Waterfront vacation rentals in Winthrop

4.96 out of 5 average rating, 286 reviews

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.

4.98 out of 5 average rating, 221 reviews

Apartment in Arlington

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.

4.99 out of 5 average rating, 242 reviews

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.

4.95 out of 5 average rating, 182 reviews

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.

4.93 out of 5 average rating, 144 reviews

Home in Swampscott

Oceanfront Retreat | Salem 7 min by train

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.

4.94 out of 5 average rating, 211 reviews

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!

4.96 out of 5 average rating, 290 reviews

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. There is offstreet parking for up to two cars. You can walk to four beaches within minutes, one is right outside your door. Salem has many historic landmarks Come visit!!

4.96 out of 5 average rating, 221 reviews

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.

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.

4.99 out of 5 average rating, 394 reviews

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!

Guest suite in Marblehead

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.

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, 320 reviews

4.96 out of 5 average rating, 159 reviews

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.

4.94 out of 5 average rating, 1071 reviews

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.

Popular amenities for Winthrop waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.88 out of 5 average rating, 156 reviews

*Spooky Halloween 2Br|Hocus Pocus+Downtown Salem*

4.96 out of 5 average rating, 122 reviews

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

4.91 out of 5 average rating, 165 reviews

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

4.85 out of 5 average rating, 110 reviews

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

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.

4.98 out of 5 average rating, 455 reviews

Winter Island Retreat

4.98 out of 5 average rating, 207 reviews

Mariam’s On Becket

4.96 out of 5 average rating, 137 reviews

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

4.91 out of 5 average rating, 119 reviews

An aerial view captures the vibrant coastal town, revealing a marina filled with boats and colorful buildings lining the waterfront. Lush greenery complements the serene blue waters, while a bridge connects the landmasses. The landscape showcases the harmonious blend of nature and community.

Apartment in Beverly

Water View Apartment in Beverly

Waterfront house rentals

5.0 out of 5 average rating, 107 reviews

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, 59 reviews

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

4.99 out of 5 average rating, 71 reviews

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

4.96 out of 5 average rating, 53 reviews

Home in Swampscott

Seaside Serenity

4.98 out of 5 average rating, 52 reviews

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

5.0 out of 5 average rating, 9 reviews

Home in Scituate

Luxury Listing! Elegant Oceanfront Escape

4.86 out of 5 average rating, 29 reviews

Home in Scituate

Wavehouse | Oceanfront Getaway on Private Beach

5.0 out of 5 average rating, 6 reviews

Home in Medford

Riverfront Boston Retreat w/Parking & Backyard!

Waterfront condo rentals

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.

4.97 out of 5 average rating, 329 reviews

The Blue Suite, Private Parking Included

4.93 out of 5 average rating, 130 reviews

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

5.0 out of 5 average rating, 44 reviews

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

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.

4.94 out of 5 average rating, 32 reviews

Luxury Sandcastle Beach House Historic SALEM

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.

4.92 out of 5 average rating, 36 reviews

Salem Sanctuary by the Sea

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.

4.97 out of 5 average rating, 63 reviews

Modern Seaside Penthouse Condo (Historic Salem)

5.0 out of 5 average rating, 57 reviews

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