House holiday rentals in Winthrop

A light blue, single-story home is depicted, featuring a neat front walkway bordered by well-maintained flowerbeds. The entrance includes a solid black door and several windows that allow natural light to fill the space. A manicured lawn complements the inviting exterior.

4.93 out of 5 average rating, 146 reviews

Brand New 3Bed2bath Home Near Logan, Boston &Salem

Welcome to your home away from home! Enjoy a comfortable, stylish, and stress-free stay in this brand-new 3-bedroom home, perfectly located just minutes from Boston’s most popular destinations. Whether you’re traveling with family, visiting for work, or planning a getaway, this space is designed to make you feel relaxed, welcomed, and truly at home. You’ll be just 15 minutes from Logan Airport, Downtown Boston, Salem, Revere Beach, and major highways, with the convenience of free on-site parking

4.98 out of 5 average rating, 153 reviews

An outdoor deck features two ornate chairs and a small table, overlooking a serene sunset. The horizon displays soft hues of orange and blue, with the silhouette of rooftops adding depth to the scene. Lush greenery can be observed nearby.

Home in Somerville

The Nest | A peaceful retreat in the city

Unwind and relax on a quiet street in the heart of Somerville. With easy access to Harvard, MIT, Tufts, and Boston, this newly updated Victorian home is a perfect base to explore all that New England has to offer. You can also visit an abundance of local restaurants and coffeeshops within walking distance. During your stay, you will enjoy full use of a smart TV, comfortable work-from-home setup, brand new washer/dryer/dishwasher/range, off-street parking, and multizone heating/ cooling systems.

4.97 out of 5 average rating, 135 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

Gorgeous Retreat - Amazing Kitchen - Hosts 6

PEACE IN THE CITY - Humble Luxury minutes from Boston, Beach & Casino Whether you travel for outdoor adventure, beach time, family bonding or just hanging out, this gorgeous two-bedroom home – just minutes away from the beach and Encore Casino and less than 20 minutes from the city center – was lovingly renovated and outfitted to curate an experience of being at home, at peace, and surrounded with quiet beauty. Restaurants, Grocery Store, Pharmacy and other conveniences within minutes walk.

4.78 out of 5 average rating, 224 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.

4.92 out of 5 average rating, 319 reviews

A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.

Home in Stoneham

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

4.87 out of 5 average rating, 247 reviews

A modern living area features a light-colored sectional sofa and two patterned chairs arranged around a small table. A wall-mounted television is positioned above a sleek fireplace, surrounded by built-in shelving displaying decorative items. Natural light filters through sheer curtains.

Home in East Boston

Tribeca chic | 2 BR w/private patio

Welcome to our cozy, beautiful, newly renovated home! The house includes free wifi, washer/dryer, recently renovated kitchen along with a dedicated patio. A 2-minute walk to Shaws grocery store & shopping plaza (Marshalls, etc.). A 10-minute walk to the MBTA (silver/blue line). 4-minute drive to Logan Airport. Top-rated restaurants, waterfront, city views, & easy access to downtown Boston. Please note that hosts occupy the bottom floor and are available 24/7 for whatever you may need!

4.85 out of 5 average rating, 102 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.

4.94 out of 5 average rating, 306 reviews

A spacious bedroom is illuminated by natural light from large windows, featuring a comfortable bed with soft linens. Two plush armchairs are positioned across from a cozy sofa. A modern glass coffee table holds a magazine, while decorative elements add charm to the setting.

Home in Cambridge

Stunning urban hideaway nearby Harvard Square

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

4.93 out of 5 average rating, 181 reviews

The kitchen features navy blue cabinetry and modern stainless steel appliances, including a microwave and oven. A white countertop contrasts with the dark cabinets, enhancing the space's elegance. Natural light flows in through the windows, creating a bright atmosphere, while a small rug adds a decorative touch.

Home in Malden

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free

Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. ✔Queen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances ✔Ideal for Families and Staycations ✔Inviting Dinning and Large Kitchen ✔Fast WIFI+Netflix ✔Off-Street Parking ✔Self check-ins with secure keypad ✔Laundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

4.91 out of 5 average rating, 289 reviews

A cozy living area features a beige sofa, a green armchair, and a wooden coffee table with decorative centerpieces. A stylish rug adds texture to the floor. Walls are adorned with artwork and decorative pieces, while natural light filters through the windows.

Home in Lynn

Clean, spacious In-Law Suite -Near Everything

Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.

The living area features a glass dining table surrounded by wooden chairs. A comfortable gray sofa is positioned nearby, complemented by decorative cushions. Natural light floods in through multiple large windows, enhancing the airy and bright ambiance of the space.

4.94 out of 5 average rating, 159 reviews

Modern 2-bedroom w/parking near Encore and Logan

Modern two bedroom with free parking, conveniently located 7 minutes from Boston Logan Airport, 5 minutes from Revere Beach and only 12 minutes to Encore Casino and downtown Boston. No parties or events are allowed in the unit. Penalties apply. DISCLAIMER: For your safety and the safety of others, surveillance cameras are installed outdoors at this property.

4.89 out of 5 average rating, 122 reviews

The dining area features a wooden table with built-in seating, adorned with decorative pillows. A vibrant mural of 'Salem Massachusetts' frames the black accent wall, while natural light enters through a window covered by dark curtains.

Home in Salem

*New Spooky Salem 2BR|Halloween+Downtown|Witches

⛄ Your Salem winter adventure starts here! Cozy 2-bedroom unit just steps from museums, downtown sights, and seasonal events—plus parking is included. ❄️ 🎃 Downtown Salem -5 Min walk ⭐ Salem Commons -4 Min walk 🧙🏻‍♀️ Witch Museum -8 Min walk ✨ Collins Cove Beach -1 Min walk 🕸 Hocus Pocus House -5 Min drive

Popular amenities for Winthrop house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 reviews

A welcoming living area features a large yellow sectional sofa, paired with woven chairs. A colorful area rug anchors the space, complemented by a light wood floor. The walls are adorned with a tropical mural, and a kitchen area is visible in the background.

Home in Hull

NEW! Walk To Beach! Sunshine House

5 out of 5 average rating, 32 reviews

Home in Newton

Elegant & Spacious~Easy Boston Access! STR-25-22

Home in Lakeside Marblehead

A cozy living area is highlighted by a light grey sofa adorned with soft pillows in neutral tones. A round, woven coffee table sits at the center, accompanied by decorative accents. Two lamps provide soft lighting, complemented by exposed wooden beams overhead.

4.93 out of 5 average rating, 41 reviews

Pet-friendly 4-Bed Home w/Pool, Nature Trails

5 out of 5 average rating, 15 reviews

Home in Bedford

Bauhaus Retreat in Nature Preserve w/ Pool

The bright kitchen features white cabinetry and a large island with a marble countertop. Stainless steel appliances, including a refrigerator and a stove, are visible. Natural light filters through multiple windows, enhancing the spacious feel. A dining area with dark chairs complements the design.

4.81 out of 5 average rating, 57 reviews

Boston 15 min away.

4.94 out of 5 average rating, 48 reviews

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

Beautiful Spacious 4BRM House!

4.97 out of 5 average rating, 64 reviews

An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.

Home in Norwood

the house of id; vintage shop, accessible space

4.97 out of 5 average rating, 108 reviews

Home in Weston

Spacious vacation unit in premium suburban town

Weekly house rentals

5 out of 5 average rating, 239 reviews

A charming house is nestled among trees, featuring a light-colored exterior with dark accents. An American flag is displayed outside. The front yard is landscaped with a stone wall and greenery, creating a serene setting. A gravel path leads to the entrance.

Home in Dedham

The Gatehouse, Cheerful 3 bedroom 3 bathroom house

4.93 out of 5 average rating, 107 reviews

A light-filled dining area features a round white table surrounded by six white chairs. A modern light fixture hangs above the table, and a large mirror reflects the space. Natural light streams through the two windows, illuminating a decorative rug on the polished wooden floor.

Home in Jamaica Plain

Beaut private close univ+hospital

4.96 out of 5 average rating, 176 reviews

A dining area is showcased with a rustic wooden table surrounded by four chairs and a bench. An arrangement of circular placemats lies on the table. Natural light enters through a window, illuminating the wooden floor and a potted plant sits on the table.

Home in Salem

Beautiful very spacious historical house in Salem

4.98 out of 5 average rating, 112 reviews

A large tree with a broad canopy dominates the lush backyard, surrounded by greenery. The area features a stone border outlining a patch of grass, with glimpses of the landscape beyond, including wooded areas and a play structure in the distance.

Home in Danvers

Large, Comfortable & Conveniently located Home

4.82 out of 5 average rating, 110 reviews

A comfortable living area is presented with a decorative tree adorned with lights. A faux fireplace sits beneath a flat-screen TV, complemented by a stylish coffee table. Light-colored furnishings and hardwood flooring enhance the inviting design, while a patterned area rug adds warmth.

Home in Wakefield

Beautiful home next to train to Boston, near Salem

5 out of 5 average rating, 18 reviews

A spacious living area is designed with large windows providing expansive views of the ocean. A comfortable white sofa faces a wooden coffee table, complemented by a cozy throw. Natural light fills the room, accentuating the warm wooden floors and tasteful decor.

Home in Nahant

Sea Forever - Oceanfront Home in Nahant!

4.89 out of 5 average rating, 80 reviews

A well-furnished living area features a light-colored sofa adorned with patterned cushions, complemented by a blue ottoman. A large area rug in soft tones enhances the warmth of the hardwood floor. Natural light enters through multiple windows, while a decorative chandelier hangs from the ceiling.

Home in Winthrop

Cozy & Modern Entire Residential Home ❤️

4.83 out of 5 average rating, 47 reviews

A spacious living room features two comfortable sofas adorned with bright floral cushions, complemented by a light throw blanket. A wooden coffee table sits centrally, and large windows allow natural light to fill the area. Decorative accents include a wall clock and a floral vase.

Home in Winthrop

3 bdr, steps from the ocean, minutes from Boston

Private house rentals

4.95 out of 5 average rating, 83 reviews

The modern two-story home features a blue exterior with white trim and three windows on the ground level, complemented by decorative planters. A bold red front door is centrally positioned, enhancing the welcoming entrance.

Home in Charlestown

Spacious & Pet-Friendly Modern Home in Charlestown

Superhost

The sleeping area features a queen bed dressed in a patterned comforter, flanked by bedside tables. A large dresser and a chair are positioned nearby, with natural light filtering through the window. Decorative artwork is displayed on the wall above the bed.

Home in Winter Hill

4.67 out of 5 average rating, 456 reviews

Beautiful Private Lg Space/ Clean Comfy

4.97 out of 5 average rating, 32 reviews

A spacious living area features a large, rounded red leather sofa surrounding a glass coffee table, complemented by a decorative area rug. Light-colored walls and recessed lighting enhance the bright atmosphere. Behind, a dining area with elegant chairs and cabinets is visible.

Home in Stoneham

The Grand Residence

5 out of 5 average rating, 40 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

The living room showcases a plush leather sofa facing a coffee table adorned with a plant and various magazines. The light walls are complemented by the natural wood elements of the staircase. A dining area is visible in the background, featuring a table with seating.

5 out of 5 average rating, 23 reviews

Entire House Near Boston-Salem - Walk to the beach

4.99 out of 5 average rating, 82 reviews

The bedroom features a wooden bed with a light-colored blanket. A small bedside lamp emits soft light next to the bed, while a tall black dresser stands against the opposite wall. Natural light brightens the space through a nearby window.

Home in Cambridgeport

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

4.99 out of 5 average rating, 98 reviews

A collage of a modern kitchen with stainless steel appliances, an outdoor patio with a propane fire pit and seating, a cozy living room featuring a sofa and television, and a basement area with a poker table and arcade game, all designed for comfort and entertainment.

Home in Prospect Hill

Huge NEW Home Boston Harvard MIT Covered Parking