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Cottages in Cape Ann and Apartments - Holiday Lettings - Holiday Rentals Cape Ann

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117 Holiday homes

Home rental in Rockport

Rockport house

4 bedrooms • 2 bathrooms • sleeps 7

from £507 / night

£2,805 / week

1 / 29

Cottage letting in Cape Ann

Gloucester cottage

7 bedrooms • 3 bathrooms • sleeps 12

from £1,306 / night

£7,596 / week

1 / 31

Holiday apartment with golf nearby in Rockport

Rockport apartment

2 bedrooms • 1 bathroom • sleeps 3

from £205 / night

£1,431 / week

1 / 18

Holiday home in Rockport

Rockport house

4 bedrooms • 2 bathrooms • sleeps 8

from £357 / night

£2,498 / week

1 / 15

Holiday home in Cape Ann

Rockport house

2 bedrooms • 1 bathroom • sleeps 4

from £107 / night

£750 - £999 / week

1 / 11

Holiday cottage in Gloucester

Gloucester cottage

3 bedrooms • 1 bathroom • sleeps 6

from £152 / night

£1,060 / week

1 / 29

Holiday cottage in Cape Ann

Rockport cottage

4 bedrooms • 1 bathroom • sleeps 7

from £414 / night

£2,253 / week

1 / 34

Cottage rental in Cape Ann

Rockport cottage

1 bedroom • 1 bathroom • sleeps 4

from £342 / night

£1,918 / week

1 / 17

Gloucester holiday home rental

Gloucester house

6 bedrooms • 2 bathrooms • sleeps 10

from £476 / night

£3,331 / week

1 / 18

Home accommodation in Cape Ann

Essex house

6 bedrooms • 5 bathrooms • sleeps 14

from £1,838 / night

£10,902 / week

1 / 46

Holiday apartment in Cape Ann

Gloucester apartment

1 bedroom • 1 bathroom • sleeps 3

from £96 / night

£671 / week

1 / 26

Cape Ann holiday home accommodation

Gloucester house

4 bedrooms • 2 bathrooms • sleeps 10

from £775 / night

£5,197 / week

1 / 44

Holiday cottage letting

Rockport cottage

2 bedrooms • 1 bathroom • sleeps 2

from £205 / night

£1,435 / week

1 / 18

Manchester-by-the-Sea holiday home rental

Manchester-by-the-Sea house

3 bedrooms • 2 bathrooms • sleeps 6

from £327 / night

£2,290 / week

1 / 17

Holiday home in Rockport

Rockport house

3 bedrooms • 2 bathrooms • sleeps 8

from £778 / night

£4,503 / week

1 / 39

Gloucester holiday apartment rental

Gloucester apartment

2 bedrooms • 1 bathroom • sleeps 4

from £307 / night

£2,098 / week

1 / 16

Holiday home accommodation

Gloucester house

5 bedrooms • 3 bathrooms • sleeps 9

from £1,209 / night

£7,146 / week

1 / 24

Holiday cottage in Cape Ann

Gloucester cottage

3 bedrooms • 1 bathroom • sleeps 7

from £475 / night

£2,606 / week

1 / 29

Holiday home in Gloucester

Gloucester house

3 bedrooms • 2 bathrooms • sleeps 8

from £687 / night

£4,866 / week

1 / 20

Gloucester holiday home rental

Gloucester house

4 bedrooms • 2 bathrooms • sleeps 7

from £772 / night

£4,460 / week

1 / 33

Home rental in Gloucester

Gloucester house

5 bedrooms • 2 bathrooms • sleeps 10

from £1,009 / night

£5,803 / week

1 / 49

Cape Ann holiday home rental

Rockport house

4 bedrooms • 2 bathrooms • sleeps 10

from £303 / night

£3,802 / week

1 / 27

Holiday b&b in Rockport

Rockport b&b

1 bedroom • 1 bathroom • sleeps 2

from £134 / night

£933 / week

1 / 12

Home rental in Cape Ann

Rockport house

2 bedrooms • 1 bathroom • sleeps 4

from £337 / night

£1,836 / week

1 / 22

Holiday apartment in Gloucester

Gloucester apartment

1 bedroom • 1 bathroom • sleeps 2

from £83 / night

£641 / week

1 / 9

Holiday apartment rental

Rockport apartment

1 bedroom • 1 bathroom • sleeps 2

from £222 / night

£1,552 / week

1 / 19

Gloucester holiday home rental

Gloucester house

4 bedrooms • 3 bathrooms • sleeps 6

from £1,030 / night

£7,111 / week

1 / 49

Holiday home rental

Rockport house

4 bedrooms • 3 bathrooms • sleeps 6

from £575 / night

£3,234 / week

1 / 39

Holiday home in Cape Ann

Rockport house

5 bedrooms • 2 bathrooms • sleeps 9

from £1,061 / night

£6,203 / week

1 / 35

Holiday home in Cape Ann

Rockport house

4 bedrooms • 1 bathroom • sleeps 7

from £459 / night

£2,497 / week

1 / 34

Holiday b&b in Cape Ann

Rockport b&b

1 bedroom • 1 bathroom • sleeps 2

from £117 / night

£816 / week

1 / 15

Holiday home rental

Gloucester house

2 bedrooms • 1 bathroom • sleeps 6

from £373 / night

£2,041 / week

1 / 22

Holiday home in Cape Ann

Gloucester house

2 bedrooms • 1 bathroom • sleeps 4

from £89 / night

£615 - £1,496 / week

1 / 35

Holiday home in Gloucester

Gloucester house

3 bedrooms • 2 bathrooms • sleeps 8

from £743 / night

£4,261 / week

1 / 28

Gloucester holiday home rental

Gloucester house

2 bedrooms • 2 bathrooms • sleeps 6

from £640 / night

£3,666 / week

1 / 36

Cape Ann holiday home rental

Gloucester house

3 bedrooms • 2 bathrooms • sleeps 6

from £743 / night

£4,252 / week

1 / 33

Cottage rental in Gloucester

Gloucester cottage

2 bedrooms • 1 bathroom • sleeps 6

“Excellent staty!” Excellent cottage. Everything was as promised. Had a very minor issue, which was immediately resolved by Linda. Loved the area and having a great place to stay made the trip even more memorable.

from £250 / night

£1,574 - £1,690 / week

1 / 31

Home rental in Cape Ann

Gloucester house

5 bedrooms • 2 bathrooms • sleeps 10

from £552 / night

£3,706 / week

1 / 20

Holiday home in Gloucester

Gloucester house

2 bedrooms • 1 bathroom • sleeps 4

from £312 / night

£2,183 / week

1 / 12

Holiday home in Gloucester

Gloucester house

6 bedrooms • 5 bathrooms • sleeps 16

from £1,287 / night

£7,350 / week

1 / 53

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Cape Ann holidays

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 holiday property in Cape Ann with Holiday Lettings.

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 holiday 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 speciality 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 Harbour 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 Harbour 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 centre. Or head for Manchester-by-the-Sea, when the Festival by the Sea takes place every July. This colourful 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 centre 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 holiday to Cape Ann can be a relaxing or activity-packed as you want it to be. Why not browse Holiday Lettings’s range of holiday rentals for your perfect property in Rockport, Gloucester or Essex today?

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