Waterfront holiday rentals in Winthrop

Lakefront Suite Two-Room, Comfy, Tranquil

Located on a lovely small lake with a panoramic view from the bedroom, private spa-like bathroom, cotton linens, a comfy bed, A/C and a living room-so not an 'entire' home but more than just a room! Quietly watch lake nature or boats going by, or choose to swim, kayak, or fish. Enjoy industrial history at Lowell's National Park mills, take a forest walk nearby, or drive 10 min. to Nashua for its many restaurants and tax-free shopping. 1 hr from Boston and near many New England highlights.

Oceanfront Pool. Close to Boston. Free Parking.

Enjoy a relaxing & tranquil beach setting while having quick access to Boston and all it has to offer. Stunning ocean views can be seen from our seasonal saltwater pool and all-season hot tub (exclusive during your stay). We are 4 short miles from Boston & public transportation is easily accessible. Winthrop is a welcome relief from the hustle and bustle of the city, where you can come "home" and wind down to the sound of ocean waves, seaside birds, gorgeous sunrises, and beautiful moon rises.

Lakeside apartment, patio, hot tub, outside shower

Private apartment, has lock box access, includes bedroom, living room, kitchen & bathroom. Private from public, patio and hot tub overlooks lake and conservation land. No stairs. Sofa converts to a comfortable queen or twin beds Kitchen is stocked with dishes, pots and pans for 4, coffee and water Hot tub always 104 degrees Kayak, sail boats & swimming available. Portable fire pit. $25 pet fee, 1 pet only under 50 #'s. Tesla EV charging Covid 19 CDC cleaning and disinfecting procedures.

Truly Ocean-Front!: Spacious Family Home + Pets

Truly ocean-front! Don’t be fooled by Winthrop listings of side-street homes. This is an entire 1st floor unit with a private entrance. In an owner-hosted, classic triple-decker home with normal family/town sounds. Pro-cleaned and pet-friendly. Adjacent to Boston by car, ferry/transit. Family time with everything you need. Enjoy our rocky beach or walk a few blocks north to the sandy, lifeguarded stretch. Cafés and restaurants are walkable, and groceries deliver. Quiet hrs: 10pm-7am for all.

Beachmont Guest Suite

Experience tranquility in our modern guest suite with stunning ocean views and a private deck overlooking the Atlantic. Wake up to breathtaking sunrises and relax by the cozy gas fireplace. Features a fully equipped kitchen with island seating, a comfortable queen bed, a plush sectional couch, and a luxurious bathroom. Just minutes from Boston, enjoy beachfront living—ideal for romantic getaways, peaceful retreats, or business travelers. Book now to experience the best of beachfront living!

Amazing Ocean View In-Law Apt.

Step into a breath-taking magical seaside residence with 180-degree ocean views. This private in-law apartment has a sprawling lawn, steps to the ocean, and landscaped gardens. The apartment has one queen size bed with sliding doors opening out to the lawn, a queen pullout couch, granite counter-top complete kitchen including micro and dishwasher, ping-pong table, flat screen TV, home office and bathroom/ shower. The apartment has been thoroughly cleaned and meets all covid-19 standards.

Rock Steady - Panoramic Ocean Front Home

Just north of Boston, our home is a mid century ranch we renovated in 2019. The Airbnb is a spacious ground floor living space surrounded by a private cove that is truly breathtaking. 1000 square feet of sunlit comfort. Enjoy the sound of the waves, stunning sunrises and a landscaped back patio that abuts our cliff. In the summer take advantage of the town beach down the street. During the winter relax in front the fireplace. Top it all off with hi-speed Wi-fi – it's a perfect getaway.

Get to The Point, Winthrop

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy one bedroom, private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

House of Three Gables

Nestled within the historical Derby Street neighborhood in Salem, MA, The House of Three Gables offers 3 comfortable bedrooms, a livingroom w/tv, and a full kitchen. Free Wi-fi and parking available on premise. This prime location is less than a 3 minute stroll to the Salem/Boston Ferry with museums, restaurants, and shops around every corner. We welcome everyone into our quaint home, baby accomodations are available but, please no pets. We look forward to your visit!