Apartment holiday rentals in Winthrop

4.99 out of 5 average rating, 168 reviews

An inviting open-concept living area features a brown sectional sofa with a chaise, accented by throw pillows. A round coffee table sits in front, surrounded by a welcoming atmosphere of honeybee-themed decor, such as hexagon shelves on the wall. A workspace with a chair is positioned nearby.

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.

4.74 out of 5 average rating, 133 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.

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, 264 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.

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, 242 reviews

Quiet Neighborhood Luxury Stay

The apartment is brand new with a modern feel to it. Available with all the amenities needed for your convenience. Very quiet, clean, and safe neighborhood. Close to everything you desire, 1 minute to the beach, 8 minutes away from the train station, 1 minute away from the T-Bus stop, 9 minutes to Logan Airport, 12 minutes to Downtown Boston, 15 minutes away from Encore Casino, food and coffee shops, such as Starbucks and Dunkin' Donuts in the area. Perfect for a family stay or a business trip.

4.94 out of 5 average rating, 156 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.

4.95 out of 5 average rating, 209 reviews

A spacious living area is presented with a comfortable sofa and an elegant armchair. A dark coffee table sits at the center, while a dining table is visible in the background. Natural light illuminates the room through the windows, enhancing the cozy atmosphere.

Apartment in Woburn

Comfy-Spacious-private 1BR conveniently located

This stylish, private place is perfect for a couple or a small family. Conveniently located minutes from Boston or the north shore whether you are traveling by car, Uber, or local train. Enjoy Boston adventures, north shore excursions, beaches, fall leaf peeping, skiing, historical visits to Massachusetts battle grounds, or some retail therapy at shops and malls nearby. An array of local and city restaurants and breweries provide a multitude of options for your pleasure. YMCA just steps away!

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, 148 reviews

Spacious 3 Bedroom Apartment with King Bed

Family friendly, walk-out basement style apartment close to everything! Clean and safe neighborhood. A 10 minute walk to two beaches: Revere Beach - America's first public beach & Short Beach - a neighborhood favorite. 5 minute walk to Beachmont T station and bus lines - 15 minutes to Downtown Boston! 10 minute drive to Logan or 20 minute drive to the Casino. 25 minute drive to Salem. Walkable to an Italian Bakery, Dunkin Donuts and Starbucks as well as a number of restaurants and eateries.

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, 164 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.

4.88 out of 5 average rating, 223 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.

The exterior of a two-story blue house is presented, featuring a brick facade and multiple windows. A covered porch with stairs leads to the entrance, surrounded by neatly trimmed shrubs. Sunlight illuminates the scene, highlighting the clear blue sky.

4.75 out of 5 average rating, 194 reviews

The Price is Right Boston Airport Beach Park Free

Private spacious 1 bedroom 1 bath attic apartment with new rug/paint/ac. Nice little skyline view of Boston in a beautiful safe quiet residential neighborhood. Great place to rest your head or use as a base to Boston The Encore Casino Salem & beyond! Bedroom comfy mattress/sheets 55” Smart TV blackout shade ceiling fan nightstands lamps 2 chairs Living Areas sofa bed 55” Smart TV sitting chair table 2 chairs/lamps Kitchenette fridge microwave Keurig toaster oven dishes silverware glass

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, 122 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.

4.99 out of 5 average rating, 150 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.

Popular amenities for Winthrop apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.98 out of 5 average rating, 420 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

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, 86 reviews

Pleasant Place 2

Apartment in Prospect Hill

A modern living area features a spacious sectional sofa draped with a decorative blanket. The open kitchen is visible in the background, equipped with sleek appliances and bar seating. Natural light enters through multiple windows, highlighting the neutral color palette and cozy atmosphere.

4.97 out of 5 average rating, 108 reviews

Modern 2 Bed Near Boston

4.86 out of 5 average rating, 105 reviews

A cozy living room features a wooden accent wall with a mounted television and a modern electric fireplace beneath it. Two teal chairs are arranged beside a wooden coffee table, while large windows with black and white striped shades are framed by light curtains, allowing natural light to enter the space.

Apartment in Revere

Chic/Cozy2BR-nearAirport & Beach

4.92 out of 5 average rating, 103 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

4.87 out of 5 average rating, 133 reviews

A private wrap-around porch is shown, featuring a wooden dining table with matching chairs. Sunlight filters through, illuminating the surrounding neighborhood with cozy homes and greenery visible in the background. The space is complemented by a decorative plant on the table.

Apartment in Swampscott

Ocean views, Large Deck, Grill, Kid/Dog Friendly

Apartment in Coolidge Corner

4.98 out of 5 average rating, 151 reviews

New Luxury 2B2B Apartment, One Free Parking

4.89 out of 5 average rating, 118 reviews

A bright bedroom features a spacious bed with soft linens. Nightstands with lamps are positioned on either side. Large windows allow natural light to fill the room, which is adorned with neutral-toned walls and a simple wall art piece above the bed.

Apartment in Malden

Luxe Serene 1BR 15 min from Boston with Gym & More

Private apartment rentals

4.88 out of 5 average rating, 111 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

4.94 out of 5 average rating, 160 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

Apartment in East Cambridge

A bright bedroom features a spacious bed with a patterned blue and white coverlet. Natural light enters through two windows, complemented by circular and square artwork above the headboard. A small table lamp and a side table add functionality to the inviting space.

4.97 out of 5 average rating, 274 reviews

Sunny & Spacious w/FREE parking near Kendall/MIT

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

4.96 out of 5 average rating, 135 reviews

An open living and dining area is highlighted by a wooden dining table set with decorative plates. The space features grey upholstered chairs and a cozy seating arrangement with light-toned furniture. A circular chandelier hangs above, while exposed brick accents add texture to the room.

Apartment in Ashmont

🎖The Ashmont Suite | Close to Subway + Downtown🎖

4.84 out of 5 average rating, 512 reviews

A modern kitchen is presented with dark wood cabinets and granite countertops. Stainless steel appliances, including a refrigerator and oven, are featured. The space is well-lit with natural light coming through a nearby window, complemented by a mosaic tile backsplash.

Apartment in Revere

-1 Sophisticated 3 BR/2 Bath/Prkng By Airpt/Boston

4.97 out of 5 average rating, 220 reviews

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.

Apartment in Salem

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

4.97 out of 5 average rating, 126 reviews

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.

Apartment in Salem

The 1870 Langmaid House Suite

Apartment rentals with a hot tub

4.93 out of 5 average rating, 178 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

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, 26 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, 3 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

Charming Beach Home with Jacuzzi and Fireplace

4.8 out of 5 average rating, 142 reviews

An office space features a black ergonomic chair positioned at a desk. Green carpeting complements a decorative plant placed near the window. In another image, a wooden hot tub is surrounded by plants, with steps leading up to its edge. A cozy bedroom shows a large bed dressed in teal linens, with artwork and a clock adorning the wall.

Apartment in Cambridge

Studio Apt private bath+ Hot Tub, free parking