Holiday rentals with beach access in Winthrop

4.98 out of 5 average rating, 118 reviews

The exterior of a historic two-story building is shown, featuring blue siding and white trim. A tall tree stands at the front, providing shade, while a decorative fence encloses the property. Steps lead up to the entrance, enhancing the welcoming appeal of the home.

Condo in Winthrop

The Day-Burrill-Wadsworth-La Voix House

The Day-Burrill-Wadsworth-La Voix House is located in Winthrop, MA in the North Shore of Boston. Super close to Logan Airport for your traveling needs. A Level 2 EV Charger is available! This renovated 3 Bedroom penthouse apartment features a private roof deck, off-street parking, sunroom, and free in-unit laundry! A safe, spacious, and serene space. A historic building, it was one of the first handful of homes in Winthrop... built in 1860 (but since converted to two apartments and renovated).

4.97 out of 5 average rating, 345 reviews

The spacious bedroom features two queen beds with light green bedding, positioned beside a large window that allows natural light to fill the room. A modern bathroom is visible in the background, with neutral tones and elegant fixtures. Wooden benches provide additional seating.

Apartment in Winthrop

Private Suite• Pool • Sleeps 4 • Boston • Airport

Cody’s Place is a clean, comfortable stay mins from Boston, airport & beach - with heated pool & free parking. Thoughtfully hosted for a smooth, stress-free stay perfect for travelers, couples, or a quick getaway seeking convenience, comfort & prime location Private entry basement directly across from the ocean. Enjoy fresh sea air, sunrises & a restaurant steps away • Steps to beach • Mins to Airport • Boston access (ferry/Uber) • Free on-site parking • Fast WiFi + Smart TV • Easy self check-in

4.92 out of 5 average rating, 1396 reviews

A cozy living area showcases a light-colored sofa adjacent to a white coffee table with a puzzle setup. A small dining table with two wooden chairs is positioned nearby. A bright entrance door provides natural light, and shelves display maritime-themed decor.

Guest suite in Winthrop

Licensed Boston airport studio 5 stars, subway

We are a licensed & permitted Airbnb in the Boston area, ensuring a safe, reliable experience for all our guests, meeting safety & inspectional standards. Flexible early/late check in/out, please advise us of your expected check in and check out times so we can better accommodate you & your travel plans. Normal check in 3pm, normal check out 11am. Please let us know if you need parking, we provide free off street parking during your stay. Window AC in the summer. Looking forward to hosting you.

4.96 out of 5 average rating, 281 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.

4.99 out of 5 average rating, 240 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.

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.

4.94 out of 5 average rating, 206 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!

4.98 out of 5 average rating, 504 reviews

The exterior of the private studio is shown, featuring a light blue siding with a gray shingled roof. A welcoming front door is flanked by a light fixture and a decorative sign. Flowering plants are arranged in front, enhancing the outdoor space.

Cottage in Winthrop

J&K's BnB .... Private studio Airbnb with parking

Our non-smoking private Studio Bnb is located by the airport in Point Shirley; a small safe seaside community. Daily continental breakfast is provided. No cooking allowed, kitchenette with a microwave, coffee maker, a refrigerator. Private bathroom with corner shower, free 5G wireless WiFi, RokuTV, one car off-street parking. Due to our severe medical health allergies to animal hair, fur & feathers, Airbnb has granted us an exemption not to host guests service or emotional support animals.

4.88 out of 5 average rating, 248 reviews

Stunning Oceanview-4 Train Stop Logan Airport

Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

4.78 out of 5 average rating, 239 reviews

A stone sign marked 'BEACHMONT' stands prominently at the entrance of a landscaped area. Surrounding features include a stone-paved pathway, a bench, and several tables. Lush greenery lines the background, providing a natural backdrop to the welcoming space.

Home in East Boston

Renovated Cozy City Getaway

Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

4.85 out of 5 average rating, 130 reviews

A well-lit dining area features a wooden table surrounded by chairs, complemented by a decorative chandelier overhead. The open layout allows for a view into the comfortable living area, where soft seating and natural light create a relaxed ambiance.

Home in Winthrop

Sunny 3 bedroom on beach

Welcome to our beautiful 3 bedroom apartment on the beach! Enjoy stunning ocean views and easy access to Winthrop Beach, only 2 minutes away. Accommodations for up to six guests, making it perfect for families or groups of friends. Bright and airy living area with plenty of natural light and a cozy seating area, perfect for relaxing after a long day at the beach. The dining area offers ample seating, and the fully equipped kitchen, private deck with breathtaking views of the ocean.

The living room features two sofas, one in a solid color and the other with a striped pattern, facing a large window that offers ocean views. A light-colored area rug lies on the wooden floor, and a simple coffee table is centered in the space.

4.95 out of 5 average rating, 148 reviews

2 Bedroom Apartment with Ocean Views

Quiet, newly renovated 2 bedroom apartment just outside Boston 180 degree ocean views 10-15 min walk to subway with quick access to Goverment Center, MGH, Aquarium, North End and TD Garden. Beach access accross the street and short walk to Revere Beach. Lots of good resturaunts and cafes nearby. Unit is located on the 3rd floor. 3 sets of stairs to access apartment. Perfectly safe but not handicap accessible or convenient for anyone with impaired mobility or small children.

4.96 out of 5 average rating, 112 reviews

The exterior of a stylish two-family home is depicted, featuring a welcoming porch with white railings and a neatly landscaped front yard. Flowering plants, small trees, and a paved pathway lead to the entrance. The upper floor includes strategically placed windows, allowing natural light to filter in.

Apartment in Winthrop

Pleasant Place 2

This stylish place to stay is perfect for a single person or couple. It is a very beautiful space in a lovely 2 family, owner occupied home. Winthrop is a beautiful oceanside residential community situated at the entrance of the most beautiful harbors in New England. Winthrop offers small town suburban living, within minutes to Boston. We have public transportation to downtown Boston in about 20 minutes, Logan Airport in 15 minutes. We also have a Ferry Service to Boston.

Popular amenities for Winthrop Accommodation with Beach Access

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.94 out of 5 average rating, 177 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

A spacious bedroom features a large bed dressed in white sheets and a light blue blanket. Nightstands with lamps are positioned on either side of the bed. A subtle area rug adds warmth, while a painting hangs on the wall, complementing the calm color scheme.

4.96 out of 5 average rating, 163 reviews

Spacious 3 Bedroom Apartment with King Bed

A light-filled corner of the living area features a sectional sofa in soft gray, complemented by a small coffee table. Three windows dressed in blinds allow natural light to filter in, enhancing the cozy and inviting atmosphere.

4.93 out of 5 average rating, 256 reviews

Quiet Neighborhood Luxury Stay

4.93 out of 5 average rating, 223 reviews

An air hockey table is centered in a bright, modern room. The table's glossy surface features distinct markings for gameplay. To the side, a simple plant and a decorative white vase complement the clean aesthetic of the space.

Apartment in Lynn

Modern & Cozy Apt close to Boston and Salem

4.93 out of 5 average rating, 121 reviews

An updated kitchen features granite countertops, white cabinetry, and stainless steel appliances. A large island with seating for four is complemented by a dining nook with natural light. Potted plants add a touch of greenery, enhancing the inviting kitchen space.

Apartment in Hull

Coastal Cottage Home

A modern kitchen space features a central island with a seating area, complemented by wooden cabinetry and essential appliances. A staircase leads to the upper level, while decorative accents, including wall art and plants, enhance the inviting atmosphere.

4.73 out of 5 average rating, 248 reviews

Superb urban community Apartment

4.97 out of 5 average rating, 117 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

4.97 out of 5 average rating, 118 reviews

A spacious window with dual openings frames a view of the ocean and sandy beach across the street. The interior walls are painted in a calming blue, complementing the natural light that fills the room. Grassy areas can be seen in the foreground.

Apartment in Nahant

The Blue Pearl

Holiday House Rentals with beach access

4.95 out of 5 average rating, 137 reviews

A spacious living room features a large gray sectional couch complemented by a sleek wooden coffee table. An accent chair provides additional seating. Striped rug adds a touch of pattern to the hardwood floors. A gallery wall displays various posters, and a flat-screen TV is mounted nearby.

Home in Lynn

Private Cozy Third Floor Space

4.97 out of 5 average rating, 148 reviews

An open eat-in kitchen features sleek white cabinets and a dark countertop. The kitchen island, which seats three on mint green stools, is set with dishware. Natural light filters through the window shades, complementing the modern appliances and warm color tones.

Home in Everett

Top 10% Stay | Sleeps 6 | Easy Boston Access

4.97 out of 5 average rating, 149 reviews

Home in Hull

Walk to Nantasket Beach-Retro Cottage with Parking

4.93 out of 5 average rating, 140 reviews

Home in Swampscott

Oceanfront stunning views, train to Salem & Boston

4.91 out of 5 average rating, 172 reviews

The living room features a cozy arrangement of soft gray sofas adorned with decorative pillows. A rustic brick fireplace is framed by a wooden mantel, above which a large flat-screen TV is mounted. A round coffee table sits at the center, complemented by a light-colored area rug.

Home in Revere

Spacious and Luxurious House

4.98 out of 5 average rating, 181 reviews

A spacious living area showcases a modern leather sofa facing a wall-mounted television. Natural light filters through large windows, creating a bright atmosphere. A dining table with light-colored chairs is positioned nearby, with a decorative plant placed in the center.

Home in Marblehead

Walk To Everything

5.0 out of 5 average rating, 148 reviews

A charming farmhouse exterior is showcased, featuring a weathered wooden facade and bright blue shutters. A welcoming front porch is adorned with pumpkins, while well-maintained landscaping and a mailbox are visible in the foreground.

Home in Scituate

Cozy, well-equipped beach cottage, steps to beach!

Superhost

An airy living space features high ceilings with slanted angles and large windows allowing natural light to filter in. Wooden floors are complemented by simple furnishings, including a dining table with chairs and a bright arrangement of flowers. Nearby, cabinets provide ample storage.

Home in Jamaica Plain

4.89 out of 5 average rating, 180 reviews

Now availJamaica Plain & Arboretum 20min toBoston

Holiday condos with beach access

4.99 out of 5 average rating, 142 reviews

A dining area features a dark wooden table surrounded by four chairs, illuminated by a modern chandelier. Light enters through large windows with sheer white curtains, revealing glimpses of a vibrant outdoor view. A colorful area rug adds warmth to the hardwood floor.

Condo in Swampscott

Newly Renovated Victorian close to Salem

4.97 out of 5 average rating, 250 reviews

A cozy living space features a queen bed with an orange throw blanket, complemented by natural light filtering through double windows. A mounted TV is positioned above a brick fireplace, while a comfortable sofa and a coffee table enhance the inviting layout.

Condo in Salem

The Green Suite, Private Parking Included

4.99 out of 5 average rating, 151 reviews

An open-concept living and dining area is showcased, featuring a wooden dining table with chairs, a comfortable sofa, and a flat-screen TV mounted on the wall. Natural light enters through multiple windows, enhancing the bright and airy feel of the space.

Condo in Marblehead

Samuel Tucker House - Downtown Luxury 2 Bed Condo

4.98 out of 5 average rating, 209 reviews

A comfortable living room features a soft gray sofa flanked by two armchairs. A round coffee table sits in the center, adorned with a decorative bowl. Natural light enters through a window adorned with white shutters, and a cozy rug enhances the inviting ambiance.

Condo in Marblehead

Harbor Hideaway

Superhost

A modern kitchen features white cabinetry with a gray island and two black bar stools. Stainless steel appliances, including an oven and refrigerator, complement the light countertops. Pendant lights hang above the island, illuminating the space, while natural light streams through the window.

Condo in East Boston

4.89 out of 5 average rating, 198 reviews

Luxury Condo in Boston w/ backyard & parking

4.94 out of 5 average rating, 106 reviews

Condo in Swampscott

Ocean View Coastal Retreat | Walk to Beach | Salem

4.96 out of 5 average rating, 164 reviews

A spacious living room is showcased with large windows offering natural light. Comfortable seating includes a light green sectional sofa and a white couch. A wooden coffee table sits atop a colorful area rug. A flat-screen television is mounted on the wall, providing entertainment options.

Condo in Dorchester

1st floor, free parking off street, 3 min to train