Updating...

Enter dates for more accurate prices

Cape Ann Rentals

Filter

Cape Ann Rentals

139 houses

Garden by the Sea: Relax & enjoy wonderful coastal views. Walk to the beach!

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$197

1 / 20

Beachside at Good Harbor

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 13

$426

1 / 17

Views on High: Enjoy ocean & village views from your private roof deck.

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 5

$223

1 / 19

Cozy Rockport Cottage with Ocean Views

Rockport cottage

2 bedrooms / 1 bathroom / Sleeps 5

$180

1 / 14

River Breezes: Direct riverfront with incredible sunsets

Gloucester cottage

3 bedrooms / 3 bathrooms / Sleeps 7

$397

1 / 19

Long Beach Place: Just steps from the white sand & surf.

Gloucester apartment

3 bedrooms / 2 bathrooms / Sleeps 8

$398

1 / 25

Quarry Crest House: Includes swimming rights to Little Parker quarry

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 10

$390

1 / 28

Wingaersheek beach private side 3 level treetop cottage house w/ 4 bedrooms

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 8

$298

1 / 23

The Sail Loft of Bearskin Neck

Rockport apartment

2 bedrooms / 1 bathroom / Sleeps 4

$155

1 / 15

Perrywinkle: Waterfront on Gloucester’s Rocky Neck.

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 7

$682

1 / 23

Two Beaches: Immaculate single-level 3BR between Long Beach & Good Harbor

Gloucester house

3 bedrooms / 1 bathroom / Sleeps 8

$260

1 / 27

At the Footbridge entrance to Good Harbor Beach

Gloucester house

6 bedrooms / 2 bathrooms / Sleeps 12

$567

1 / 18

Sunset Cove: Waterfront home in Goose Cove section of Gloucester

Gloucester house

2 bedrooms / 2 bathrooms / Sleeps 6

$547

1 / 20

Wonson Cove House: Rocky Neck, Eastern Point and Beaches

Gloucester house

4 bedrooms / 2 bathrooms / Sleeps 10

$427

1 / 31

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

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 12

$384

1 / 21

Beachmont: Easy access to Stagefort Park, Beaches & Downtown Gloucester

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 9

$419

1 / 40

18th Century Cottage with attached guest suite

Rockport cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$185

1 / 24

Remodeled 3BR Gloucester Annisquam River Cottage

Gloucester cottage

3 bedrooms / 1 bathroom / Sleeps 6

$199

1 / 24

Cozy Guest Studio

Gloucester studio

Studio / 1 bathroom / Sleeps 2

$164

1 / 11

Captain Quarters

Rockport b and b

1 bedroom / 1 bathroom / Sleeps 2

$159

1 / 14

Sea Vagabond: Amazing water views & close to Long Beach

Rockport house

3 bedrooms / 2 bathrooms / Sleeps 9

$257

1 / 21

Strawberry Cove House: Multi-level waterfront home

Gloucester house

4 bedrooms / 3 bathrooms / Sleeps 10

$913

1 / 34

The Little Red House with Prize Ocean View

Rockport house

2 bedrooms / 1 bathroom / Sleeps 4

$40

1 / 11

Bohemia RETREAT Studio

Gloucester apartment

1 bedroom / 1 bathroom / Sleeps 3

$115

1 / 26

Second Floor: 2+ Bedroom, 1.25 Bath

Manchester-by-the-Sea condo

3 bedrooms / 1 bathroom / Sleeps 5

$249

1 / 16

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

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 5

$110

1 / 46

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

Gloucester house

5 bedrooms / 2 bathrooms / Sleeps 10

$384

1 / 20

Waterfront 2 Bedroom !

Gloucester apartment

2 bedrooms / 1 bathroom / Sleeps 4

$149

1 / 14

Sage Hill: Easy access to both Gloucester & Rockport

Rockport house

4 bedrooms / 3 bathrooms / Sleeps 7

$296

1 / 23

Dragonfly

Gloucester house

5 bedrooms / 4 bathrooms / Sleeps 11

$497

1 / 7

Rockport Beach Escape: Stroll to Old Garden Beach or town.

Rockport house

5 bedrooms / 3 bathrooms / Sleeps 12

$850

1 / 22

Forever Views: You'll never want to leave your lounge chair!

Rockport house

4 bedrooms / 3 bathrooms / Sleeps 8

$953

1 / 28

The Robert House: 4 bedroom Rockport village house, sleeps 7

Rockport house

4 bedrooms / 1 bathroom / Sleeps 7

$378

1 / 25

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

Gloucester house

3 bedrooms / 2 bathrooms / Sleeps 6

$89

1 / 37

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

Gloucester cottage

7 bedrooms / 3 bathrooms / Sleeps 12

$1,060

1 / 28

Rockport Seaside Retreat: Walk to waterfront, town and beaches.

Rockport house

4 bedrooms / 2 bathrooms / Sleeps 7

$267

1 / 31

A Year-Round Vacation Home

Rockport house

3 bedrooms / 2 bathrooms / Sleeps 5

$249

1 / 15

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

Rockport cottage

1 bedroom / 1 bathroom / Sleeps 4

$241

1 / 16
Viewing 38 of 139
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more