Vacation Rentals

Cape Ann Vacation Rentals

Welcome to Cape Ann, the other cape of Massachusetts, where scenic beauty meets New England charm. Whether you’re seeking a cozy retreat in Gloucester, an artistic escape in Rockport, or a beachside getaway, our Cape Ann vacation rentals offer something for everyone.

69 results

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Two Beaches Cottage

Two Beaches Cottage

3 1.5 8 Gloucester

Sandy Bay

Sandy Bay

1 1.5 4 Rockport

Afternoon Delight

Afternoon Delight

3 2 6 Beverly

Annisquam River Sunsets

Annisquam River Sunsets

2 1 4 Gloucester

Annisquam Singing Pines

Annisquam Singing Pines

5 2 10 Gloucester

Beach Bungalow

Beach Bungalow

2 1 5 Rockport

Bell View

Bell View

6 5 16 Gloucester

Booth Cottage

Booth Cottage

4 3.5 8 Manchester-by-the-Sea

Changes In Latitude

Changes In Latitude

3 2 6 Gloucester

Folly Cove Cottage

Folly Cove Cottage

1 1.5 4 Rockport

Garden by the Sea

Garden by the Sea

2 1 4 Gloucester

Golden Sands

Golden Sands

7 3.5 12 Gloucester

Granite Cottage

Granite Cottage

1 1 4 Rockport

Granite Pier

Granite Pier

3 2 8 Rockport

Helena House

Helena House

3 2.5 7 Gloucester

Jewel Box

Jewel Box

2 1 3 Gloucester

Captain John Butman House

Captain John Butman House

3 2 6 Rockport

Joseph's Way

Joseph's Way

2 1 4 Gloucester

Landmark Lookout

Landmark Lookout

4 2 8 Rockport

Long Beach House

Long Beach House

5 2.5 10 Gloucester

Mill Lane

Mill Lane

1 1 3 Rockport

Over By Good Harbor

Over By Good Harbor

4 3.5 10 Gloucester

Perrywinkle

Perrywinkle

4 3 7 Gloucester

Pigeon Hill

Pigeon Hill

2 2 4 Rockport

Pleasant House in Rockport

Pleasant House in Rockport

4 4 10 Rockport

River's Edge

River's Edge

2 1.5 4 Gloucester

River Watch

River Watch

3 2 6 Gloucester

Ryal Side Hideaway Cove

Ryal Side Hideaway Cove

3 1 6 Beverly

Sage Hill

Sage Hill

3 3 6 Rockport

Salt Island Views

Salt Island Views

3 2 8 Gloucester

Seacroft

Seacroft

7 3 16 Rockport

Seaside House

Seaside House

4 2.5 10 Gloucester

The Spinnaker

The Spinnaker

3 2 6 Rockport

Squam Light

Squam Light

3 2 9 Gloucester

Straitsmouth Cove

Straitsmouth Cove

5 2 9 Rockport

Sunrise on the Cove

Sunrise on the Cove

4 2.5 12 Rockport

Sunset Cove

Sunset Cove

2 2.5 6 Gloucester

Terra Nova Cottage

Terra Nova Cottage

3 2 6 Gloucester

The View

The View

2 2 6 Rockport

Thurston Point Cottage

Thurston Point Cottage

3 1.5 7 Gloucester

Wingaerchic

Wingaerchic

3 2.5 6 Gloucester

Sea Glass on South

Sea Glass on South

3 3.5 6 Rockport

Twin Lights

Twin Lights

2 2 4 Rockport

Harbortown Hideaway

Harbortown Hideaway

3 2 8 Gloucester

Woodfall

Woodfall

2 1 4 Rockport

Dot's Place

Dot's Place

1 1 2 Rockport

Wiley's Way

Wiley's Way

2 2 4 Gloucester

Lofty Views

Lofty Views

2 1 5 Newbury

Sand Song at Good Harbor Beach

Sand Song at Good Harbor Beach

4 2 10 Gloucester

Plaisance

Plaisance

3 3 8 Gloucester

Ledge on Green

Ledge on Green

2 2 4 Rockport

Thorwald by the Sea

Thorwald by the Sea

2 1.5 4 Gloucester

Sur la Mer

Sur la Mer

5 2.5 10 Rockport

Mill Pond Cottage

Mill Pond Cottage

3 2 6 Gloucester

Sea For Miles

Sea For Miles

3 2 6 Gloucester

Sandpiper Cottage

Sandpiper Cottage

3 2 8 Gloucester

Sandy Bay Views

Sandy Bay Views

3 2.5 6 Rockport

Salt Marsh Cottage

Salt Marsh Cottage

4 3.5 12 Gloucester

Just For the Halibut

Just For the Halibut

3 1.5 6 Rockport

First Light

First Light

3 1 7 Rockport

Niles Beach House

Niles Beach House

4 2 8 Gloucester

Portside Glimpse

Portside Glimpse

1 1 2 Rockport

Portside Walkabout

Portside Walkabout

1 1 2 Rockport

Portside Overlook

Portside Overlook

2 2 5 Rockport

Portside at Front Beach

Portside at Front Beach

4 4 10 Rockport

Skyfall

Skyfall

7 4.5 16 Gloucester

Cape Hedge House

Cape Hedge House

3 3 6 Rockport

The Gallery

The Gallery

3 3 6 Gloucester

Painter's Perch

Painter's Perch

2 1.5 5 Gloucester

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