Houses for Rent in Annisquam, MA

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ABOUT THIS HOME
House for Rent in Annisquam:
Winter Rental: Available October 1, 2025-April 30, 2026 (Utilities Included) Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the pe

$3,150/mo

Fees may apply

3 beds2 baths1,596 sq ft

31 Chester Sq, Gloucester, MA 01930

Available 10/01 • Pets welcome • Laundry in unit

ABOUT THIS HOME
House for Rent in Annisquam:
The rental period is September 6, 2025 through May 22, 2026 and the rate is $5,900 per month, which includes all utilities except for cable/telephone/tv. Perfect for sabbaticals, retirees and home ren

$5,900/mo

Fees may apply

4 beds2 baths2,500 sq ft

878 Washington St, Gloucester, MA 01930

Laundry in unit • Parking • A/C

ABOUT THIS HOME
House for Rent in Annisquam:
Situated on a knoll in Gloucester's Bay View neighborhood, this furnished winter rental is on a rise above Ipswich Bay offering peekaboo views from the second floor bedroom. Newly renovated, this home

$2,950/mo

Fees may apply

3 beds1.5 baths1,291 sq ft

13 S Kilby St Unit WINTER, Gloucester, MA 01930

Available 09/15 • Parking • Patio/Balcony

ABOUT THIS HOME
House for Rent in Annisquam:
WINTER: Beautifully renovated home located directly on Lobster Cove in the historic village of Annisquam. Around 1623, Captain John Smith described the cove as a "a safe harbor in a Northeast storm."

$3,975/mo

Fees may apply

4 beds3 baths2,004 sq ft

1 Chester Sq Unit WINTER, Gloucester, MA 01930

Available 09/15 • Parking • Patio/Balcony

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ABOUT THIS HOME
House for Rent in Annisquam:
Welcome to Folly Cove! This charming single-family home is now available as a year-round rental! Just steps from the Ocean and Halibut Point State Park. Featuring over 1,100 sq. ft. of comfortable l

$3,200/mo

Fees may apply

1 bed1.5 baths1,104 sq ft

334 Granite St, Rockport, MA 01966

Pets welcome • Parking • Car-dependent

ABOUT THIS HOME
House for Rent in Annisquam:
Welcome to your dream waterfront retreat! This brand-new construction offers unparalleled luxury and convenience, boasting 4 bedrooms, 3 bathrooms, and a deep water dock. Located in the prestigious Wh

$12,500/mo

Fees may apply

4 beds3 baths3,200 sq ft

8 Riverside Rd, Gloucester, MA 01930

Available 10/01 • Parking • A/C

ABOUT THIS HOME
House for Rent in Annisquam:
Winter Rental Available: January 3-April 30, 2026 (Available until August at a higher rate, inquire for details) Mill Pond Cottage offers a unique blend of old-world charm and modern comfort. With thr

$2,975/mo

Fees may apply

3 beds2 baths1,371 sq ft

379 Washington St, Gloucester, MA 01930

Available 01/03 • Laundry in unit • Parking

ABOUT THIS HOME
House for Rent in Annisquam:
Winter Rental available from 10/1/2025- 6/30/2025. 4 Bed 2 full bath, 1 car garage. Heat by oil. Tenant responsible for oil heat and electricity. No smoking no pets. Incredible sunrises over Wingaersh

$2,995/mo

Fees may apply

4 beds2 baths1,500 sq ft

3 Point Rd, Gloucester, MA 01930

Available 10/01 • Parking • Car-dependent

ABOUT THIS HOME
House for Rent in Annisquam:
WINTER RENTAL: Available November 1-May 31, 2026 Experience river life at its best along the banks of Mill River when you stay at this spectacular waterfront rental home with exquisite water views, a

$3,350/mo

Fees may apply

3 beds2 baths1,885 sq ft

420 Washington St, Gloucester, MA 01930

Available 11/01 • Dogs welcome • Laundry in unit

ABOUT THIS HOME
House for Rent in Annisquam:
OCEANFRONT IN LANESVILLE SUMMER RENTAL WITH DATES STILL AVAILABLE STARTING IN MID-AUGUST. Idyllic summer retreat in stunning and private oceanfront setting in one of the North Shore's most scenic comm

$20,000/mo

Fees may apply

3 beds2.5 baths1,518 sq ft

14 Sunset Point Rd, Gloucester, MA 01930

Parking • A/C • Car-dependent

Property at 1 Sandy Way, Gloucester, MA, 01930, 4 beds, 3 baths, [object Object]

$6,800/mo

4 beds3 baths2,164 sq ft

1 Sandy Way, Gloucester, MA 01930

Property at 1101 Washington St, Gloucester, MA, 01930, 3 beds, 3 baths, [object Object]

$2,900/mo

3 beds3 baths1,822 sq ft

1101 Washington St, Gloucester, MA 01930

Property at 10 Josephs Way, Gloucester, MA, 01930, 2 beds, 1 bath, [object Object]

$2,550/mo

2 beds1 bath688 sq ft

10 Josephs Way, Gloucester, MA 01930

Property at 44 Ye Olde County Rd, Gloucester, MA, 01930, 4 beds, 2 baths, [object Object]

$5,250/mo

4 beds2 baths1,708 sq ft

44 Ye Olde County Rd, Gloucester, MA 01930

Property at 62 Crafts Rd, Gloucester, MA, 01930, 4 beds, 2 baths, [object Object]

$12,500/mo

4 beds2 baths3,300 sq ft

62 Crafts Rd, Gloucester, MA 01930

Property at 15 Wyoma Rd, Gloucester, MA, 01930, 4 beds, 3.5 baths, [object Object]

$15,000/mo

4 beds3.5 baths3,584 sq ft

15 Wyoma Rd, Gloucester, MA 01930

Property at 2 Bungalow Rd Unit Winter, Gloucester, MA, 01930, 4 beds, 2 baths, [object Object]

$3,500/mo

4 beds2 baths1,458 sq ft

2 Bungalow Rd Unit Winter, Gloucester, MA 01930

Property at 41B Wingaersheek Rd Unit 1, Gloucester, MA, 01930, 2 beds, 2 baths, [object Object]

$3,900/mo

2 beds2 baths1,150 sq ft

41B Wingaersheek Rd Unit 1, Gloucester, MA 01930

Property at 1 B Pigeon Hill Ct, Rockport, MA, 01966, 2 beds, 1.5 baths, [object Object]

$2,975/mo

2 beds1.5 baths1,288 sq ft

1 B Pigeon Hill Ct, Rockport, MA 01966

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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