Family-friendly holiday rentals in Chelsea

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).

Luxury Boston Home +Free Parking +5 mins to Casino

The Cottage 1925 is the epitome of a fun filled getaway. Offering a wine fridge in the main room, 90 inch waterfall peninsula, 70 inch TV, central air and off street parking. Spend the day shopping at Assembly row mall or game night with friends at Lucky Strike. Have a night out at a 5 star restaurant or try your luck at Encore Boston Casino. Make sure to visit “Little Italy,'' famous for its Italian food and feasts or catch a Celtics game at the Garden. The Cottage1925, home away from home.

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.

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.

10 min Logan Airport- 2 Bed/2 Bath, Sleep 5

Welcome to our 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, our 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 our townhouse today and experience the perfect blend of comfort and convenience for your Boston trip!

-2 Traditional 3 BR/2 Bath/Prkng By Arprt/Bos

Our 2nd floor condo is close to the airport and was gutted and totally rebuilt with high-end finishes. There is plenty of space for guests in your group to sit, relax, and mingle. There is a kitchen. a formal dining room, a master BR with en suite bathroom, 2 more BRs and a 2nd bath. Please specify the number of guests in your group when booking. Access and rate depend on the number of guests. See our other listings https://www.airbnb.com/h/reveregem1 https://www.airbnb.com/h/reveregem

Near Boston / Everett historic two-bedroom

Cozy 2-bedroom apartment in charming historic 1920's home with original bathroom and original woodwork throughout, updated with modern amenities. Enjoy an amazing night's sleep on new luxury mattresses topped with crisp hotel-style linens, dreamy pillows, and cozy comforters. Cook dinner in the fully-stocked kitchen. A short Uber or subway ride into Boston. Close to Encore Casino, Assembly Row; and centrally located for day trips to Salem, the ocean, or the lakes and mountains of NH.

10 minutes to Airport-Boston-Casino (2G)

(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.

Spacious 1BR Near Revere Beach | Quick Boston Trip

👋 Welcome to your chic 1BR retreat near Revere Beach with easy access to Boston! This modern basement unit features a private entrance, queen bedroom with blackout curtains, fast WiFi, dedicated workspace, Smart TV, and full kitchen. Relax in the shared backyard or explore nearby parks, trails, and waterfront spots. Ideal for remote workers, couples, weekend travelers, or business stays near Boston and Logan Airport.✨

5 minutes to downtown. Charming. Clean. Cozy.

THE CHELSEA HOUSE: A well-maintained 1900s apartment located on the third floor of a quiet, clean three-family brick building on a small one-way street. It features hardwood floors, exposed brick, and slanted loft ceilings creating a charming, warm, and cozy atmosphere. Parking is included. The Chelsea House is our home away from home, and we have decided to share it with others. Thank you in advance!

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.