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

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129 Holiday homes

Cape Ann holiday apartment rental

Essex apartment

1 bedroom / 1 bathroom / sleeps 4

1

from £154 / night

£964 - £1,271 / week

Home rental in Rockport

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

from £616 / night

£3,538 / week

Holiday b&b with golf nearby in Cape Ann

Essex b&b

1 bedroom / 1 bathroom / sleeps 3

from £142 / night

£989 / week

Cottage letting in Cape Ann

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

from £1,087 / night

£6,288 / week

Holiday apartment with golf nearby in Rockport

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 3

from £187 / night

£1,302 / week

Holiday home in Rockport

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

2

from £353 / night

£2,466 / week

Holiday home in Cape Ann

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

from £107 / night

£745 - £993 / week

Holiday cottage in Rockport

Rockport cottage

2 bedrooms / 2 bathrooms / sleeps 6

1

from £159 / night

£1,108 / week

Holiday cottage in Gloucester

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

1

Responds fast! avg. 1 hour 45 minutes

from £134 / night

£938 / week

Holiday cottage in Cape Ann

Rockport cottage

4 bedrooms / 1 bathroom / sleeps 7

from £354 / night

£1,894 / week

Cottage rental in Cape Ann

Rockport cottage

1 bedroom / 1 bathroom / sleeps 4

from £298 / night

£1,670 / week

Gloucester holiday home rental

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 10

2

from £475 / night

£3,323 / week

Home accommodation in Cape Ann

Essex house

6 bedrooms / 5 bathrooms / sleeps 14

from £1,562 / night

£9,116 / week

Cape Ann holiday apartment rental

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 4

1

from £170 / night

£1,107 - £1,350 / week

Holiday apartment in Cape Ann

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

3

from £95 / night

£662 / week

Cape Ann holiday home accommodation

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

from £644 / night

£4,402 / week

Holiday cottage letting

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 2

2

from £185 / night

£1,293 / week

Manchester-by-the-Sea holiday home rental

Manchester-by-the-Sea house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 11 minutes

from £323 / night

£2,261 / week

Holiday home in Rockport

Rockport house

3 bedrooms / 2 bathrooms / sleeps 8

from £601 / night

£3,424 / week

Gloucester holiday apartment rental

Gloucester apartment

2 bedrooms / 1 bathroom / sleeps 4

from £259 / night

£1,810 / week

Holiday home accommodation

Gloucester house

5 bedrooms / 3 bathrooms / sleeps 9

from £1,031 / night

£6,095 / week

Holiday cottage in Cape Ann

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 7

from £390 / night

£2,134 / week

Holiday home in Gloucester

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £643 / night

£4,015 / week

Gloucester holiday home rental

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

from £644 / night

£3,729 / week

Home rental in Gloucester

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

from £906 / night

£5,286 / week

Cape Ann holiday home rental

Rockport house

4 bedrooms / 2 bathrooms / sleeps 10

1

from £433 / night

£3,029 / week

Holiday b&b in Rockport

Rockport b&b

1 bedroom / 1 bathroom / sleeps 2

7

Responds fast! avg. 55 minutes

from £124 / night

£781 / week

Home rental in Cape Ann

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

1

from £300 / night

£1,621 / week

Holiday apartment in Gloucester

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

from £87 / night

£674 / week

Holiday apartment rental

Rockport apartment

1 bedroom / 1 bathroom / sleeps 2

1

from £185 / night

£1,294 / week

Gloucester holiday home rental

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 6

from £965 / night

£6,755 / week

Holiday home rental

Rockport house

4 bedrooms / 3 bathrooms / sleeps 7

from £460 / night

£2,615 / week

Holiday home in Cape Ann

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

from £846 / night

£5,104 / week

Holiday apartment in Cape Ann

Essex apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 42 minutes

from £153 / night

£1,065 / week

Holiday home in Cape Ann

Rockport house

4 bedrooms / 1 bathroom / sleeps 7

from £392 / night

£2,095 / week

Holiday b&b in Cape Ann

Rockport b&b

1 bedroom / 1 bathroom / sleeps 2

3

Responds fast! avg. 55 minutes

from £103 / night

£720 / week

Holiday home rental

Gloucester house

2 bedrooms / 1 bathroom / sleeps 6

from £318 / night

£1,710 / week

Holiday home in Cape Ann

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

from £92 / night

£642 - £1,487 / week

Holiday home in Gloucester

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

from £623 / night

£3,538 / week

Holiday b&b in Cape Ann

Essex b&b

1 bedroom / 1 bathroom / sleeps 4

from £151 / night

£1,055 / week

Viewing 40 of 129
rentals in Cape Ann

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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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