$1,800
Total Monthly Price
143 Prospect St Unit 2, Gloucester, MA 01930
$1800 per month,1 bedroom- 1 BR Apartment, downtown 143 Prospect Street Gloucester MA. 1 year lease.Nice size 872 Sq ft 1 bedroom 2nd floor of two family house , on street parking,Walking distance to Train, Bus, Main St and Gloucester harbor.One block from Destino’s and Our Lady of Good Voyage Church.The apartment is ideal for a single or couple. The kitchen is equipped with a
$1,800
Total Monthly Price
143 Prospect St Unit 2, Gloucester, MA 01930
$1800 per month,1 bedroom- 1 BR Apartment, downtown 143 Prospect Street Gloucester MA. 1 year lease.Nice size 872 Sq ft 1 bedroom 2nd floor of two family house , on street parking,Walking distance to Train, Bus, Main St and Gloucester harbor.One block from Destino’s and Our Lady of Good Voyage Church.The apartment is ideal for a single or couple. The kitchen is equipped with a
$4,750
Total Monthly Price
48 Rowley Shore, Gloucester, MA 01930
Winter Rental | November 2 – April 1Oceanfront Winter Retreat in Lanesville, GloucesterEscape to the peaceful seaside village of Lanesville and enjoy a comfortable winter stay in this beautifully remodeled oceanfront home. With stunning views of Ipswich Bay, spacious living areas, four bedrooms, two remodeled bathrooms, and a fully equipped kitchen, this home is ideal for a winter
$2,800
Total Monthly Price
4 Lobster Ln, Gloucester, MA 01930
Furnished 6 rooms, 3 bedrooms, 1 bath cottage on Magnolia Beach, $2,800 a month, plus utilities. Walk Magnolia beach and Shore Road from your front door. Beautiful sunsets overlooking Coolidge point and Boston Skyline. Ocean and harbor views from the living room, dining room, kitchen, large side deck and screened porch. Great location. Washer and dryer, outdoor shower, plenty of parking. First,
$2,900
Total Monthly Price
540 Washington St, Gloucester, MA 01930
On the River with views. 2 bedroom, 2 bath single family. Utilities included, except Oil. Waterfront. 2 Private Decks. Driveway. Large Kitchen, Dining Room, Living Room. Breathtaking Sunsets. Grills. Fire Pit. Washer Dryer In unit. No past evictions. Includes electricity, hot water, cable, and WiFi. Spacious. Year Round Property
$7,500 Per Month
1 Sandy Way, Gloucester, MA 01930
One Week Rentals Available: Experience coastal living in this furnished weekly rental with deeded access to Coffins Beach. The open kitchen, dining, and living area flows to a bright family room with a cathedral ceiling and deck. A 3rd-floor bonus room opens to a roof deck with panoramic ocean views. Accommodations: King ensuite, 2 Queen rooms (shared bath), trundle room, sunroom with daybed, and
Kimberly Tipert Noyes Engel & Volkers By the Sea
$3,850
Total Monthly Price
660 Washington St, Gloucester, MA 01930
Winter Rental Available: November 3, 2026-May 15, 2027Waterfront on the Annisquam River in Gloucester, this exceptional winter rental boasts wonderful views of the river and of Ipswich Bay. You will never forget the sunsets seen from the deck or from the delightful gazebo.This home has a custom kitchen, spacious open concept living/dining room and lots of windows. There are
$5,000 Per Month
17 Fort Hill Ave, Gloucester, MA 01930
SEASONAL and FlEXIBLE TERM RENTAL - Charming English Tudor Carriage House privately located in the heart of Eastern Point within walking distance of two sandy beaches, DogBar Breakwater, Eastern Point Light House and many nature paths; only a 10 minute drive to Rt. 128 and all things Gloucester. Just minutes from Rocky Neck Art Colony and Gloucester Stage Company. Bicycle to town or around Cape
Lois Budrose Lois Budrose Realty
$2,300
Total Monthly Price
10 Josephs Way, Gloucester, MA 01930
Winter Rental Available: October 1, 2026 - May 15, 2027Just a half mile from Gloucester's Good Harbor Beach, Joseph's Way is a delightful two-bedroom rental nestled on a quiet hidden side street with just four other houses.Freshly renovated and decorated, enjoy the ease of one-level living with a spacious open plan dining/living room which expands to the fully-applianced kitchen
$3,100 Per Month
16 Warwick Rd Unit WINTER, Gloucester, MA 01930
WINTER RENTAL: Ideally situated between two of Cape Ann's most beautiful beaches; Long Beach and Good Harbor, this impeccable one level home features an open-plan kitchen/dining area with granite countertops, stainless steel appliances, and gas range. It's comfortable living room features large windows and a flat screen tv over the decorative fireplace. There are 3 bedrooms: the primary has a
Carole Sharoff AVH Realty
$3,150
Total Monthly Price
31 Chester Square, Gloucester, MA 01930
Winter Rental: Available October 1, 2026-May 31, 2027 (Utilities Included)Located in the heart of the quaint and charming village of Annisquam, this newly renovated Gloucester cottage offers the perfect off-season home. The bright and airy ground floor has many windows, letting in lots of natural light. The full bathroom on the main level has a shower over tub. A three-season sunroom runs
$4,400 Per Month
1 Sandy Way, Gloucester, MA 01930
Winter Rental: 10/1/2026-5/28/2026. This serene retreat is perfect for sunsets and seaside relaxation. Available weeks:August 8-15 $9,000. August 22-29. $9,000. September 14-20 $7,500. September 21-27 $7,500 Discover the best of coastal living with this beautifully furnished and equipped weekly rental, deeded access to Coffins Beach. Whether you enjoy peaceful walks along the shoreline, stunning
Kimberly Tipert Noyes Engel & Volkers By the Sea
$3,975
Total Monthly Price
206 Atlantic St, Gloucester, MA 01930
Winter Rental Available: October 1, 2026- May 31, 2027This private contemporary furnished house is perched on a hilltop near Wingaersheek Beach. Inside is an open plan living/dining room with vaulted ceilings, hardwood floors, and large oversized windows which fills the room of natural light. The dining area includes a large table with plenty of seating. The eat-in kitchen with breakfast
$12,000 Per Month
15 Wyoma Rd, Gloucester, MA 01930
SHORT OR LONG TERM RENTAL. WEEKLY SUMMER RATES VARY....Rare opportunity to rent this spectacular custom-built home in the Private section of Wingaersheek Beach. Stunning ocean views from every room of this 4-bedroom home. Large bedrooms, custom bathrooms, beautiful chef's kitchen leads to a 2-story family room w/ fireplace and direct access to an oversized deck with stunning ocean views.
Gianni De Palma GDP Real Estate Group, LLC
$3,950
Total Monthly Price
64 Riverview Rd, Gloucester, MA 01930
Winter Rental Available: December 1, 2026-May 31, 2027Welcome to Tidebend, a beautifully crafted 6-bedroom, 2.5-bath home offering serene views of the Annisquam River. This thoughtfully designed home blends quality craftsmanship with comfort and practicality, featuring custom woodwork and built-ins throughout that enhance both character and functionality. The home’s inviting
$2,900 Per Month
11 Bond St, Gloucester, MA 01930
FURNISHED WINTER RENTAL unit 1 9/1/26-5/31/27!!!Live the coastal lifestyle in this delightful 2 bedroom one bath single family home just moments from Stage Fort Park and Pavillion Beach. Enjoy your own private driveway, a fantastic fenced yard , a cozy deck off the kitchen, perfect for morning coffee or evening unwinding. The enclosed front porch offers bonus space for storage. Clean bright white
Karin Gitto Bancroft Realty Group
$2,975
Total Monthly Price
11 S Kilby St, Gloucester, MA 01930
Winter Rental Available: November 3, 2026 - May 15, 2027 (Dogs Welcome!)Situated on a knoll in Gloucester's Bay View neighborhood, Helena House offers seasonal views of Ipswich Bay from the balcony of the second-floor bedroom. Decorated with a European sensibility, this home is bright and comfortable with hardwood floors throughout.A Queen Anne-style house, you can access the
$5,250 Per Month
44 Ye Olde County Rd, Gloucester, MA 01930
WINTER RENTAL: This serene waterfront home offers breathtaking views from nearly every room. Enjoy the private dock for boating, swimming, and kayaking, surrounded by cedar trees for privacy and a nature-filled experience. Relax on the screened-in porch or stroll the sandbank at low tide. Located on picturesque Rust Island, just a short drive from Gloucester and Rockport, the property includes a
Julia Virden J. Barrett & Company
$4,250 Per Month
2 Glenmere Rd, Rockport, MA 01966
Short term monthly rental opportunity from October 1 - May 31st! Owners will consider any length of time within those dates. Newly renovated cottage just 600 feet from Long Beach in Rockport. Conveniently located within a 5 minute drive to both downtown Gloucester and Rockport. This charming getaway features 4 bedrooms consisting of 1 king, 2 queens, and 2 twins, providing a blend of comfort and
Louise Touchette Coldwell Banker Realty - Lynnfield
$3,900 Per Month
4 Diamond Ave, Gloucester, MA 01930
Charming Annisquam Village Home. This seasonal rental starts 9/1 through 6/1Discover this cozy retreat nestled in the heart of Gloucester's coveted Annisquam Village, just a short drive from Boston.Enjoy easy access to Diamond Cove, a stunning rocky beach, located just across the lane.This delightful home offers a perfect blend of comfort and coastal charm. The open-concept living and dining area
Brian Rothe Coldwell Banker Realty - Manchester
$3,000 Per Month
1101 Washington St Unit WINTER, Gloucester, MA 01930
WINTER RENTAL AVAILABLE NOVEMBER 1 TO MID-MAY. Enjoy views of Lane's Cove as well as proximity to the village shops and Plum Cove Beach from this cozy perch in Lanesville. Some might say that Gloucester is even more beautiful in the cooler months. This single family home has been well maintained and thoughtfully renovated in recent years with improvements made to the kitchen, baths and other
Amanda Armstrong Compass
$35,000 Per Month
62 Crafts Rd, Gloucester, MA 01930
Modern Cape Ann coastal retreat. Sitting on 1.4 waterfront acres with granite outcroppings, mature trees, and gardens. Private deep-water dock, 5 feet at low tide, accommodates 2-3 boats. Riverfront peninsula with sweeping water and marsh views, perfectly located in the middle of the Annisquam River. Take trips out to Ipswich Bay, the bustling Gloucester Harbor and open waters beyond. Features
John Farrell Coldwell Banker Realty - Beverly
$24,000 Per Month
14 Sunset Point Rd Unit SUMMER, Gloucester, MA 01930
WEEKLY SUMMER RENTAL AVAILABLE WITH AVAILABILITY IN SEPTEMBER for $6000 per week with a two week minimum. Idyllic oceanfront retreat in Lanesville in stunning and private setting in one of the North Shore’s most scenic communities. This is the perfect base for exploring the many delights of Lanesville, from its rugged shoreline to the colorful village with its shops and cafe. Head to beautiful
Amanda Armstrong Compass
$4,200 Per Month
40A Thurston Point Rd, Gloucester, MA 01930
Built in 2023, this exceptional freestanding ADU home blends modern design with luxurious comfort. Featuring high-end wood floors throughout, it boasts radiant heat and air conditioning, ensuring year-round comfort. The spacious open-plan layout is highlighted by vaulted ceilings, enhancing the sense of light and space.The chef's kitchen is a standout, equipped with top-of-the-line stainless
Lynda Hemeon Coldwell Banker Realty - Manchester
$2,000 Per Month
3 Point Rd, Gloucester, MA 01930
Rare opportunity to enjoy coastal living at an incredible price! Available as an 8-month furnished rental from October 1st through May 31st, this charming single-family beach ranch is located just steps from beautiful Wingaersheek Beach.This spacious home features an open-concept living and dining area, 4 bedrooms, 2 full bathrooms, central air conditioning, an in-unit washer and dryer, and two
Gina Arzola Madelyn Garcia Real Estate
$6,000 Per Month
25 Magnolia Ave, Manchester, MA 01944
Cape Ann coastal living at its best! Near picturesque beaches, scenic trails, and all that Manchester by the Sea has to offer, this rare find features spacious rooms, flexible living areas, and exceptional indoor/outdoor spaces designed for entertaining, relaxing, and hosting. Set on a beautiful private lot with gardens, stone walls, flowering trees, yard space, and oversized shed. Three-bedroom
Krista Julian Coldwell Banker Realty - Manchester
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