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Vacation Rentals & Houses in Cape Ann

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Vacation Rentals & Houses in Cape Ann

About Cape Ann

207 houses

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$275

1 / 14

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

Essex apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$175

1 / 6

The Sail Loft of Bearskin Neck

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

Price per night from

$170

1 / 17

Lovely 'Blue Heron Cottage' on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 9 minutes

Price per night from

$199

1 / 24

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

Price per night from

$400

1 / 17

Second Floor: 2+ Bedroom, 1.25 Bath

Manchester-by-the-Sea condo

3 bedrooms / 1 bathroom / sleeps 5

Price per night from

$250

1 / 16

Sea Vagabond: Amazing water views & close to Long Beach

Rockport house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$245

1 / 21

Long Beach Place: Just steps from the white sand & surf.

Gloucester apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$390

1 / 25

Quaint Seaside Village Studio Steps From Beach

Rockport b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 32 minutes

Price per night from

$125

1 / 12

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 35 minutes

Price per night from

$136

1 / 37

Captain Quarters

Rockport b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 8 minutes

Price per night from

$160

1 / 14

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 26 minutes

Price per night from

$429

1 / 15

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$115

1 / 26

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

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$390

1 / 23

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 1 hour 0 minutes

Price per night from

$500

1 / 7

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

Gloucester house

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 35 minutes

Price per night from

$81

1 / 28

Two Beaches: Walk to Long Beach or Good Harbor!

Gloucester house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$283

1 / 27

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$940

1 / 57

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

$197

1 / 20

Test Property- TA Test

Gloucester cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$12

1 / 4

Beautiful First Floor 2 BR Condo in Manchester

Manchester-by-the-Sea townhouse

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$214

1 / 15

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / sleeps 2

Price per night from

$165

1 / 11

Treehouse by the Sea: Stacy Boulevard, Downtown Gloucester, and Beaches

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$240

1 / 21

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

Rockport house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$772

1 / 22

Stunning Views - Spacious Home

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$500

1 / 39

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 6

“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

Responds fast! avg. 2 hours 37 minutes

Price per night from

$240

1 / 26

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

Price per night from

$110

1 / 46

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

Rockport condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$280

1 / 20

18th Century Cottage with attached guest suite

Rockport cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$186

1 / 24

Periwinkle Cottage - Unit 1

Rockport cottage

1 bedroom / 1 bathroom / sleeps 2

“It was very peaceful and welcoming.” Forgot your toothbrush? Don't worry, there's one there. Forgot your shaving cream? Again, not to worry. Rosemarie provided all that was needed and more. We prefer to cook our own breakfast and found that all th

Price per night from

$125

1 / 23

The Friendship Room at Cedar Hill Farm B & B

Essex b and b

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$150

1 / 13

Granite Pier: Blends traditional craftsmanship with modern amenities.

Rockport house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$550

1 / 23

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$143

1 / 11

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$325

1 / 26

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

Gloucester house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$450

1 / 33

Thurston Point: Waterfront rental with deepwater dock on Annisquam River!

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

Price per night from

$304

1 / 29

A Year-Round Vacation Home

Rockport house

3 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 22 minutes

Price per night from

$250

1 / 15

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

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$610

1 / 40
Viewing 38 of 207

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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