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Vacation Rentals & Houses in Cape Ann

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Vacation Rentals & Houses in Cape Ann

About Cape Ann

194 houses

Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet

Rockport cottage

1 bedroom / 1 bathroom / sleeps 2

1 / 23

John Oakes Rockport Harbor House: Historical home right on the water

Rockport house

3 bedrooms / 1 bathroom / sleeps 6

1 / 32

Family Friendly Apartment, Short Walk to Beach/Downtown, Parking, WiFi, Grill

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 7

1 / 21

Inviting apartment with harbor views, fireplace, patio, & gas grill!

Gloucester house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 31 minutes

1 / 28

Oceans Views And Minutes Walk To Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

1 / 26

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 16 minutes

1 / 26

One Bedroom Loft Apartment B at Cedar Hill Farm B & B

Essex apartment

1 bedroom / 1 bathroom / sleeps 4

1 / 6

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 31 minutes

1 / 37

The Sail Loft of Bearskin Neck

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

1 / 17

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Rockport b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 29 minutes

1 / 12

Cozy Rockport Cottage with Ocean Views

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 5

1 / 14

Landfall, 5 br/3 bath a welcoming respite after a journey from land or sea.

Rockport house

5 bedrooms / 3 bathrooms / sleeps 10

1 / 23

Meet Me On South Street: Walk to Rockport's village and beaches.

Rockport condo

2 bedrooms / 2 bathrooms / sleeps 4

1 / 20

Booth Cottage

Manchester-by-the-Sea house

4 bedrooms / 4 bathrooms / sleeps 10

1 / 4

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 49 minutes

1 / 27

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

1 / 11

Water's Edge: Direct waterfront on picturesque Goose Cove with dock

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

1 / 33

The Robert House: 4 bedroom Rockport village house, sleeps 7

Rockport house

4 bedrooms / 1 bathroom / sleeps 7

1 / 25

The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

1 / 29

40% off regular rate: Wonderful 4 Bedroom, 2 Full Bath Restored 1917 Home

Manchester-by-the-Sea house

4 bedrooms / 2 bathrooms / sleeps 7

1 / 44

Happy Days Cottage: Charming Folly Cove house with waterfront deck

Rockport cottage

4 bedrooms / 1 bathroom / sleeps 7

1 / 28

Rockport Seaside Retreat: Walk to waterfront, town and beaches.

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

1 / 26

Captain Quarters

Rockport b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

1 / 14

The Friendship Room at Cedar Hill Farm B & B

Essex b and b

1 bedroom / 1 bathroom / sleeps 3

1 / 13

GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 37 minutes

1 / 18

Back Beach Cottages - Charming house & guest house

Rockport house

3 bedrooms / 3 bathrooms / sleeps 8

1 / 17

The Cable House: High-end oceanfront family home, 1/10 mi to Cape Hedge Beach

Rockport house

3 bedrooms / 2 bathrooms / sleeps 7

1 / 35

Mon Altre Cove House: Gather the family to this seaside retreat.

Rockport house

6 bedrooms / 3 bathrooms / sleeps 10

1 / 31

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 12

1 / 18

18th Century Cottage with attached guest suite

Rockport cottage

2 bedrooms / 2 bathrooms / sleeps 6

1 / 24

Second Floor: 2+ Bedroom, 1.25 Bath

Manchester-by-the-Sea condo

3 bedrooms / 1 bathroom / sleeps 5

1 / 16

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

1 / 15

Little Red House: Close to Gloucester's historic Stage Fort Park & beaches

Gloucester house

3 bedrooms / 1 bathroom / sleeps 5

1 / 19

Golden Sands at Good Harbor: Across the street from the beach

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

1 / 28

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

1 / 9

Straitsmouth Cove: Outstanding ocean views at Gap Head Cove in Rockport.

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

1 / 40

Boulevard Bungalow: Steps away from Gloucester's fabled Stacy Boulevard.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

1 / 26

4 Bedroom Cottage on the Beach!

Rockport house

4 bedrooms / 1 bathroom / sleeps 7

1 / 17
Viewing 38 of 194

About Cape Ann

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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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