Vacation Rentals & Houses in Cape Ann

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

203 houses

(1) Excellent 

6

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

Cape Ann / Essex

Essex apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$201

Price per night from

$201

26

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

Cape Ann / Gloucester

Gloucester house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Ask about children

Price per night from

$328

Price per night from

$328

13

The Friendship Room at Cedar Hill Farm B & B

Cape Ann / Essex

Essex b and b

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$172

Price per night from

$172

15

Beautiful First Floor 2 BR Condo in Manchester

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea townhouse

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$245

Price per night from

$245

16

Second Floor: 2+ Bedroom, 1.25 Bath

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea condo

3 5 4 nights min

  • 3 bedrooms
  • sleeps 5
  • 4 nights min
  • Child Friendly

Price per night from

$287

Price per night from

$287

44

40% off regular rate: Wonderful 4 Bedroom, 2 Full Bath Restored 1917 Home

Cape Ann / Manchester-by-the-Sea

Manchester-by-the-Sea house

4 7 5 nights min

  • 4 bedrooms
  • sleeps 7
  • 5 nights min
  • Child Friendly

Price per night from

$458

Price per night from

$458

29

The Rockporter: Enjoy beautiful views of Pigeon Cove Harbor.

Cape Ann / Rockport

Rockport house

4 7 3 nights min

  • 4 bedrooms
  • sleeps 7
  • 3 nights min
  • Ask about children

Price per night from

$513

Price per night from

$513

(6) Excellent 

14

Waterfront 2 Bedroom !

Cape Ann / Gloucester

Gloucester apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$172

Price per night from

$172

(5) Excellent 

21

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

Cape Ann / Rockport

Rockport apartment

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Child Friendly

Price per night from

$228

Price per night from

$228

(2) Very Good 

12

Beachcomber Suite

Cape Ann / Rockport

Rockport house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden

Price per night from

$201

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$201

28

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

Cape Ann / Gloucester

Gloucester cottage

7 12 min stay varies

  • 7 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children

Price per night from

$1,013

Price per night from

$1,013

18

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

Cape Ann / Rockport

Rockport apartment

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$245

Responds fast!
avg. 37 minutes

Price per night from

$245

(1) Excellent 

24

Lovely 'Blue Heron Cottage' on Annisquam River!

Cape Ann / Gloucester

Gloucester cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$228

Responds fast!
avg. 7 minutes

Price per night from

$228

(1) Excellent 

12

Waterfront Woodsy 3BR Cottage

Cape Ann / Gloucester

Gloucester house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$213

Price per night from

$213

26

Oceans Views And Minutes Walk To Beach

Cape Ann / Rockport

Rockport house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$328

Price per night from

$328

(2) Excellent 

15

Back Beach

Cape Ann / Rockport

Rockport house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$492

Responds fast!
avg. 1 hour 46 minutes

Price per night from

$492

(1) Excellent 

24

18th Century Cottage with attached guest suite

Cape Ann / Rockport

Rockport cottage

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$213

Price per night from

$213

23

North Seas Cottage: Water views in serene Pigeon Cove

Cape Ann / Rockport

Rockport cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$266

Price per night from

$266

39

Stunning Views - Spacious Home

Cape Ann / Gloucester

Gloucester house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi

Price per night from

$573

Price per night from

$573

(4) Excellent 

14

Captain Quarters

Cape Ann / Rockport

Rockport b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning

Price per night from

$184

Responds fast!
avg. 2 hours 22 minutes

Price per night from

$184

28

Happy Days Cottage: Charming Folly Cove house with waterfront deck

Cape Ann / Rockport

Rockport cottage

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$313

Price per night from

$313

14

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

Cape Ann / Rockport

Rockport cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$253

Price per night from

$253

7

Fabulous Waterfront 2 Bedroom - Boat dock option

Cape Ann / Gloucester

Gloucester apartment

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Ask about pets

Price per night from

$77

Price per night from

$77

28

NEW LISTING! Quaint getaway w/ kitchen & lush yard - near beach & town, dogs OK!

Cape Ann / Rockport

Rockport house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$111

Price per night from

$111

12

Rockport cottage walking distance in town beaches Bearskin Neck Shalin Liu train

Cape Ann / Rockport

Rockport cottage

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$178

Responds fast!
avg. 3 hours 38 minutes

Price per night from

$178

33

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

Cape Ann / Gloucester

Gloucester house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$453

Price per night from

$453

(2) Very Good 

18

At the Footbridge entrance to Good Harbor Beach

Cape Ann / Gloucester

Gloucester house

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Private garden

Price per night from

$654

Price per night from

$654

(10) Excellent 

40

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

Cape Ann / Gloucester

Gloucester apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Child Friendly

Price per night from

$138

Price per night from

$138

21

Poolside Summers: Swim in the private in-ground pool or walk to the beach

Cape Ann / Rockport

Rockport house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$463

Price per night from

$463

30

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

Cape Ann / Essex

Essex house

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Ask about children
  • Air conditioning

Price per night from

$1,313

Price per night from

$1,313

(1) Excellent 

14

Cozy Rockport Cottage with Ocean Views

Cape Ann / Rockport

Rockport cottage

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly

Price per night from

$206

Price per night from

$206

31

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Cape Ann / Gloucester

Gloucester house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$420

Price per night from

$420

31

Welcome Home: Walk to Gloucester's historic harbor and beaches.

Cape Ann / Gloucester

Gloucester house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children

Price per night from

$477

Price per night from

$477

28

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

Cape Ann / Gloucester

Gloucester house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$113

Price per night from

$113

(2) Excellent 

18

GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM

Cape Ann / Rockport

Rockport cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Child Friendly

Price per night from

$217

Responds fast!
avg. 37 minutes

Price per night from

$217

(3) Very Good 

26

Bohemia RETREAT Studio

Cape Ann / Gloucester

Gloucester apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Private garden

Price per night from

$132

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$132

20

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

Cape Ann / Rockport

Rockport condo

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Ask about children

Price per night from

$283

Price per night from

$283

(2) Very Good 

12

Vintage Home directly on the Annisquam River

Cape Ann / Gloucester

Gloucester house

6 12 4 nights min

  • 6 bedrooms
  • sleeps 12
  • 4 nights min
  • Beach / lakeside relaxation
  • Ask about pets

Price per night from

$360

Responds fast!
avg. 3 hours 49 minutes

Price per night from

$360

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?