$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
$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
$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
$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
$2,495
Total Monthly Price
45 Western Ave Unit 2, Gloucester, MA 01930
Prime waterfront Year-Round Two-Bedroom plus office Rental at the historic Stacey Boulevard and renowned Gloucester Fisherman's Statue! Enjoy the southern exposure of this five-room, two-bedroom apartment as you overlook Gloucester's Historic Harbor from your living room window/private deck while the sun and moon glisten on its waters. This second-floor unit with single-level living offers
Starting at $2,050 Plus Fees
950 Heights at Cape Ann, Gloucester, MA 01930
Quietly nestled at the highest point in Gloucester is the Heights at Cape Ann, an exceptional apartment home community. Stop by our onsite management office to view our one, two, and three bedroom floor plans. The Heights at Cape Ann is a pet-friendly apartment community that offers a modern fitness center, swimming pool, fire pit, resident's lounge, Wi-Fi cafe, and units with terraces boasting
The Heights At Cape Ann
$2,150 Plus Fees
67 Friend St Unit 2, Gloucester, MA 01930
Property Id: 681560 Welcome to your new home at 67 Friend St in Gloucester, MA! This charming 1 bedroom, 1 bathroom condo is perfect for a single person or couple. Located at garden level for ease of entry and exit! With amenities such as a dishwasher, garbage disposal, and on-site laundry, you'll love living here. Enjoy off-street parking and being close to parks and downtown. Rent is
$1,500
Total Monthly Price
7 Ellery St Unit 2, Gloucester, MA 01930
- Available October 1st.- Well-kept 1 Bedroom, 1 Bath Apartment.- Open kitchen and living room, separate bedroom, and tile floors throughout.- Includes smooth top stove, fridge, washer/dryer, walk in tiled shower, and hot water.- Electricity paid by tenant.- On street parking with off street parking during snow storms.- Easy 1/2-mile commute to Route 128.- No smoking
$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,
$2,775
Total Monthly Price
19 Atlantic Rd, Gloucester, MA 01930
Winter Rental Available: October 1, 2026-May 31, 2027Welcome to this modern two-story condo located in the desirable Bass Rocks neighborhood. This home boasts beautiful views of the Bass Rocks Golf Course while being just .2 miles from the Good Harbor Beach Footbridge. This 2-bedroom, 1.5-bath home combines contemporary style with comfortable living.The open floor plan is filled
$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
$4,000
Total Monthly Price
37 Rocky Neck Ave Unit Winter Rental: The Gallery, Gloucester, MA 01930
Winter Rental Available: October 1,2026-May 31, 2027One-of-a-kind waterfront multi-level property on Rocky Neck, America's oldest art colony. Enjoy views of Smith Cove and the Gloucester skyline.The main living area is on the second floor where there is a spacious living room overlooking the cove. Also on this level is a fully equipped kitchen with granite countertops and
$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
$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
$2,800
Total Monthly Price
5 Revere St Unit One, Gloucester, MA 01930
First floor pristine fully outfitted for summer rental-all new in owner occupied home on edge of Annisquam. Comes with Lighthouse Beach pass. NO smoking / NO petsCleaning dep $200. Sec Dep $500.$2800/mo ALL Utilities Sept 1- June 1, 2027Sleeps 4 (second full bed futon in LR)Full use of yard (picnic table, Adirondack chairs, hammock)
$2,000
Total Monthly Price
42 Fort Square Unit 1R, Gloucester, MA 01930
First floor 2 Bed, 1 Bath apt in a four family home located at Stage Fort Park along Gloucester's harbor on a one way street. Beautiful water views from the front bedroom. Beach and Stage Fort Park at end of street. The apartment is in ready to move in condition freshly painted. Accessed through its own private entrance, this one level unit offers plenty of sunlight. The layout includes an eat in
$3,000
Total Monthly Price
5 Pirates Ln, Gloucester, MA 01930
WINTER RENTAL - Available: September 1, 2026-June 15, 2027 (Utilities Included)Tucked away along the harbor, this charming East Gloucester end-unit condo is part of a classic coastal Victorian-era complex overlooking picturesque Smith Cove and Gloucester Harbor. With its private entrance and two spacious decks, this light-filled retreat is the perfect seaside escape.Step inside
$2,400 Per Month
2 Spring St Unit A, Gloucester, MA 01930
Enjoy comfortable first-floor living in this charming, fully furnished one-bedroom, two-full-bath apartment. The unit also features an additional room with closet space, offering flexible space for storage, an office, or other uses. Relax and enjoy the outdoor patio, with convenient access to nearby shops, restaurants, and multiple Gloucester-area beaches. The property also offers easy highway
Alyssa Anderson Coldwell Banker Realty - Beverly
$1,800
Total Monthly Price
11 Stanwood Ave Unit 1 bedroom 3rd floor apartment, Gloucester, MA 01930
3rd floor 1 bedroom apartment, quiet building in peaceful residential neighborhood around the corner for public landing on Little River. Good sized shared yard space, private deck, coin op laundry in basement. Pets considered on case-by-case basis.
$2,495 Per Month
41 Western Ave Unit 2, Gloucester, MA 01930
Conveniently located 2 bedroom/2 full bath apartment with unobstructed views of Gloucester Harbor! Impeccably maintained rental with hardwood floors throughout and a spacious granite kitchen. Laundry in unit for your convenience. Good closet space. Detached garage available for one car and also 1 driveway spot. Enjoy the quiet beauty of Cape Ann from the third Floor front bedroom windows
Robin Capone Irving Realty
$2,150 Per Month
18R Waterman Road Winter Unit 1, Gloucester, MA 01930
Welcome to your Winter Hideaway on Waterman Road! All Utilities are Included in this well maintained sun-filled furnished rental. Spend hours exploring the private side of Wingaersheek with stunning sand dunes, sand bars, sea kites & the occasional whiskered seal. This sun filled unit has a well equipped kitchen, a large open concept dining area with easy streamline access from living room to
Mary Matthews Coldwell Banker Realty - Manchester
$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
$1,700 Per Month
45 Main St Unit 3, Gloucester, MA 01930
Spacious 725 SF 3rd floor waterview studio apartment overlooking Gloucester's inner Harbor Cove and outer harbor! Modern fully applianced kitchen and bath! Outside deck to sit out and enjoy the view in Summer. Wall to wall carpet in living area. 3 large skylights, ample closet space, lots of exposed brick walls and knotty pine walls/ceiling. Here is your chance to live in the West End,
Peter Lane North Shore's Gold Coast Realty
$3,200
Total Monthly Price
21 Addison St Unit 21 Addison street unit. 2, Gloucester, MA 01930
Freshly painted and packed with space! This 3-bedroom, 1-bath apartment offers classic hardwood floors, a huge living room, a separate dining room, and a dedicated home office. The Space: Generous room sizes, fresh neutral paint, and abundant natural light. The Extras: Private office space for remote work/studying, formal dining area, and beautiful hardwoods throughout. The Location:
$2,300 Per Month
124 Mount Pleasant Ave Unit 1, Gloucester, MA 01930
Beautifully furnished winter rental available September 15, 2026–May 30, 2027. This bright, two-level East Gloucester townhouse lives like a single-family home and is tucked away on a quiet dead-end street near Niles and Good Harbor Beaches, Rocky Neck, and Bass Rocks Golf Club. The open-concept main level features a granite and cherry kitchen with an oversized island, spacious living room with
Patricia McCormick J. Barrett & Company
$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
$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
$3,150
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
$1,800 Per Month
31 Western Ave Unit 19, Gloucester, MA 01930
Updated one-bedroom on the Boulevard featuring an open-concept kitchenette and living room, full bath, and vinyl plank flooring. Heat and hot water are included, with common laundry and parking for one car. Conveniently located near the Commuter Rail station, downtown Gloucester shops and restaurants, Stage Fort Park, Half Moon Beach, and Pavilion Beach directly across the street.
Emma Fula Charlesgate Realty Group, llc
$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
$2,100 Per Month
8 Flume Rd Unit 4, Gloucester, MA 01930
Charming renovated 1st floor, 1-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
$2,750 Per Month
16 Magnolia Ave Unit 7, Gloucester, MA 01930
Charming renovated 2-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
$2,100 Per Month
16 Magnolia Ave Unit 12, Gloucester, MA 01930
Charming renovated 1-bedroom apartment available now! This well-maintained unit features modern updates throughout, a bright and inviting living space, and the convenience of off-street parking. Heat and hot water is included in the rent. Conveniently located near Gloucester’s shops, restaurants, beaches, and commuter routes.
Desiree Taylor Desired Homes Realty LLC
$2,100 Per Month
9 Friend St Unit 1, Gloucester, MA 01930
This year-round, sunlit four-room apartment rental includes heat and hot water. Meticulously maintained first-floor unit has an open concept eat-in kitchen, living room, and outside deck with views of our working harbor. A heated front porch, a slider to a large 19' x 8' deck at the back that overlooks the working harbor, polished hardwood floors, period coffered ceilings, a washer and dryer, a
Ana Silveira J. Barrett & Company
$3,500 Per Month
11 Leonard St Unit 2, Gloucester, MA 01930
SEASONAL WINTER RENTAL WITH WATER VIEWS! Spend the off-season in one of Annisquam's most picturesque settings, perched in the heart of the village with sweeping views of the Annisquam River and the pristine shores of Wingaersheek Beach beyond. This beautifully preserved period home blends timeless New England charm with modern comforts, featuring exposed beams, hardwood floors, multiple
Paula Polo-Filias J. Barrett & Company
$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
$2,900 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
$1,750 Per Month
11 Fair St Unit 3, Gloucester, MA 01930
Gloucester-Third floor 2 bedroom, tenant pays heat hot water and electricity. On site coin-op laundry and off street parking. Landlord will consider a cat or small dog.
Robin McKeon McKeon / Corcoran Real Estate
$1,750 Per Month
50 Taylor St Unit U1R, Gloucester, MA 01930
Downtown one bedroom Tenants pays heat hot water and internet. On street parking. Cats allowed. No laundry facilities.
Robin McKeon McKeon / Corcoran Real Estate
$3,500 Per Month
55 Mansfield St Unit B, Gloucester, MA 01930
Experience year-round waterfront living in this beautifully renovated 3-bedroom, 2-bath residence overlooking Gloucester Harbor. Thoughtfully updated with high-end finishes, this home features an open floor plan, a designer kitchen with quartz countertops, stainless steel appliances, a large center island, and abundant cabinetry. The spacious living and dining areas showcase panoramic ocean
Levana Group RE/MAX Beacon
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