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Cape Ann Rentals

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Cape Ann Rentals

About Cape Ann

144 houses

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

Essex apartment

1 bedroom / 1 bathroom / Sleeps 4

$175

1 / 6

Gloucester Harborscape View 1 & 1/2 BR; walk to beach & town

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 5

Responds fast! avg. 3 hours 13 minutes

$110

1 / 46

Cozy Rockport Cottage with Ocean Views

Rockport cottage

2 bedrooms / 1 bathroom / Sleeps 5

$180

1 / 14

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$175

1 / 14

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 13

$429

1 / 17

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / Sleeps 2

$165

1 / 11

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 45 minutes

$169

1 / 18

Sage Hill: Easy access to both Gloucester & Rockport

Rockport house

4 bedrooms / 3 bathrooms / Sleeps 7

$290

1 / 23

The Sail Loft of Bearskin Neck

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 1 hour 56 minutes

$155

1 / 15

Beach Stone Cottage: Just feet from the white sands of Good Harbor Beach

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$640

1 / 24

Lovely 'Blue Heron Cottage' on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 6

Responds fast! avg. 23 minutes

$199

1 / 24

Wingaersheek beach private side 3 level treetop cottage house w/ 4 bedrooms

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 10 minutes

$300

1 / 23

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

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 7

$261

1 / 26

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

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 1 minutes

$89

1 / 37

Rockport Beach Escape: Stroll to Old Garden Beach or town.

Rockport house

5 bedrooms / 3 bathrooms / Sleeps 12

$772

1 / 22

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / Sleeps 11

Responds fast! avg. 3 hours 13 minutes

$500

1 / 7

Granite Pier: Blends traditional craftsmanship with modern amenities.

Rockport house

3 bedrooms / 2 bathrooms / Sleeps 8

$550

1 / 23

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

Gloucester house

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 1 hour 1 minutes

$65

1 / 28

Second Floor: 2+ Bedroom, 1.25 Bath

Manchester-by-the-Sea condo

3 bedrooms / 1 bathroom / Sleeps 5

$250

1 / 16

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$197

1 / 20

Quaint Seaside Village Studio Steps From Beach

Rockport b and b

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 1 hour 36 minutes

$125

1 / 12

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

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 7

$153

1 / 21

Beach Walk: Good Harbor Beach footbridge just steps away!

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$238

1 / 11

Vintage Home directly on the Annisquam River

Gloucester house

6 bedrooms / 3 bathrooms / Sleeps 12

Responds fast! avg. 3 hours 18 minutes

$314

1 / 12

Rockport Hideaway: Private pool & a short walk to all Rockport has to offer.

Rockport house

3 bedrooms / 2 bathrooms / Sleeps 6

$376

1 / 21

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / Sleeps 7

$397

1 / 19

Helena House: European flair, close to Plum Cove Beach.

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 7

$183

1 / 21

Captain Quarters

Rockport b and b

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 2 hours 48 minutes

$160

1 / 14

Point de Chene: Direct waterfront historic home with incredible views

Rockport house

5 bedrooms / 3 bathrooms / Sleeps 12

$719

1 / 36

Granite Courtyard: Charming cottage in Rockport with private deck and views

Rockport cottage

1 bedroom / 1 bathroom / Sleeps 4

$230

1 / 16

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / Sleeps 4

$40

1 / 11

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

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 45 minutes

$182

1 / 18

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

Gloucester house

3 bedrooms / 3 bathrooms / Sleeps 8

$450

1 / 33

A Year-Round Vacation Home

Rockport house

3 bedrooms / 2 bathrooms / Sleeps 5

Responds fast! avg. 3 hours 23 minutes

$250

1 / 15

4 Bedroom Cottage on the Beach!

Rockport house

4 bedrooms / 1 bathroom / Sleeps 7

“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

$350

1 / 17

Sea Fox: Custom-designed home with rights to private Coffins Beach

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$390

1 / 23

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

Rockport house

6 bedrooms / 3 bathrooms / Sleeps 10

$376

1 / 31

Rosemarc House: 180-degree ocean views & a private beach

Gloucester house

3 bedrooms / 3 bathrooms / Sleeps 6

$1,433

1 / 33
Viewing 38 of 144

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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