Apartment holiday rentals in Winthrop

4.94 out of 5 average rating, 175 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.

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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.

4.95 out of 5 average rating, 203 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!

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The spacious living room features hardwood floors with an orange accent wall and contemporary artwork. A comfortable sofa and decorative throw blankets are arranged around a coffee table adorned with seasonal decor. A faux fireplace adds a decorative touch, while a small bench provides additional seating.

4.89 out of 5 average rating, 246 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.

FamilyLocationSolo travel

4.88 out of 5 average rating, 149 reviews

A modern kitchenette is featured with stainless steel appliances, including an oven and refrigerator. A spacious gray sectional sofa is positioned on a geometric patterned area rug. Bright windows allow natural light to illuminate the room, complemented by decorative mirrors and a potted plant.

Apartment in Woburn

Newly Finished Guest Haven in Woburn

Welcome to our newly finished in-law lower level suite in Woburn! This private 1-king bed bedroom, 1-bath retreat features a cozy living room, a well-equipped kitchenette with a private entrance. Located on a quiet dead-end street, it’s just 5 minutes from Woburn Center, 15 minutes from Encore Boston Harbor, and a 20-minute drive to downtown Boston. Perfect for business travelers or couples, enjoy a peaceful stay with easy access to dining, shopping, and entertainment. Book your stay today!

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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, 144 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.

FamilyValueBeach

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.

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A historic clock stands prominently by the waterfront, marking the time against a beautiful sunset. The horizon features vibrant oranges and yellows as the sun descends. An open pavilion structure is visible in the background along the calm beach, reflecting a peaceful atmosphere.

4.83 out of 5 average rating, 100 reviews

Cozy Apt, minutes from Boston!

Welcome to this modern and cozy apartment, steps away from the first public beach in America. Perfectly located, 1 min to the Revere Beach T station, minutes from the airport, Salem, Encore casino, Universities, only 15 mins to Downtown Boston, and ideal location for quick access to all Boston has to offer. Perfect for families and groups.

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4.94 out of 5 average rating, 172 reviews

A scenic view captures a charming two-story white house overlooking the ocean, framed by a vibrant blue sky with scattered clouds. The foreground features a street with pedestrians, while vehicles are parked nearby. Greenery line the roadside, enhancing the coastal setting.

Apartment in Winthrop

Newly Renovated Ocean View 2 Bdrm Apt

Come relax in a newly renovated apartment with ocean view that sleeps up to 4 people (2 separate bedrooms & sofa bed in living room) w/ new kitchen & bathroom w/ top line appliances and walking distance to beach. TVs in every room will keep your friends / kids entertained and desk (w/ standing option) is ready if the office calls.

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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.

5.0 out of 5 average rating, 154 reviews

2-Bedroom Ocean View Walk to Beach and Downtown

Accommodates 4 comfortably. Walkable to bike trails, beaches, restaurants, an arcade, bike and kayak rental. Close proximity to downtown Salem. On-street parking.

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Popular amenities for Winthrop apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.97 out of 5 average rating, 426 reviews

A spacious living area features a high wood-beamed ceiling and large windows overlooking greenery. A comfortable couch and plush chairs are arranged around a coffee table. A staircase leads to a loft area, and a flat-screen TV is visible in the background.

Apartment in Roxbury

Light-Filled Luxury Apartment with View

ValueFamilyDecor

4.86 out of 5 average rating, 121 reviews

A cozy bedroom features a spacious bed adorned with a soft pink quilt and numerous plush pillows. Bedside lamps provide gentle lighting, while a small side table holds a lamp. A soft bench is positioned at the foot of the bed, enhancing the room's comfort.

Apartment in Swampscott

Vacation by the Sea

LocationFamilyTV

4.94 out of 5 average rating, 196 reviews

A comfortable living area is showcased, featuring a brown leather sofa and a wooden coffee table. A glass dining table with two chairs is positioned nearby. A flat-screen TV is mounted on a wall, with a kitchen area visible in the background.

Apartment in Dorchester

1 bed, 2 rooms, 4 guests Cute&new. Free parking

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Apartment in South Boston

An inviting living area features a navy blue sofa adorned with two patterned cushions, complemented by a round coffee table. Nearby, a dining set is visible beside a kitchen with stainless steel appliances, wood cabinetry, and ample counter space, illuminated by natural light from a window.

4.99 out of 5 average rating, 134 reviews

Extraordinary 1-Bedroom Apartment in South Boston!

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4.93 out of 5 average rating, 118 reviews

Apartment in Everett

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

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The main entrance features a large, ornate door with intricate glass designs that allow natural light to brighten the foyer. An American flag is displayed beside the door, and a small planter with white flowers sits at the base of the steps.

4.97 out of 5 average rating, 151 reviews

The 1870 Langmaid House Suite

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Private apartment rentals

4.91 out of 5 average rating, 128 reviews

A spacious living area features an exposed brick wall, wooden flooring, and ample natural light from skylights above. A small dining table and two bar stools are positioned near the modern kitchen, which includes essential appliances. Unique pendant lighting adds character to the room.

Apartment in Cambridge

Renovated 1-Bed w/ private deck

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A cozy deck area features red outdoor chairs arranged around a small table with a potted plant. Sliding glass doors provide a view into the living space, allowing natural light to brighten the area. The surrounding rooftops and greenery can be seen in the background.

4.88 out of 5 average rating, 162 reviews

* Safety & Comfort *Cozy & Clean 02 bedroom Apt.

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4.97 out of 5 average rating, 102 reviews

A modern kitchen is highlighted with white cabinetry and stainless steel appliances. A round wooden table with four upholstered chairs is positioned near the center, set with placemats. Bright overhead lighting enhances the open layout, revealing a view of additional kitchen features.

Apartment in Somerville

Lovely apt near Boston/Assembly Row/Encore Casino

LocationFamilyCheck-in

A vibrant bedroom is presented, featuring a gold sun mural on a purple wall. An ornate headboard supports a spacious bed adorned with an orange and colorful patterned blanket. Decorative artwork and artifacts add character, while a unique lamp provides soft lighting.

4.96 out of 5 average rating, 291 reviews

The Ghoul’s Attic-For 90s Witches and Wannabes

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Apartment rentals with a hot tub

4.92 out of 5 average rating, 233 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

ValueLocationKitchen

4.86 out of 5 average rating, 29 reviews

Apartment in Chelsea

Modern 2BR Retreat Minutes from Boston

LocationFamilyCheck-in

4.75 out of 5 average rating, 4 reviews

Apartment in Woburn

c. 1850 Farmhouse • Near Boston & Gillette

ValueFamilyBackyard