Vacation Rentals & Houses in Cape Ann

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The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.

Rockport house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$544

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

Gloucester cottage

7 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$1,169

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

Rockport apartment

2 bedrooms / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 17 minutes

Price per night from

$281

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$196

Back Beach

Rockport house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$492

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$655

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$149

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

Rockport cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$288

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Rockport cottage

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 17 minutes

Price per night from

$281

Salt Island Views: Walking distance to Good Harbor & Long Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$648

Happy Days Cottage: Charming Folly Cove house with waterfront deck

Rockport cottage

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$398

Clamshell Landing: Bring your game to its squash & tennis courts!

Essex house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$1,702

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

$331

Annisquam Singing Pines: Private riverfront setting & tidal dock.

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$988

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

Gloucester cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$449

Seaside House: Good Harbor Beach and the Back Shore right outside your door.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$858

Granite Pier: Blends traditional craftsmanship with modern amenities. Views!

Rockport house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$685

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$692

The Cottage

Manchester-by-the-Sea house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$450

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Rockport b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$184

Captain's Cottage: Traditional setting with a private footbridge to the beach

Rockport house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$365

LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN

Rockport apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 17 minutes

Price per night from

$304

Coastal, Cute & Cozy|Close to Everything

Gloucester apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$160

Price per night from

$161

Sage Hill: Perfectly situated for Long Beach, Gloucester, and Rockport.

Rockport house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$533

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$531

Long Beach House: Large, comfortable home just 285 feet from the white sands!

Gloucester house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$694

The Robert House: Explore Rockport and beyond from this historic home.

Rockport house

4 bedrooms / 1 bathroom / sleeps 7

Price per night from

$441

Magnolia Tides: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$869

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

Gloucester house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$359

Beach & King Street Inn / Beach House Rental

Rockport house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$950

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

Rockport house

5 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$966

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, golf

Gloucester house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 13 minutes

Price per night from

$118

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

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$692

Bell View: Private tennis court and an in-law suite.

Gloucester house

6 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$1,164

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

Gloucester cottage

2 bedrooms / 1 bathroom / sleeps 4

“Gorgeous in every way” The cottage is tasteful, beautiful, comfortable and convenient. The views of the wonderful working harbor are breathtaking. The sunsets, seen from the deck while relaxing, dining, drinking coffee or something else are singularly spectacular. The color scheme in the cottage, the attention to detail, the artwork - all conspire to make the entire experience of being there as relaxing and enjoyable as it could possibly be. I would recommend Summerwind Cottage to anyone. I hope to return regularly. On top of all its other charms, the owners-Hank and Linda-are delightful people that I would love to see again under any circumstances.

Responds fast! avg. 27 minutes

Price per night from

$321

Family Tides: Only a half-mile from Good Harbor Beach.

Gloucester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$675

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

Rockport cottage

1 bedroom / 1 bathroom / sleeps 2

“An Oasis By The Sea” August 30, 2012 Dear Rose & Guy- Thank you very, very much for our wonderful stay at Periwinkle Cottage! From the beautifully decorated rooms, the most comfortable beds, soft luxurious towels and linens, convenient kitchen, TV to the lovely outdoor sitting area and garden... Omg...what a gem! It is a true delight! And the cottage is immaculate and very peaceful and tranquil. We will definitely recommend your "oasis by the sea" to our family and friends! Love, Penny and Urs Westport, Connecticut

Responds fast! avg. 21 minutes

Price per night from

$195

Viewing 38 of 116
rentals in Cape Ann

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About Cape Ann

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?

Top Destination reviews

Beach & King Street Inn / Beach House Rental
Paradise on a beautiful shoreline...Found!

I have been staying at the Beach & King for 4 years and counting! The location-outstanding. Front Beach and Rockport shops, restaurants and galleries are all right there. The house and decor is contemporary, artistic, spotless and everything you would ever need has been considered . There are 5 bathrooms and it is such a luxury when traveling with a group. Owners are available if needed, but hands off during your stay. Highly recommend! But not during my week ;) … see more
GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
Vacation

We had a very enjoyable time. Our rooms were cozy and clean and way more comfortable than a regular hotel. The owner was very nice … see more
Romantic SUMMERWIND COTTAGE- Scenic Harbor View
A Perfect Gloucester Setting

My wife and I stayed a week at Summerwind in September. The house overlooks Gloucester harbor, and although close to the center of town and near restaurants and shops, it is situated on a hillside off a quiet side street. The cottage itself is airy and beautifully furnished with an attractive color scheme, and some paintings. it is not cluttered with bricabrak and other cutsey things one might find in a rental. I have built a few of the houses I have lived in and can say that the structure, workmanship, and finishing of Summerwind is exceptional. The kitchen and bath are fully fitted out and all the fixtures are new. Kitchen needs, like paper towels, spices, and condiments were well present. Mattresses are of good quality and there is plenty of bed linens, blankets, and towels.The ample deck is a great place for sunsets and evening dining. Linda amero is a charming and helpful landlady - without being intrusive. She lives next door, and let us know right off she was always available to help with finding supermarkets and places of interest. There is a printed sheet of instructions that made our stay easy. There is also Wifi and a large screen TV with cable. We would give it ten stars if we could. I know we will be back to Gloucester and Summerwind. Frank O'Brien Roanoke, Virginia … see more
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet
Peaceful cottage getaway

Had a great time here. Love the outdoor set up! Bathroom a tad small but functions great. Dvd player didn't work. The place has a lot of extras and is very cozy. Great romantic spot to stay. … see more
Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING
Perfect location for a relaxing vacation

We come every year! It's a wonderful homey place- attractive, clean and convenient to everything. We don't even need a car when we come. This year we used the top floor guest rooms to spread out, and it was wonderful to have the extra space and privacy for everyone in the group. The living room is perfect for hanging out and watching a movie, and the fridge upstairs was very convenient for keeping cold drinks and leftovers on hand for those lazy evenings. The front porch is great for people watching while having a glass of wine at the end of the day. We'll be back here every summer! … see more
Back Beach
Great house in a great location!

Fabulously comfortable house. Nicely done, nicely appointed, nicely equipped. The owner was gracious, accommodating and informative. She met us at the house, provided a tour and the "workings of the house" as well as local information. The location was perfect if you're looking for a small town atmosphere with all the amenities. There was a bit more traffic than I thought there would be, but the comfort level of the house outweighed any inconvenience. The town was charming, walkable. Commuting to surrounding areas such as Boston, Salem, and Portsmouth was easy both by car and train. Overall, a wonderful experience. Thank you Mary, for a enjoyable, relaxing stay. … see more

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