Houses for Rent in Gloucester, MA

Set in Gloucester, MA, this 3-bed, 1.5-bath house sits between Long Beach and Good Harbor Beach for a September-April winter rental. The 1,402 sqft single-level layout features an open kitchen with granite counters and stainless appliances, plus a three-season sunroom and outdoor shower. Water and sewer included with utilities up to $425/month, parking for 4 cars, and a deck overlooking the spacious yard.

Experience stunning river views in this spacious 6-bedroom, 2.5-bath home. Featuring custom woodwork and cozy spaces, the inviting layout includes a sunny kitchen and a spacious living room. Enjoy mornings on the farmhouse-style porch and evenings watching breathtaking sunsets. Off-street parking for up to 6 cars and dog-friendly policies make this a perfect winter rental. Utilities included up to $350/month with no smoking allowed.

Experience tranquil coastal living in this charming 2-bedroom, 1.5-bathroom getaway. Highlighted by breathtaking views of Smith Cove, this home features outdoor spaces for soaking up the sun, including a cozy deck and balcony. The bright, open living area with exposed beams and a fireplace exudes warmth, while the eat-in kitchen offers a delightful breakfast nook. Conveniently located near galleries, shops, and beaches, this winter rental is a perfect haven for art lovers and outdoor enthusiasts alike.

This newly renovated 3-bedroom cottage exudes charm in the quaint village of Annisquam. Bright and airy interiors feature a spacious main level with a formal dining area and a sunroom. The primary bedroom is equipped with a queen bed, complemented by generous closet space throughout. Enjoy the private backyard with garden seating. Perfect for winter stays, utilities are included, making this a comfortable, relaxing retreat by the water's edge. Pets welcome!

Experience coastal living in this spacious 4-bedroom, 2-bath contemporary home on a private estate. With 2,500 sq. ft. of bright living space, enjoy panoramic Ipswich Bay views, a large deck, and access to private sandy beaches. The open living area features high ceilings and a brick fireplace, while the kitchen boasts granite counters and a breakfast bar. Complete with on-site amenities like tennis courts, kayaks, and a play area, it's perfect for relaxation and outdoor fun year-round.

Enjoy winter living in this delightful Queen Anne home featuring three bedrooms and 2.5 baths. With 1,717 sq ft of bright, comfortable space, it boasts a primary bedroom with a private balcony and scenic Ipswich Bay views. Relax in the lush backyard with a slate patio and outdoor shower. The location offers a short stroll to Hodgkin's Cove and Plum Cove beach, making it ideal for dog lovers and outdoor enthusiasts seeking tranquility and charm.

This freshly renovated 2-bedroom winter rental offers convenient one-level living just half a mile from Good Harbor Beach. Enjoy an open-plan dining/living space, a fully-equipped kitchen with breakfast bar, and a second sitting area leading to a spacious deck overlooking a peaceful wooded lot. Amenities include in-unit laundry, parking for 2+, and dog-friendly options with approval. Utilities included up to $250/month for a hassle-free experience.

This stylish winter rental features a bright open-plan living/dining area with vaulted ceilings and sweeping windows, creating a warm and inviting atmosphere. Perfect for up to 6 guests, the home includes three bedrooms, 2.5 baths, and a spacious deck that invites outdoor relaxation. Enjoy amenities like a game room, private beach access, and garage parking. Dogs are welcome, and utilities like internet and heat are included, making this the ideal seasonal getaway!