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114 houses
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Rockport house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$671
Golden Sands at Good Harbor: Across the street from the beach
Gloucester cottage
7 bedrooms / 3 bathrooms / sleeps 12
Price per night from
$1,723
GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
Rockport apartment
2 bedrooms / 1 bathroom / sleeps 3
Responds fast! avg. 2 hours 17 minutes
Price per night from
$281
Price per night from
$196
At the Footbridge entrance to Good Harbor Beach
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$655
Price per night from
$149
Granite Cottage: Charming cottage in Rockport with private deck and views
Rockport cottage
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$401
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Rockport cottage
2 bedrooms / 1 bathroom / sleeps 2
Responds fast! avg. 2 hours 17 minutes
Price per night from
$281
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$769
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Rockport cottage
4 bedrooms / 1 bathroom / sleeps 7
Price per night from
$550
Clamshell Landing: Bring your game to its squash & tennis courts!
Essex house
6 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$2,423
Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!
Gloucester apartment
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$361
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$1,369
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 6
Price per night from
$627
Seaside House: Good Harbor Beach and the Back Shore right outside your door.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$894
Granite Pier: Blends traditional craftsmanship with modern amenities. Views!
Rockport house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$1,004
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$1,021
Price per night from
$450
Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING
Rockport b&b
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 18 minutes
Price per night from
$184
Captain's Cottage: Traditional setting with a private footbridge to the beach
Rockport house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$459
LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
Rockport apartment
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 2 hours 17 minutes
Price per night from
$304
Price per night from
$138
SEASIDE GARDENS AFFORDABLE GUEST ROOM(S) IN VILLAGE BY BEACH, WALK EVERYWHERE!
Rockport b&b
1 bedroom / 1 bathroom / sleeps 2
Responds fast! avg. 18 minutes
Price per night from
$161
Sage Hill: Perfectly situated for Long Beach, Gloucester, and Rockport.
Rockport house
4 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$761
Sunset Cove: Waterfront home in Goose Cove section of Gloucester
Gloucester house
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$763
Long Beach House: Large, comfortable home just 285 feet from the white sands!
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$710
The Robert House: Explore Rockport and beyond from this historic home.
Rockport house
4 bedrooms / 1 bathroom / sleeps 7
Price per night from
$609
Price per night from
$1,167
Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches
Gloucester house
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$495
Price per night from
$950
Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.
Rockport house
5 bedrooms / 2 bathrooms / sleeps 9
Price per night from
$1,434
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf
Gloucester house
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 3 hours 38 minutes
Price per night from
$119
Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$982
Bell View: Private tennis court and an in-law suite.
Gloucester house
6 bedrooms / 5 bathrooms / sleeps 16
Price per night from
$1,694
Romantic SUMMERWIND COTTAGE- Scenic Harbor View
Gloucester cottage
2 bedrooms / 1 bathroom / sleeps 4
“Romantic Summerwind Cottage lives up to its name” We thoroughly enjoyed our stay in "Summerwind". It is a truly beautiful house. Linda and Hank, you did a wonderful job in remodeling and decorating the place. The color scheme and artwork reflect the lovely area and the lifestyle of Gloucester and we truly enjoyed the ambiance here. We felt very comfortable and welcomed in the house which was spotlessly clean and furnished with everything one could possibly need for their stay. We loved the area of East Gloucester. Good Harbor beach was a very enjoyable walk from the house. Rocky Neck and the Eastern Point Lighthouse were also very near and Rockport is only a short drive away. Our favorite restaurants were "My place by the Sea" in Rockport, "7th Wave " also in Rockport and "The Rudder" in Rocky Neck. We also enjoyed the beer at the Cape ann Brewing Company in Gloucester. And best of all was a barbecue on our veranda overlooking the Gloucester harbor. This was also where we enjoyed breakfast each morning watching the activity below. Linda, your exceptional taste and attention to detail made us choose Summerwind Cottage and we were not disappointed - it surpassed our expectations. A big thank you from Mira, Dominic and family (Ireland).
Responds fast! avg. 26 minutes
Price per night from
$321
Family Tides: Only a half-mile from Good Harbor Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$982
Viewing 38 of 114
rentals in Cape Ann
About Cape Ann
Cape Ann, Massachusetts
This rocky cape in Northeastern Massachusetts lies around 30 miles northeast of the city of Boston. Home to the historic port of Gloucester and pretty towns and villages including Rockport, Essex and Manchester-by-the-Sea, you’re sure to find your perfect seaside vacation property in Cape Ann with FlipKey.
About Cape Ann, Massachusetts
Cape Ann has a rich history, and Gloucester is one of the oldest towns in New England, founded in 1623. The town’s economy has relied on fishing for over 400 years, and wherever you go on the Cape, you’ll see fishing boats and creels – the seafood here is as fresh as it comes!
With its gorgeous, white sandy beaches, watersports, fishing and whale watching, a vacation on Cape Ann has something to offer everyone, from families to couples looking for a romantic retreat away from the hustle and bustle of Boston.
While you’re here, don’t miss out on a trip to Essex, the Home of the Fried Clam. Dipped in milk and flour, deep-fried and served with tartar sauce, these are a local specialty you simply have to try!
What to do in Cape Ann, Massachusetts
Spend your days relaxing on one of Cape Ann’s beautiful beaches. The soft white sands of Good Harbor ensure it’s a popular choice, whilst Front Beach (Rockport) is great for swimming and Singing Beach (Manchester-by-the-Sea) is a hidden gem!
Explore the historic town of Gloucester, home to America’s oldest seaport. Take a self-guided tour of the Gloucester Harbor Walk with its 42 story markers highlighting local history and culture, or visit one of the five lighthouses dotted along the coastline.
Visit the Shipbuilding Museum in Essex for a fascinating insight into the shipbuilding industry that once put this town on the map, or shop for antiques in the town center. Or head for Manchester-by-the-Sea, when the Festival by the Sea takes place every July. This colorful celebration of local art, culture, music and food is fun for the whole family.
Top travel tips for Cape Ann
If you’re flying to Cape Ann, the nearest airport is Boston Logan International, just 42 miles from the center of Gloucester.
Come in the summer months if you want to enjoy whale watching tours. Cape Ann is located midway between two whale feeding grounds where you can also spot dolphins and sea birds.
With average temperatures of 75 degrees Fahrenheit in July and August, summer is the best time to visit, although spring in Cape Ann is also quite warm and sunny.
With white sandy beaches, a rich seafaring history and some of the freshest seafood around, a vacation to Cape Ann can be a relaxing or activity-packed as you want it to be. Why not browse FlipKey’s range of vacation rentals for your perfect property in Rockport, Gloucester or Essex today?
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