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Waterfront vacation rentals in Winthrop

Find and book unique waterfront accommodations on Airbnb

Quick stats about waterfront rentals in Winthrop

  • Total vacation rentals

    Explore 30 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 3,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Winthrop vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winthrop rentals

  • 4.9 Average rating

    Winthrop stays are highly rated by guests—averaging 4.9 out of 5!

  • Nearby attractions

    Winthrop’s top spots, include Orient Heights Station, Beachmont (MBTA station), and Suffolk Downs Station

Top-rated waterfront accommodations in Winthrop

Guests agree: these waterfront accommodations are highly rated for location, cleanliness, and more.

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Guest favourite
A comfortable living room features dark leather seating arranged around a round coffee table. Light curtains frame the windows, allowing natural light to brighten the space. A contemporary artwork hangs on the wall, complemented by decorative pillows on the sofas, enhancing the room's inviting appearance.
Apartment in Lynn

Spacious 2B Entire Home near Boston, Salem& Encore

Unwind at this spacious & stylish home near Boston & Encore Casino. Conveniently located in Lynn, it's 10 minutes away from Nahant and Revere Beaches, and 15 minutes from the historic town of Salem. The house was recently renovated, and is fully equipped with necessary amenities and items, for you to enjoy your stay & have fun exploring the nearby attractions with family & friends. Shops and restaurants are only a 5 minute drive away and the home is walking distance to public transportation

4.91 out of 5 average rating, 162 reviews
Top guest favourite
A vibrant flower pot filled with colorful flowers is positioned near a sparkling saltwater pool. In the background, ocean views are visible, complemented by lounge chairs and a hot tub. Gentle water splashes from the pool add a lively touch to the serene setting.
Apartment in Winthrop

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.

4.96 out of 5 average rating, 282 reviews
Top guest favourite
Condo in Winthrop

Truly Oceanfront! Spacious Family Petfriendly Home

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.

4.99 out of 5 average rating, 241 reviews
Top guest favourite
A private deck features comfortable green seating and a glass table, surrounded by colorful potted flowers. Ocean views extend beyond the railing, with trees visible in the background, creating a peaceful outdoor space for relaxation.
Apartment in Nahant

Ocean view studio with hot tub & access to Boston

All the amenities needed in a clean, spacious and modern apartment tucked away in a peaceful coastal town close to Boston. Studio with stunning ocean views, large private deck, hot tub, separate entrance, fast internet, granite kitchen, comfy couches, Breville Barista, bbq, and Sealy queen bed. Space is private with quiet residents in adjoining units. Off street parking. 2 sets of stairs to private entry, shared entrance by request. Use of hot tub at no additional cost. Short walk to beaches.

4.94 out of 5 average rating, 179 reviews
Top guest favourite
Home in Swampscott

Oceanfront stunning views, train to Salem & Boston

Relax at Casa de Mar, our 3 bedroom / 3 full bathroom oceanfront North Shore home with panoramic views of Swampscott Bay to Nahant. Walk to the train — downtown Salem in 7 min, Boston in 23 min. Enjoy a bright great room with 25’ ceilings, 70” TV, and modern kitchen. The master bedroom has a king bed, sitting area, TV, private balcony, and en suite bath. The first floor queen bedroom has a private balcony. The third queen bedroom has en suite bath. Perfect for family getaways and group trips.

4.93 out of 5 average rating, 140 reviews
Superhost
A spacious living area with a plush sectional couch in a neutral tone, centered around a coffee table, invites relaxation. Large sliding glass doors frame panoramic ocean views and provide natural light. A modern gas fireplace and stylish decor enhance the cozy atmosphere.
Apartment in Revere

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!

4.94 out of 5 average rating, 206 reviews
Top guest favourite
A calm waterscape is depicted, with smooth blue water reflecting soft clouds overhead. A distant island is visible on the horizon, surrounded by serene seas. Rugged rocks with lush green grass line the foreground, enhancing the tranquil coastal atmosphere.
Guest suite in Nahant

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.

4.96 out of 5 average rating, 217 reviews
Top guest favourite
A bright dining area features a wooden table surrounded by four white chairs. Large windows allow natural light to fill the space, while offering views of the waterfront. A comfortable seating arrangement is visible in the adjacent room, complete with a telescope for scenic observations.
Apartment in Swampscott

-> Front Deck Faces the Ocean! Ocean Breeze

Waterfront apartment with a spacious deck overlooking the ocean. Take it easy at this unique and tranquil one bedroom apartment with old world charm inside a mansion across from Kings Beach. Bright and open living room, dining area and updated kitchen with granite and stainless appliances. Bedroom has queen size bed. In the area of multiple beaches plus great dining. Half a mile to the commuter rail into Boston. Short drive to downtown Salem. Street Parking Only. Deck is shared

4.96 out of 5 average rating, 119 reviews
Top guest favourite
A serene winter landscape stretches across the view, showcasing a vibrant sunset reflected over a tranquil water surface. Snow covers the ground, while a shoreline with rocky formations is visible, framed by bare trees against the colorful sky.
Place to stay in Salem

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!!

4.96 out of 5 average rating, 284 reviews
Guest favourite
A light-filled living area features a pull-out sofa adorned with striped cushions and a coffee table with a decorative book and lamp. A sliding glass door opens to a sleeping area with a spacious bed, while bright curtains frame the window, offering a view of the exterior.
Guest suite in Marblehead

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.

4.91 out of 5 average rating, 316 reviews
Top guest favourite
A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.
Boat in Charlestown

2BR Spacious Yacht - Heat & AC- On Freedom Trail

The coolest way to stay in Boston: not a water view — you're ON the water. Carpe Diem II is a yacht in Charlestown Navy Yard with 2 queen staterooms, each with a private bathroom and shower, for up to 4 adults. Fall asleep to the harbor rocking you, have dinner and cocktails on the aft deck as boats cruise past, and stay comfortable with central A/C and heat. The Freedom Trail, North End, and Downtown are steps away. Hotels have views. You'll have the harbor.

4.96 out of 5 average rating, 156 reviews
Top guest favourite
An inviting outdoor seating area features a dark wicker sectional sofa and a round, patterned area rug. Potted plants add a touch of greenery. The entrance is marked by a black door with a window, and a sign indicates the listing number.
Guest suite in Winthrop

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.

4.94 out of 5 average rating, 1061 reviews

Popular amenities for Winthrop waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favourite
A living room features a fireplace surrounded by a brick wall, complemented by a cozy seating arrangement. Two armchairs and a sofa provide comfortable spaces for relaxation. Natural light enters through multiple windows adorned with lace curtains, illuminating the decorative rug underneath.
Apartment in Salem

House of Three Gables

4.99 out of 5 average rating, 391 reviews
Top guest favourite
A cozy living room features large windows that invite natural light, accented by a ceiling fan. Comfortable brown leather seating surrounds a dark coffee table, which holds magazines. A light-colored area rug complements the space, while a wall-mounted shelf displays decorative items.
Apartment in Salem

2-Bedroom Ocean View Walk to Beach and Downtown

5.0 out of 5 average rating, 156 reviews
Top guest favourite
An aerial view showcases a vibrant waterfront scene, featuring numerous boats anchored in the calm waters. Lush greenery frames the homes along the shore, while a sandy beach is visible nearby. The picturesque harbor area is complemented by a nearby dock and structures along the waterfront.
Apartment in Beverly

Seaside Getaway - Ocean Views

4.96 out of 5 average rating, 128 reviews
Top guest favourite
A well-lit sleeping area features a spacious bed adorned with soft linens and decorative pillows. Natural light fills the room from multiple windows, complemented by a cozy seating nook and shelving that adds a charming touch to the serene atmosphere.
Apartment in Salem

Winter Island Retreat

4.98 out of 5 average rating, 450 reviews
Superhost
Apartment in Salem

*New Spooky Downtown 2Br|Halloween+HocusPocus

4.88 out of 5 average rating, 152 reviews
Guest favourite
A cozy living area features a vibrant green sofa adorned with decorative pillows displaying tree motifs. A glass coffee table holds a globe, a stack of books, and a small decorative piece. Light filters through sheer curtains, illuminating the warm wood floors.
Apartment in East Boston

3BD Boston Skyline View, near Logan, Revere Beach

4.85 out of 5 average rating, 110 reviews
Guest favourite
A bench positioned on sandy beach overlooks a calm waterway, reflecting the sky's clouds and distant shoreline. The scene captures a peaceful outdoor environment, inviting visitors to relax and enjoy the serene landscape.
Apartment in Beverly

Enjoy Stunning Sunrises&Sunsets Ocean Views 33

4.89 out of 5 average rating, 168 reviews
Top guest favourite
A single-story home is set amidst lush greenery, showcasing a stone-accented facade and a spacious driveway. Skylights adorn the roof, and the property offers views of the adjacent lake, creating a serene lakeside atmosphere.
Apartment in Arlington

Lakeside apartment, patio, hot tub, outside shower

4.98 out of 5 average rating, 218 reviews

Waterfront house rentals

Top guest favourite
Home in Swampscott

Oceanfront I Decks I 4 Ensuite BRs I 35 min to Boston

4.93 out of 5 average rating, 115 reviews
Top guest favourite
The exterior of a contemporary two-story home is shown at dusk, featuring large glass windows and a wooden deck. Soft lighting emanates from the inside, highlighting the airy design. Leaf-strewn landscaping surrounds the house, enhancing its serene setting.
Home in Scituate

Stella Maris, 6 bedroom coastal home, water views

5.0 out of 5 average rating, 106 reviews
Guest favourite
An oceanfront backyard is showcased with comfortable seating arranged around a circular table. A hot tub is visible nearby, and additional seating is provided by lounge chairs. The expansive view of the ocean under a partly cloudy sky enhances the coastal atmosphere.
Home in Scituate

Oceanfront home w/Amazing Views, Hottub! Sleeps 10

4.94 out of 5 average rating, 100 reviews
Top guest favourite
A bright living area features floor-to-ceiling glass doors that frame scenic waterfront views. A cozy sofa is positioned alongside a wooden table with a potted plant. Sunlight streams in, highlighting the wood-paneled ceiling and warm oak flooring.
Home in East Boston

Waterfront Escape - Close to Airport & Downtown

5.0 out of 5 average rating, 58 reviews
Top guest favourite
A panoramic view of a sandy beach extends towards the ocean, with gentle waves lapping at the shore. A pathway leads from the foreground to the water, bordered by stone steps. The sky is partly cloudy, creating a serene coastal atmosphere.
Home in Hull

The Beach House, Crescent Beach

4.98 out of 5 average rating, 51 reviews
Top guest favourite
A serene coastal view showcases gentle waves lapping against a sandy beach, with distant silhouettes of the town under a softly colored sky at dusk. A winding road runs parallel to the shore, lined with parked cars, enhancing the tranquil atmosphere.
Home in Hull

4 bd Ocean View, Dual Deck, Beach Front Retreat

4.99 out of 5 average rating, 70 reviews
Guest favourite
Home in Weymouth

Bayfront Retreat with Private Ramp &Stunning Views

4.81 out of 5 average rating, 21 reviews
Top guest favourite
Home in Swampscott

Seaside Serenity

4.96 out of 5 average rating, 50 reviews

Waterfront condo rentals

Top guest favourite
A private bedroom features a spacious bed adorned with soft bedding in contrasting colors. Nightstands with lamps sit on either side. A vibrant neon sign is mounted on the wall, while the wooden ceiling beams add warmth. A colorful area rug completes the inviting space.
Condo in Salem

The Blue Suite, Private Parking Included

4.97 out of 5 average rating, 324 reviews
Guest favourite
A comfortable living area features a large sectional sofa with an orange accent pillow. A wooden coffee table sits in front, complemented by a light-colored media console housing a mounted TV. Natural light enters through multiple windows, illuminating the gray walls.
Condo in Beverly

Downtown Beverly| Water view| 2 BR| Steps 2 beach

4.93 out of 5 average rating, 126 reviews
Top guest favourite
This bright bedroom features two large windows that frame expansive views of the ocean and coastline. Natural light fills the room, highlighting the warm wooden floor and minimalistic decor. The space is designed for relaxation with a sense of tranquility from the scenic surroundings.
Condo in Revere

Newly renovated Boston Condo

5.0 out of 5 average rating, 44 reviews
Guest favourite
A sandy beach is visible from a balcony railing, with gentle waves lapping at the shore. Lush greenery and a few homes are in the background, while fluffy clouds drift across a bright blue sky, creating a serene coastal view.
Condo in Salem

Luxury Sandcastle Beach House Historic SALEM

4.94 out of 5 average rating, 31 reviews
Top guest favourite
The living area features a light wooden floor and is furnished with a soft white sofa and a wooden coffee table. Natural light enters through the windows and skylight. An entry door and a doorway to a bathroom are visible in the background, along with a cozy sleeping area with a bed.
Condo in Salem

Modern Seaside Penthouse Condo (Historic Salem)

4.97 out of 5 average rating, 60 reviews
Top guest favourite
A charming outdoor space features colorful Adirondack chairs arranged around a fire pit, surrounded by lush greenery. A flag gently waves in the breeze nearby. The serene waters are visible in the distance, reflecting soft hues from a sunset sky.
Condo in Salem

Salem Sanctuary by the Sea

4.91 out of 5 average rating, 34 reviews
Top guest favourite
A serene landscape showcases a sprawling marsh at sunset, with vibrant hues in the sky. Tall grasses and slender trees frame the scene, while a gentle waterway meanders through the lush greenery, providing a tranquil backdrop.
Condo in Essex

Marshside one-bedroom with stunning view

5.0 out of 5 average rating, 55 reviews
Guest favourite
The entrance features two tall nutcracker figures, dressed in vibrant red and blue, flanking the door. Green garlands and a wreath decorated with red accents adorn the black exterior, which is complemented by potted plants and bright red flowers.
Condo in East Boston

Eastie near the airport Great location

4.87 out of 5 average rating, 60 reviews

When is the best time to visit Winthrop?

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Avg. price$171 CAD$174 CAD$221 CAD$254 CAD$277 CAD$347 CAD$347 CAD$347 CAD$347 CAD$363 CAD$250 CAD$185 CAD
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