Apartment holiday rentals in Winthrop

4.99 out of 5 average rating, 174 reviews

Apartment in Billerica

Air Bee-n-Bee Hive– Unique Themed Creative Retreat

Plan a unique and memorable stay at the Hive, a bee-themed apartment in a Boston suburb 21.1 miles from the city. Delight in the charming honeybee-inspired décor. Relax on the patio and enjoy the nearby chickens and geese – and especially their fresh eggs. You’ll love the entertainment options – 100s of free movies plus cable TV and access to streaming channels. Everything you need is here, from a full kitchen with a coffee bar to EV charger. Got work? A workspace and super-fast Wi-Fi await you.

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.

4.97 out of 5 average rating, 333 reviews

Cody's Place Boston Airport Pool/Beaches ParkFree

Retreat, relax, & refresh in your own private entry basement in law apartment of our well bunkered Beach House. BEST LOCATION across from the mighty Atlantic & Iconic Winthrop Arms Hotel/Restaurant. Take in the salty air & breathtaking sunrises. Steps from Ocean Sunrise & Sandy Beach Surf. Walking distance to public transport, restaurants, parks, or Uber/Walk to the center bars & other attractions. Vacation living. Ferry minutes to downtown Boston. 1 of 3 officially licensed AirBnB's in town.

4.75 out of 5 average rating, 137 reviews

A spacious sleeping area features a bed with a neutral white bedspread. Bedside tables with lamps are positioned on either side of the bed. Natural light filters through sheer curtains, illuminating the hardwood floors and an area rug with a subtle pattern.

Apartment in East Boston

Studio in East Boston #1

Peaceful and comfortable studio located in East Boston, Ma! It is located 10 mins away from the airport and 15 away from downtown Boston. It is also a 2 min walk from the train station. Guest will have full access to this studio which offers a bedroom, bathroom and kitchen area. Airport train station (10 mins), free shuttles to terminals. Kids under 3 years old don’t count as a guest. We offer a pack n play with a mattress! There is NO SMOKING inside the apt or hallways, fine will be charged.

4.87 out of 5 average rating, 172 reviews

A studio space features a spacious bed with a decorative coral blanket and neatly arranged towels. A dining table with two chairs sits adjacent to a kitchenette equipped with basic appliances. Light wood flooring complements the overall layout, which is brightened by overhead lighting and wall decor.

Apartment in South End

Walk everywhere! Location! Location! Cute studio!

Walk everywhere! Can you believe this location? 4 minutes from subway stations and in the middle of everything. This studio is located in the heart of Boston. Walking distance to the T stations of Symphony and Hynes Convention Center. Right between South End and Back Bay. Very close to Christian Science Plaza, Prudential Center, restaurants, bars, Fenway Park, plenty of local stores, and more. Includes everything you'll need for your stay. Super safe and one of the best neighborhoods in town.

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.

4.96 out of 5 average rating, 265 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.

4.87 out of 5 average rating, 551 reviews

The exterior of a Victorian home is showcased, featuring a light-colored facade with decorative trim. A welcoming porch area is accented by potted plants, and steps lead up to a wooden front door flanked by tall windows. Lush greenery surrounds the property.

Apartment in Newtonville

Country Charm minutes from the Hub - 1st Floor Apt

Private, smoke/pet-free 1st floor efficiency apartment with independent access for ONE PERSON ONLY at back of family home. Includes full bathroom, refrigerator, microwave, coffee maker + WiFi. All basic supplies provided. Driveway parking. Mins from MBTA transit including commuter rail. Laundry-room access for rentals of 7 nights ore more. Sorry, no vaping and no smokers - even if you smoke outside - because smoke odor on you or your clothes can be left in your wake in the room. No open flame.

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.

4.96 out of 5 average rating, 167 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!

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, 227 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.

4.97 out of 5 average rating, 407 reviews

The exterior of the 1850s home is showcased, featuring a modernized grey facade with white trim. A tree stands nearby, casting shadows on the manicured lawn. Brick pathways lead to the entrance, where a welcoming dog is seen in the foreground.

Apartment in Salem

The Salem House Too

An 1850’s built home with a modern interior and revitalized exterior. It’s the perfect spot to relax and unwind or take work on the road. Located one mile from downtown Salem and away from the traffic, our goal is to provide a classy, upscale experience with all of the comforts of home. Pair a sparkling clean private space with off street parking, unlimited coffee, and a fridge stocked with drinks and snacks and you’ve got The Salem House! Come stay with us and see what Salem is all about!

4.99 out of 5 average rating, 154 reviews

An inviting living area features a grey recliner and a brown sofa, arranged on an orange and grey patterned rug. A large TV is mounted on the wall, while a dining table is visible in the background surrounded by chairs. Natural light filters through the windows.

Apartment in Medford

Couples Retreat - Apt in Charming Colonial Home

Newly renovated, open concept apartment in a private home located on a quiet residential street. Single, queen-sized adjustable bed, steam shower, and oversized bubble jet tub make this an ideal retreat for stress free relaxation. Includes off-street parking, full-size washer and dryer, and the use of both front and rear porches with seating in season. This apartment is great for couples or individuals looking to relax and get a break from their busy lives.

4.93 out of 5 average rating, 427 reviews

A spacious living area is furnished with a dark sofa, a decorative wall art piece, and a round coffee table. Bar stools are positioned near the kitchen, which is visible in the background. Natural light enters through windows covered by green curtains.

Apartment in Dorchester

Apartment 1BR mins from JFK/UMASS free parking

Airbnb Superhost offering meticulous and spacious 1 bedroom 1 bath, queen bed plus sleep sofa and airbed (please request it when booking). Free street parking or in the driveway, free laundry, full kitchen, hardwood and tile floors. Wireless internet, smart TV. 10 min walk to Red Line JFK/UMass station and Savin Hill station. Free parking on the street or in our driveway. Well kept front yard and back yard with porch, chairs and table.

4.87 out of 5 average rating, 365 reviews

A cozy living space features a light-colored sectional sofa in front of a wall-mounted television. A framed artwork decorates the white walls, and a small round table sits between a patterned area rug and the sofa, adding comfort to the setting.

Apartment in Stoneham

Entire guest suite in Stoneham

Come enjoy this quiet and comfy home in the heart of Stoneham—your perfect getaway just 20 minutes from the airport and the historic city of Boston. Conveniently located near shopping malls, restaurants, coffee shops, grocery stores, and the natural beauty of Middlesex Fells Reservation and Stone Zoo, this peaceful retreat is designed to make your trip relaxing, enjoyable, and stress-free.

Popular amenities for Winthrop apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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.

4.98 out of 5 average rating, 87 reviews

Pleasant Place 2

A spacious dining area features a wooden table surrounded by white chairs. A sideboard is positioned against the wall, complemented by decorative elements. Natural light enters through two windows, illuminating the hardwood floor. A cozy seating area can be seen through a large mirror.

4.88 out of 5 average rating, 49 reviews

Skyline view spacious 3bd close Boston/beach/Airpt

A modern living area features a sectional sofa with a textured blue fabric, positioned on a patterned rug. A bright kitchen is visible in the background, showcasing wooden cabinetry and stainless steel appliances, while large windows allow natural light and views of the outdoors.

4.82 out of 5 average rating, 115 reviews

Luxurious 2BR w/ Pool, Gym & W/D, nr Blue Line,

4.88 out of 5 average rating, 116 reviews

A modern living area showcases a grey sectional sofa, complemented by a geometric area rug. A small coffee table sits in front, and a desk with a chair is positioned nearby. Large windows provide natural light, and a cityscape photograph adorns the wall.

Apartment in East Boston

1 BR Gem 5min to Train & Airport explore the city

An open living area features warm wood floors and neutral-colored walls. A large dining table is surrounded by white chairs, with a light fixture above. A television is mounted on the wall opposite a comfortable sofa, complemented by a decorative plant and a textured area rug.

4.9 out of 5 average rating, 40 reviews

Charming condo steps from beach

The living room features a spacious dark sectional sofa with a leopard-print accent, positioned on polished hardwood floors. A large projection screen displays colorful images on the wall, while glass doors lead to the private deck, allowing for natural light and ocean views.

4.96 out of 5 average rating, 24 reviews

Boston Beach Pad Logan Airport

4.95 out of 5 average rating, 44 reviews

The living area features a modern gray sofa paired with a mustard armchair, surrounded by wall art and warm lighting. A circular coffee table sits in the center of the space, complemented by a television mounted on the wall and a decorative plant nearby.

Apartment in Revere

Top 5% Stay | 3-Min to Beach & Train | Hotel Beds

4.92 out of 5 average rating, 26 reviews

Apartment in Revere

Marian place

Private apartment rentals

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, 150 reviews

Spacious 3 Bedroom Apartment with King Bed

Apartment in Lakeside Marblehead

An inviting outdoor deck features a seating arrangement with matching dark wicker chairs and a lounge chair, surrounded by vibrant flower pots. The entrance is framed by a dark door, and large windows allow natural light to brighten the space.

4.96 out of 5 average rating, 307 reviews

Mid Town Marblehead 1 B/R Pvt. Wing w/Own Entrance

4.98 out of 5 average rating, 423 reviews

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

4.88 out of 5 average rating, 638 reviews

A cozy living space features a gray sofa adorned with patterned cushions and a black coffee table. A vibrant yellow wall adds brightness to the room, while natural light filters through a window covered by sheer curtains. A spiral staircase leads to additional living areas.

Apartment in Charlestown

3 bed apt next to T- fast wifi-off street parking

4.94 out of 5 average rating, 164 reviews

A cozy living space features exposed brick walls complemented by warm wooden accents. A spacious sectional sofa is arranged around a circular coffee table, adorned with a vase of flowers. Nearby, framed artwork is displayed on the wall, adding character to the room.

Apartment in East Boston

Quiet brownstone close to city

4.92 out of 5 average rating, 104 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 Home Walk to Beach

4.94 out of 5 average rating, 158 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 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.

4.92 out of 5 average rating, 243 reviews

Quiet Neighborhood Luxury Stay

Apartment rentals with a hot tub

4.93 out of 5 average rating, 186 reviews

A private outdoor area features a spacious hot tub surrounded by wooden walls and deck flooring. Soft lighting is provided by string lights overhead. A small table sits nearby for convenience, and a patterned rug adds a touch of comfort to the space.

Apartment in Woburn

Your Cozy 1 BR Apt & Relaxing Retreat

5 out of 5 average rating, 6 reviews

An outdoor deck features a spacious dining table surrounded by black chairs, complemented by an umbrella. Potted plants and garden beds add greenery, while a view of tree foliage can be observed in the background. The deck provides an inviting space for outdoor dining.

Apartment in Lynn

5 Mi to Salem! Lynn Apt By the Sea w/ Hot Tub

4.75 out of 5 average rating, 4 reviews

Apartment in Woburn

c. 1850 Farmhouse 8mi. from Boston-close to Salem

4.81 out of 5 average rating, 27 reviews

A well-lit common area features a billiards table at its center, surrounded by comfortable seating. Large windows allow natural light to fill the space, accentuating the hardwood flooring and a decorative rug. A bookshelf showcases a variety of items and books, adding character.

Apartment in Revere

Step Into Spacious Vintage Charm in West Revere

5 out of 5 average rating, 5 reviews

Apartment in Chelsea

4Bed AP/5 min walk to T-Logan- downtown to Boston

4.98 out of 5 average rating, 204 reviews

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

4.54 out of 5 average rating, 145 reviews

A jacuzzi is positioned on a deck overlooking the water, with gentle waves reflecting the golden hues of the sunset. The serene horizon is adorned with distant shoreline silhouettes, creating a tranquil waterfront setting.

Apartment in Nahant

Cozy Waterfront Home with Jacuzzi and Fireplace