Family-friendly holiday rentals in Chelsea

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

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).

#7 Spacious Modern Home Near Boston w/ Parking

Discover comfort & convenience minutes from Boston, Cambridge, & Salem. Whether you're here for work, family, or fun, this stylish 2-story home has everything you need for a relaxing & memorable stay, plus we are experienced Superhosts! 🛏 3 Comfy Bedrooms + 1.5 Baths 🍳 Fully Equipped Kitchen 📶 High-Speed Wi-Fi + Smart TVs 🚗 Private Parking for 2 Cars 🧺 In-Unit Laundry 🔥 Backyard BBQ + Fire Pit + Outdoor Seating for 4 🌆 Easy Access to Local Attractions 🏡 Perfect for families 5⭐ Reviews

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.

10 min Logan Airport- 3Bed/ 2Bath, Sleep 7

Welcome to my charming townhouse in the heart of Chelsea. An ideal retreat for your stay near Boston. Conveniently located just a few miles away from all the Bostons attractions, my townhouse offers easy access to the best that Boston has to offer. Whether you're here for business or pleasure, you'll find everything you need for a memorable stay right at your fingertips. Book your stay at my townhouse today and experience the perfect blend of comfort and convenience for your Boston trip!

Cozy Winter Cabin Near BOS, Airport w/Parking

Private and spacious lower level 550 sq ft studio close to the city. You'll be a quick 10-20 mins drive to downtown Boston, and 30-40 mins to coastal towns, including Salem. You'll have a reserved driveway parking spot on a quiet residential street. We provide guests with a professionally cleaned cabin, plenty of towels, and coziness! We are located on a quaint and low-traffic hill, so if you are walking to the bus, it is 0.7 mi away, with inclines. Access to our home requires steps

Cozy studio, near beaches and city skyline views

The Boston Skyline sunsets are beautiful during the summer, just a minute down the street from your Airbnb. This cozy studio, with private entrance, and bathroom includes FREE off-street parking, high-speed internet access, comfy and cozy queen bed with premium linens, nespresso, fridge, with complimentary munchies and NO cleaning fee. Check out the beaches and restaurants. Relax watching your favorite show on the HD smart television or catch up on work with the spacious desk area.

Luxury Grand Oasis | Pool · Gym · Parking · 2BR

Discover your exclusive retreat in Everett. Immerse yourself in sleek, curated living with designer finishes and resort‑style amenities for an unforgettable stay. Highlights: • Steps from downtown Boston via easy Silver Line & Route 1 access • Sparkling pool with cabana seating and courtyard fire pits • 24/7 state‑of‑the‑art fitness center & dedicated yoga studio • Private music room, co‑working pods & on‑site community pet spa

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.

The Chelsea House- Minutes to Downtown-Charming.

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.

Modern studio, FREE parking, close to LoganAirport

Bright & cozy studio. Ideal for one or two people looking for the perfect space to stay near LOGAN AIRPORT, Revere Beach, Encore Casino and Downtown-Boston. It has everything you need for your Boston trip. One full sized bed, private bathroom, kitchen with a dining/living area, TV, WIFI, coffee machine and FREE Parking.