Holiday rentals with a patio in Chelsea

4.98 out of 5 average rating, 114 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).

4.86 out of 5 average rating, 159 reviews

A wooden table featuring a natural, textured surface holds a decorative bowl and a small green plant. A softly lit lamp and a vase with white flowers are also visible. The wall art depicts two silhouettes of deer amid foliage, adding a serene touch.

Guest suite in Revere

Studio Close to Beach, Boston, Airport & Train

Modern and cozy basement studio just 10 minutes drive from Logan Airport, 5 minutes from Revere Beach, and 14 minutes from Downtown Boston. Fully equipped with a kitchenette, full bathroom, high-speed internet, and a 75-inch Smart TV. Enjoy entertainment options like a foosball table, Xbox, and board games. Step outside to a private lounge area with a fireplace and grill. Free driveway parking and plenty of nearby restaurants make this the perfect home base for comfort, convenience, and fun.

4.95 out of 5 average rating, 153 reviews

A well-lit living area features a cozy white sectional sofa and a stylish floor lamp. Light from large windows illuminates the space, highlighting the warm wooden wall design. A round mirror complements the room, while a small table is adorned with decorative plants.

Apartment in Brighton

The Murthy : Bright • Spotless • W/D

Enjoy Boston in this elegant suite for long and short stays. Just a 5 min walk from the T and close to Boston College/Harvard, you can tastefully engage with all of Boston. Unit Features -> Blazing Fast WiFi -> 65” Roku TV Living Room -> 50” (x2) Roku TV Bedroom -> Fully Stocked Kitchen -> 2 Queen Bed -> 1 Twin Bed -> 1 Sleeper Sofa Rolling cot and air mattress available on request! Ideal for business travelers, couples, nurses, and everyone looking to experience Boston in style!

4.99 out of 5 average rating, 119 reviews

A dining area is presented with a rustic wooden table surrounded by white chairs. Lush green plants are displayed throughout the space, enhancing its natural light. A geometric pendant light hangs above, while large windows provide views of the bright, open living area beyond.

Home in Medford

Bright Family Oasis Near Boston w/ Parking

Bright, plant-filled oasis in a quiet Medford neighborhood just minutes from Boston, with easy access to transit and free parking. Guests return again and again for the spotless cleanliness, curated art, and true “home away from home” feel. Enjoy a fully equipped chef’s kitchen and private backyard. Perfect for exploring the city, then relaxing in a peaceful, beautifully designed space. Or working from home. Conveniently located for day trips to Salem, Cambridge and downtown Boston.

4.95 out of 5 average rating, 109 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.

4.98 out of 5 average rating, 300 reviews

Apartment in Medford

Hipster Basecamp | Fireplace • Views • Parking

Welcome to Hipster Basecamp, a curated space where mid-century design meets modern comfort. Enjoy bold touches like a double-sided fireplace, Smeg appliances, and a ceiling-mounted rain shower. Brew espresso or mix cocktails with everything at your fingertips, then head to the deck to unwind and take in the peaceful view. Admire original artwork throughout — and if a piece speaks to you, it's available for purchase. (*note: record player is currently out of order)

4.95 out of 5 average rating, 153 reviews

A spacious yacht is docked along a wooden pier. The boat features a white exterior with a flybridge and is surrounded by calm waters. In the background, other boats and waterfront buildings can be seen under a clear blue sky with a few fluffy clouds.

Boat in Charlestown

2BR Spacious Yacht - Heat & AC- On Freedom Trail

The coolest way to stay in Boston: not a water view — you're ON the water. Carpe Diem II is a yacht in Charlestown Navy Yard with 2 queen staterooms, each with a private bathroom and shower, for up to 4 adults. Fall asleep to the harbor rocking you, have dinner and cocktails on the aft deck as boats cruise past, and stay comfortable with central A/C and heat. The Freedom Trail, North End, and Downtown are steps away. Hotels have views. You'll have the harbor.

4.89 out of 5 average rating, 114 reviews

A living area is presented with a wall-mounted television and a small wooden table. A light-colored armchair and a decorative plant enhance the space. Dark curtains frame a window, and a patterned rug adds texture to the dark hardwood floor.

Apartment in Revere

Apartment in Revere near the airport

Enjoy the simplicity of this quiet and central accommodation. Located in a strategic area. Close to the airport, beaches, shopping malls, train station, Downtown Boston, etc. The apartment has a bedroom, large kitchen, living-dining room, full bathroom and an outside terrace overlooking the interior of the property. The living-dining room has the peculiarity of having a door with a lock so it can be used as an additional private room if required.

4.96 out of 5 average rating, 200 reviews

The entrance to the suite is adorned with lush greenery, creating a welcoming facade. A door leads into the unit, framed by railings and planters. The area is bordered by stone pathways and garden beds, enhancing the natural appeal of the space.

Guest suite in Chelsea

Modern Suite Near Boston, Airport & Downtown

Enjoy a spacious, private suite with its own entry and free parking on Admiral's Hill. Nestled in a secure, gated community, this peaceful retreat offers stunning city views and direct access to Mary O'Malley State Park. Perfectly located minutes from Logan Airport. Easy access to downtown Boston via public transit, it’s ideal for both relaxation and convenience.

4.94 out of 5 average rating, 170 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.

4.92 out of 5 average rating, 231 reviews

Apartment in Woburn

Romantic Getaway w/private Jacuzzi• Fire Pit•

Escape to a private romantic retreat just minutes from Boston. Relax in your private outdoor jacuzzi, enjoy the fire pit under the stars, and unwind in a cozy space designed for couples. Located in a quiet area just minutes from Boston, restaurants, and shopping — the ideal spot for couples or a peaceful weekend escape.

4.9 out of 5 average rating, 166 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

Welcome to our stunning Airbnb! Our stylish and modern ranch style home is the perfect place for your next vacation or business trip. Located in a quiet and safe neighborhood, our home is perfect for couples, families, or a group of friends. It features 3 bedrooms and bathroom and can comfortably accommodate 6 guests

Popular amenities for Chelsea Holiday Houses with Outdoor Verandahs

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.98 out of 5 average rating, 104 reviews

The bedroom features a queen bed with a white duvet and an orange throw blanket. Two bedside lamps are positioned on either side. A workspace with an ergonomic chair and a mirror is present, along with a window allowing natural light to fill the room.

Apartment in Medford

Cozy modern retreat near Tufts

4.88 out of 5 average rating, 145 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

4.99 out of 5 average rating, 104 reviews

Apartment in Cambridge

Cambridge Luxury Apartment With Free Parking

4.96 out of 5 average rating, 107 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

4.98 out of 5 average rating, 196 reviews

A well-lit bedroom features a spacious bed adorned with decorative pillows. Natural light enters through a window with blinds, offering a view of the outdoors. A bedside lamp casts a gentle glow, while a piece of wall art adds a touch of color to the room.

Apartment in Lynn

Spacious & Luxury House |Overlooking Boston Harbor

4.99 out of 5 average rating, 138 reviews

A modern kitchen with sleek cabinetry and a spacious island features three high-backed bar stools. Stainless steel appliances are visible, along with a contemporary backsplash. Natural light brightens the space through large windows, offering views of the green meadow outside.

Apartment in Brighton

New 3 bedroom, 2 bath unit, meadow view!

4.99 out of 5 average rating, 102 reviews

A three-story green house features a welcoming front porch with steps leading to an entrance. Lush foliage surrounds the exterior, while a paved pathway and garden beds enhance the outdoor space. A decorative lamp post stands along the pathway, contributing to the charming curb appeal.

Apartment in Cambridge

Spacious 2bd/1ba Apt | Free Parking

Apartment in Downtown Salem

The front porch features two comfortable chairs positioned on a wooden deck. Potted plants with blooming flowers are placed on the steps, alongside a white pumpkin and an orange pumpkin, creating a welcoming entrance. A dark door with glass panels is framed by light from an outdoor lamp.

4.97 out of 5 average rating, 193 reviews

Barton: Heart of Salem, Walk Everywhere, Parking!

Holiday House Rentals with a Verandah

4.92 out of 5 average rating, 382 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

4.98 out of 5 average rating, 155 reviews

Home in Roxbury

Boston 5BR Home w/Free Parking & Yard-Sleep 12

4.94 out of 5 average rating, 194 reviews

The exterior of a charming brick house is presented, featuring rounded corners and a dark front door. Large windows allow natural light to enter, while greenery adorns the adjacent wall. The inviting entrance is complemented by stone steps leading to the doorway.

Home in South End

Charming South End Farmhouse - Near Northeastern!

4.85 out of 5 average rating, 126 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

4.98 out of 5 average rating, 131 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

4.96 out of 5 average rating, 164 reviews

The exterior of the home displays a classic three-level structure, adorned with grey siding and multiple windows. A welcoming front porch features two light fixtures and is accented by purple LED lighting along the base. A wooden front door invites entry.

Home in Medford

Modern Smart Home / EVCharge / Boston / Harvard / MBTA

4.93 out of 5 average rating, 112 reviews

A modern open-concept living space features a well-equipped kitchen with stainless steel appliances and a large island with seating for five. A cozy living area displays a sectional couch facing a wall-mounted TV, with large windows allowing natural light to brighten the room.

Home in South Boston

Heart of Southie - Hot Tub + Walk to Top Bars

4.91 out of 5 average rating, 139 reviews

A modern living area features a stylish orange sectional sofa, paired with decorative pillows. To the rear, the kitchen showcases stainless steel appliances, white cabinetry, and a dining space, while a staircase is visible in the background.

Home in Weymouth

Beautiful 3BR Home by the Water - Family Friendly

Holiday condos with a patio

4.89 out of 5 average rating, 166 reviews

A bright living area is highlighted by a circular dining table surrounded by four chairs. A large round mirror above a white fireplace reflects the light. Warm wooden floors contrast with the cream walls, accentuated by subtle decor elements and natural light from nearby windows.

Condo in Boston

Condo in downtown Boston

4.94 out of 5 average rating, 103 reviews

Condo in Swampscott

Ocean View Coastal Retreat | Walk to Beach | Salem

5 out of 5 average rating, 115 reviews

A small workspace features a marble-top table accompanied by a white chair with a fur throw. The green wall displays a variety of framed artwork and a small chalkboard with the word 'Welcome.' A mirror above the table reflects elements of the cozy room.

Condo in Downtown Salem

The Merchant's Carriage House - Downtown Salem

4.95 out of 5 average rating, 129 reviews

A spacious living area is shown, featuring a light-colored sectional sofa, an accent chair, and a wooden coffee table. Natural light filters through large sliding doors, which open to a private deck. A soft area rug lies beneath the furniture, enhancing the cozy atmosphere.

Condo in South Boston

Boston Townhouse - 3BR/2.5BA - Seaport BCEC

4.95 out of 5 average rating, 148 reviews

Condo in Beacon Hill

Charming and Historic Apartment

4.88 out of 5 average rating, 187 reviews

A private roof deck is showcased with white lounge chairs positioned on a wooden surface. The backdrop features expansive views of the Boston skyline, highlighting various city buildings against a clear blue sky.

Condo in South End

Stunning South End 1BR - private roof deck

4.8 out of 5 average rating, 204 reviews

A well-maintained backyard is featured, showcasing artificial turf and manicured hedges along the fence. Pathways of stone lead through the space, while decorative string lights are hung overhead, adding an inviting touch to the outdoor area.

Condo in Lynn

One bedroom apartment near Boston and Salem.