Beachfront vacation rentals in Winthrop

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Winthrop

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Weymouth

4.94 out of 5 average rating, 124 reviews

Newly remodeled home with ocean views!

Spacious home newly remodeled with all high end touches. This house has views of the Boston skyline and harbor Islands. Each bedroom and floor has it's own split system air conditioning for maximum comfort. Preferred neighborhood of North Weymouth which is 10 miles from Boston. This house provides a convenient location for you and your family to explore the city with all the comforts of home. Full laundry facilities are on the same floor with the bedrooms. 2 decks to relax and enjoy the views.

Top guest favorite

Apartment in Winthrop

4.96 out of 5 average rating, 236 reviews

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.

Guest favorite

Apartment in Hull

4.9 out of 5 average rating, 42 reviews

Brand new ocean front apartment on Nantasket Beach

Direct water front development, Owners unit with a wrap around balcony that has magnificent ocean views on one side and beautiful sunsets over looking Worlds End and the Bay on the other side. This is a brand new custom apartment in a new luxury apartment buiIding. Step outside, be on Nantasket Beach, one of the most beautiful beaches in the state. Walk to great restaurants, The Paragon Boardwalk and Beer Garden. Visit the Swedish candy store on the 1st floor or see live bands at the C-Note.

Top guest favorite

Condo in Winthrop

4.99 out of 5 average rating, 180 reviews

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.

Top guest favorite

Apartment in Beachmont

4.99 out of 5 average rating, 108 reviews

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!

Top guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 283 reviews

PrivateBeach for 2 Adults, Gloucester MA SquishInn

SquishInn & SplashLanding are quiet, couples beach getaways. 2 adults/unit. No pets. Enjoy the pristine 1 1/4 mile private beach on our beach chairs/towels. SquishInn - hotel room-style unit. Large walk-in shower, vanity, private toilet, small sized refrigerator, Keurig & micro. FULL access to private beach & off street parking. * Combine w/ SplashLanding for a full kitchen, oceanside deck & accommodations for 4 adults. Splashlanding: copy and paste airbnb.com/h/splashlanding-gloucester-ma

Guest favorite

Home in Gloucester

4.97 out of 5 average rating, 117 reviews

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).

Guest favorite

Apartment in Rockport

4.94 out of 5 average rating, 178 reviews

Mary's By The Sea

A unique 650 square foot ground floor apt across the street from Front Beach. 6 minute walk from the Rockport MBTA . There is a separate bedroom with a queen mattress and a pullout sofa bed in the living area. The pullout sofa is best for teens or smaller kids .There is a bathroom with a sink and toilet. There is another room with a sink and shower. The kitchen area is more like a kitchenette than a full-size kitchen. We provide one parking spot next door at The Cove parking lot.

Top guest favorite

Home in Rockport

5 out of 5 average rating, 14 reviews

Adorable renovated house, steps from Front Beach

This charming home was recently fully renovated. The brand new kitchen features stunning granite countertops and stainless steel appliances. The large living/dining room features a 55" flat-screen TV comfy seatingnd a dining table for 4. There is a king bed in the Master Bedroom, along with a TV, ceiling fan, and air conditioning. The second bedroom has a twin daybed, with a second twin trundle bed underneath. The backyard features a patio with a seating for 4 and a gas grill.

Superhost

Guest suite in Winthrop

4.85 out of 5 average rating, 111 reviews

The Strand on the Beach

Welcome to the 129 The Strand! This accommodation will transport you to a tropical paradise where you can relax and enjoy the sun, sand and sea. Located a few steps from the beach, our Airbnb is the perfect place for your dream vacation. The interior is decorated in a modern and cozy style, and is equipped with everything you need for a comfortable and relaxed stay, it has 1 bed, 1 bath, living room, private entrance, parking, & refrigerator.

Guest favorite

Home in Marshfield

4.96 out of 5 average rating, 24 reviews

The Lily Pad

Beautiful beachfront property overlooking Brant Rock. Just steps away from various restaurants and bars. Very lively atmosphere. House is completely remodeled . Private access to the beach . A great place to enjoy making memories, watch beautiful sunrises and sunsets from comfort while having a cup of coffee or practice yoga on the beach while watching the visiting seals.

Top guest favorite

Townhouse in Gloucester

5 out of 5 average rating, 172 reviews

Between 2 Beaches

This 3 level, 3 bedroom, 2.5 baths, recently renovated beach themed, fully stocked condo, has 2 unique outdoor spaces, and is located within walking distance right in between 2 of the most amazing beaches in Cape Ann: Good Harbor Beach in Gloucester, and Long Beach in Rockport. Take your pick, no need to drive and pay to park, it's just a short to walk to either.

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What guests are saying

Winterfell - Beautiful Beachhouse (Private Beach!)

4.93 out of 5 average rating, 71 reviews3 months ago

Tommy was great. He was easy to contact and communicated wonderfully. The house was set up for a guest with everything you needed for a comfortable stay. The furniture and beds were so comfortable as well as the welcoming feel. Plenty of spacious rooms. Even spaces you could have alone time. When they described the house on the ocean, it really is. This was by far the best Airbnb we’ve stayed at. Hope to rent it again next year. I can’t say enough on how comfortable the house is. This is the first house we’ve recommend for other people to stay at. Peg

Home in Marshfield

What guests are saying

The Haabah Beach Retreat—4 Minute Walk to Beach

4.91 out of 5 average rating, 34 reviews32 months ago

Everything was just as we expected - wonderful! It really is a 4 minute walk to the beach! The bedrooms were lovely and the beds comfy. The kitchen equipment and dishes were great- full sets of plates, utensils, knives, pots and pans, etc. We grilled most every night and enjoyed the private area out side. Other nights we ate in restaurants in Gloucester, which is a cute town with shops and a museum on the waterfront. Rockport is just a few minutes away and makes for a fun afternoon of poking around shops. M Russell is very responsive to questions. All the communications were great. We were on a vacation with our 2 adult kids and their partners. Everyone had a great time.

Townhouse in Gloucester

What guests are saying

Charming condo steps from beach

4.86 out of 5 average rating, 14 reviews1 month ago

I can’t rave enough about how wonderful our stay was. Casie was absolutely great. She made sure our stay was perfect from the beginning to the end. The location is amazing. There are restaurants and the beach that are walking distance. Winthrop is a true gem! We are looking forward to coming back and staying here again!

Apartment in Winthrop

What guests are saying

Oceanfront w/Amazing Views! Hottub! Location!

4.98 out of 5 average rating, 51 reviews1 week ago

It’s rare to have a place match pictures exactly how it’s depicted in the App. No camera tricks, what you see is what you get. You could fall into the ocean, it’s that close. Awesome falling asleep to waves each night of our stay. Game table provided hours of fun during the evening hours with the family. Mill Wharf restaurant and downtown scituate within a 5 minute drive was great. Very friendly neighbors as well. Will def be back.

Home in Scituate

What guests are saying

3 bdr, steps from the ocean, minutes from Boston

4.8 out of 5 average rating, 10 reviews5 days ago

This was a beautiful bnb right by the water. There were so many local food spots to eat at as well. The place was very clean and cozy, the perfect place to stay away from the city but close enough to get to and from without issue. I would definitely stay here again, thank you for allowing us to stay in such a beautiful home!

Home in Winthrop

What guests are saying

Back Beach Cottages

5 out of 5 average rating, 21 reviews8 months ago

We had a very nice stay at the “Back Beach Cottages” Both cottages were well equipped and had everything you would need to feel at home. Beach chairs and towels were a definite plus and we really enjoyed the Sunday night concert from the deck. Lots of restaurants and shops within walking distance as well as two lovely beaches. Meghan was very responsive prior to and throughout our stay. The view was better than expected and seeing the sunrise from the cottage was a highlight of our trip.

Cottage in Rockport

What guests are saying

Large Oceanfront Home - VIEWS - Sleeps 12.

4.81 out of 5 average rating, 26 reviews3 months ago

Anne’s place is an amazing old ocean front home. I was so excited to experience staying there, as we have no houses like this where I’m from. The ocean views are amazing from the porch, the upstairs bedrooms, and the crow’s nest. We watched seals and eider and mergansers and loons. It was also great to people watch from the front porch as lots of dog walkers walked by. We rock scrambled at low tide and got out to Brant Rock. Anne was super responsive and quick to answer questions when we first checked in. The house is old, quirky, and beautiful. The updated bathrooms are gorgeous. We cooked breads and lasagna and lots of other stuff and had all the pots, pans, and baking pans that we needed (which is rare in an Airbnb). Really lovely stay in a really lovely home. The perfect place to ring in the New Year with people I love.

Home in Marshfield

What guests are saying

Anchors Away Inn Cozy Walk to Beach, Courtyard

4.96 out of 5 average rating, 68 reviews1 month ago

A nice little apartment close to the beach! I liked the fire pit and the grill especially. The beds were very soft and had a lot of warm blankets. The TV has a lot of wifi capability. The kitchen comes fully stocked with dishes and cookware. The neighborhood is calm and the sea breeze is nice, even if it's chilly out. Fencing around the property gives a lot of privacy in the back yard, and there are chairs out there if the weather permits chilling outside.

Apartment in Hull

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