Granite Cottage: Charming cottage in Rockport with private deck and views.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From it's private deck, enjoy the views of Sandy Bay dotted with sailboats. Or, walk down the quiet lane to Granite Pier ...
From $447 per night (USD)Expedia
From $289 per night (USD)VRBO
You will love our location and will return for our hospitality!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
After the success of A Breezy Cottage, we set our sails on The Life of Reilly! The property was purchased in September, ...
From $289 per night (USD)VRBO
From $668 per night (USD)Expedia
Stay at Niles Beach S
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Summary: ✔ Great location: 3 min walk to Niles Beach ✔ 5 beds: king, queen, 3 twins (2 baths) ✔ Fully equipped kitchen ...
From $668 per night (USD)Expedia
From $402 per night (USD)VRBO
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 ...
From $402 per night (USD)VRBO
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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 ...
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From $798 per night (USD)VRBO
Sage Hill: Perfectly situated for Long Beach, Gloucester, and Rockport.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Midway between two picturesque places, the seaside village of Rockport and the historic fishing port of Gloucester, Sage ...
From $798 per night (USD)VRBO
From $826 per night (USD)Expedia
Granite Pier: Blends craftsmanship with modern amenities. Water views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Granite Pier, with its unparalleled ocean views, is a traditional Cape Ann home with an unusual history. Built in the mi ...
From $826 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 $353 per night (USD)VRBO
\"Absolutely lovely. The cottage, the beach, the town, the owners.\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A Breezy Cottage is a very short walk to the charming beaches of Rockport, MA. It comfortably sleeps up to 7 people inc ...
From $353 per night (USD)VRBO
From $661 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 $661 per night (USD)VRBO
From $856 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 $856 per night (USD)Expedia
From $747 per night (USD)VRBO
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 $747 per night (USD)VRBO
From $475 per night (USD)VRBO
The Harborview - Luxury 2 bedroom condo in Downtown Gloucester
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy a luxurious experience at this centrally-located condo in Downtown Gloucester. Newly built and finished home to a ...
From $475 per night (USD)VRBO
From $346 per night (USD)VRBO
Relax by the Sea – 3BR Rockport Retreat w\/ A\/C & Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Just an hour from Boston, this classic New England cottage puts you right in the heart of Rockport—and yes, it’s real (e ...
From $346 per night (USD)VRBO
From $607 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 $607 per night (USD)Expedia
From $406 per night (USD)VRBO
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 $406 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 $534 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 $534 per night (USD)VRBO
From $398 per night (USD)Expedia
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 $398 per night (USD)Expedia
From $162 per night (USD)VRBO
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 $162 per night (USD)VRBO
From $489 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 $489 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 $546 per night (USD)Expedia
Beach Bungalow: The perfect getaway to two of Rockport's finest beaches.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This sweet vacation rental cottage is a short distance to two of Rockport's finest beaches - Cape Hedge and Long Beach. ...
From $546 per night (USD)Expedia