Beachfront vacation rentals in Winthrop

Beach Home next to Boston & T, King Bed, Park Free

Enjoy a comfortable stay in this beautiful, newly renovated 3 bed 2 bath apartment only 150 yards to the beach and convenient access to Boston by car (15-25min) or public transport (30-45min). It's a spacious 1300 sqft, was just fully remodeled, retains plenty of character and boasts loads of windows and light. Recharge from your trip in style with a fully equipped kitchen, three new comfortable beds, 55" TV, sofa, work & dining area, new bathrooms, walk-in closet, and free off-street parking.

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.

Quiet Neighborhood Luxury Stay

The apartment is brand new with a modern feel to it. Available with all the amenities needed for your convenience. Very quiet, clean, and safe neighborhood. Close to everything you desire, 1 minute to the beach, 8 minutes away from the train station, 1 minute away from the T-Bus stop, 9 minutes to Logan Airport, 12 minutes to Downtown Boston, 15 minutes away from Encore Casino, food and coffee shops, such as Starbucks and Dunkin' Donuts in the area. Perfect for a family stay or a business trip.

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.

Harbor View Walk to Beach & Town, 6Guests KingBeds

Spectacular Gloucester home on Cape Ann. Walk to Stage Fort Park & local beaches right across the street. Gloucester center is about 1 mile. On the way to town, walk by beaches & the park with waterfront tennis & bocce ball courts, plus a great water view playground and playing fields. Just beyond the park is famous Stacy Boulevard with the Fisherman's Memorial Monument along the waterfront. There are beautiful white sandy beaches (Good Harbor, Wingaersheek, Singing, & Crane's Beach).

Seadrift Inn - 2 bedroom 2nd floor apt by the sea!

We are at Salem Willows - family-friendly activities, the ferry, trolley, train, downtown, and nightlife are all close by. Seadrift is perfect for couples traveling together as it has two bedrooms, both with King beds, a large living room, and bathroom. You have a private entrance and it is located on the second floor. You can walk to four beaches within minutes, one is right outside your door. Salem has many historic landmarks and wonderful restaurants very close by. Come visit!!

Ocean Park Retreat

Bright and cheery 1 bedroom ground floor apartment with two+ car parking on quiet street in Marblehead's Ocean Park neighborhood, just steps from the ocean. Full size bed and pull-out full-size sofa in living room, private bathroom with in-floor heating, kitchenette with microwave, dishwasher, sink, double induction cook-top, refrigerator, and toaster oven. Laundry access. Walk to the waterfront, watch the sailboats drift by. Fifteen- minute walk to Historic town center.

Beachside Cozy Space-Near Boston/Airport/Train

Our space is a cozy second floor apartment just minutes from the city and airport. Less than 3 min drive and 5 min walk to train and beach. We strive to make our space feel like home. The space is perfect for 2 travelers. We provide all basic essentials, from coffee, toothpaste, towels, and a kitchenette NO stove. The space is completely private located on the second floor. You also will have a private balcony, complete with table and chairs!

City sanctuary - garden terrace - ocean view

Large sunny, private studio with stunning views and terrace overlooking the ocean, garden and JKF library, across the street from famous historic park Dorchester Heights. 2 blocks from beach. Close to convention center, airport, downtown, bus and trains. Easy walk to great local shops and haunts! Unit now equipped with Forbes #1 vetted best mattress - the Nectar Premier Hybrid Copper Queen mattress and there is a full size pull out futon