Family-friendly holiday rentals in Chelsea

Huge 1BR w/King Bed near Airport, Boston, Salem

Location: Quick 10-20 mins to the center of Boston, 25 mins to Salem. Easy access via multiple major highways, or walk 0.7mi (HILL) to bus, taking you directly into the city. This unit is an upper-level apartment of our home (i.e., STAIRS). Enjoy self-check-in and a reserved parking spot. Living room: Roku enabled TV. Mini-kitchen: Two burner stovetop, microwave, a 4 cu. sqft fridge, and a Keurig. Bedroom: king-sized bed with down alternative pillows and tempur-pedic memory foam topper.

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.

#9 Modern Home 15 min to Boston w/ Yard & Parking

Stay in this stylish 2-story home 3 Comfy Bedrooms + 1.5 Baths! Ideal for families or groups, it comfortably fits 6+ guests. Enjoy a fully stocked kitchen, dedicated workspace, and a private backyard with a gas BBQ & fire pit. Perfectly located for exploring Boston, Cambridge, and Salem with free private parking. Your memorable stay with experienced Superhosts awaits! 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🌆 Easy Access to Local Attractions

Corner Cottage - cozy studio just north of Boston

Whether you’re a tourist visiting Boston for the weekend, a traveling nurse in search of a medium-term stay, or a pilot/flight attendant needing overnight accommodations, this completely renovated and professionally cleaned AirBnB is perfect for you! Finding living accommodations is tough; finding a reliable and responsive host is even tougher. Not only is this unit well equipped with almost everything you may need, but I will do my best to ensure your stay is the most comfortable.

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.

Hipster Basecamp | Deck • Design • 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)

Winthrop Hideaway | Near Airport, Beaches & Boston

Escape to Get to the Point Boston, a cozy private studio in charming Winthrop just minutes from Logan Airport and downtown Boston. Enjoy free off-street parking, high-speed WiFi, premium linens, a Nespresso coffee station, complimentary snacks, and no cleaning fee. Walk to beaches, parks, restaurants, and stunning Boston skyline sunsets. Perfect for couples, business travelers, airline crews, and weekend explorers seeking comfort, convenience, and value.

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.

Curated Designer Retreat • Pool • Gym • Dining

Experience modern Everett living in this bright 2BR/2BA home! Enjoy a fully equipped kitchen with stainless steel appliances, in-unit laundry, and spacious sunlit living areas. Relax by the courtyard pool, stay active in the 24/7 fitness center, or unwind in the outdoor lounges and fire pits. Close to Encore, Assembly Row and major highways for easy access to Greater Boston.

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.

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.

Convenient Cozy Clean Public Trans Free parking

THE CHELSEA HOUSE: A charming 1900s third-floor (24 steps) apartment in a quiet, clean three-family brick building on a one-way street. Features include hardwood floors, exposed brick, and sloped loft-style ceilings that create a warm, cozy feel. Parking included. This is our home away from home, and we’re happy to share it with you. Thank you for staying.