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179 houses
One Bedroom Loft Apartment B at Cedar Hill Farm B & B
Essex apartment
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$205
Wonderful 5 Bedroom, 3 Full Bath, Meticulous
Manchester-by-the-Sea house
5 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$468
Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$513
Price per night from
$176
The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.
Rockport house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$939
Golden Sands at Good Harbor: Across the street from the beach
Gloucester cottage
7 bedrooms / 3 bathrooms / sleeps 12
Price per night from
$1,406
GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
Rockport apartment
2 bedrooms / 1 bathroom / sleeps 3
Price per night from
$251
Price per night from
$166
Beautiful First Floor 2 BR Condo in Manchester
Manchester-by-the-Sea townhouse
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$251
Price per night from
$495
Lovely 'Blue Heron Cottage' on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 6
Responds fast! avg. 4 minutes
Price per night from
$236
Price per night from
$218
Price per night from
$335
Price per night from
$367
At the Footbridge entrance to Good Harbor Beach
Gloucester house
6 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$668
Price per night from
$135
Price per night from
$211
Poolside Summers: Swim in the private in-ground pool or walk to the beach
Rockport house
4 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$711
The Sail Loft of Bearskin Neck- Old Harbor Retreat
Rockport apartment
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$229
Granite Cottage: Charming cottage in Rockport with private deck and views
Rockport cottage
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$377
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Rockport cottage
2 bedrooms / 1 bathroom / sleeps 2
Price per night from
$248
Salt Island Views: Walking distance to Good Harbor & Long Beach.
Gloucester house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$728
Happy Days Cottage: Charming Folly Cove house with waterfront deck
Rockport cottage
4 bedrooms / 1 bathroom / sleeps 7
Price per night from
$443
Oceanside at Good Harbor: Walk 0.2 mi to the white sands of Good Harbor Beach
Gloucester house
5 bedrooms / 3 bathrooms / sleeps 9
Price per night from
$1,193
Clamshell Landing: Bring your game to its squash & tennis courts!
Essex house
6 bedrooms / 5 bathrooms / sleeps 14
Price per night from
$1,992
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
$285
Annisquam Singing Pines: Private riverfront setting & tidal dock.
Gloucester house
5 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$1,169
Quarry Crest House: Includes swimming rights to Little Parker quarry
Rockport house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$501
Thurston Point: Waterfront rental with deepwater dock on Annisquam River!
Gloucester cottage
3 bedrooms / 1 bathroom / sleeps 7
Price per night from
$501
Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown
Rockport house
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 16 minutes
Price per night from
$169
Tuller House, a tranquil retreat on Rockport's "the Avenues."
Rockport house
3 bedrooms / 1 bathroom / sleeps 5
Price per night from
$477
Seaside House: Good Harbor Beach and the Back Shore right outside
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$778
Granite Pier: Blends traditional craftsmanship with modern amenities. Views!
Rockport house
3 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$725
Perrywinkle: Waterfront on Gloucester’s Rocky Neck.
Gloucester house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$854
The Cable House: High-end oceanfront family home, 1/10 mi to Cape Hedge Beach
Rockport house
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$1,060
Back Beach Cottages - Charming house & guest house
Rockport house
3 bedrooms / 3 bathrooms / sleeps 8
Price per night from
$530
“a little bit of heaven” My family and I have rented the cottage for 2 weeks for several years. Friends who come for the first time are speechless when they see the view. This is a wonderful place for children and grandchildren. Little ones run free into the surf or fish for crabs at the footbridge using hotdogs for bait. To see the sunrise over the breakwater is breathtaking. To see the full moon reflected on the crashing waves at night is a sight to behold. Downtown Rockport is just a 5 minute ride down the road. Grocery stores nearby, convenient to rt. 128 and several restaurants in Gloucester and Rockport. This is everything you would want and need for a seaside getaway.
Price per night from
$594
Viewing 38 of 179
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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