
Family-friendly vacation rentals in Chelsea
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Chelsea

Total vacation rentals
Explore 110 vacation rentals in Chelsea

Nightly prices starting at
Chelsea vacation rentals start at G$14,644 GYD per night before taxes and fees

Verified guest reviews
Over 9,740 verified reviews to help you choose

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
110 of Chelsea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chelsea rentals

4.8 Average rating
Chelsea stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Chelsea
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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.

Stunning Oceanview-4 Train Stop Logan Airport
Stunning 1 bedroom huge apartment with partial ocean views of Revere Beach. This upscale home has it all!! Just one flight up then you enter a hardwood floor foyer, opens to a huge living room with upscale decor, large eat in kitchen stainless steel appliance, country table has seating for 4, tile floor, gas range, and lots of cabinet space, with views of Revere Beach and ocean, giant bathroom complete with tiled shower and stackable laundry (Washer and Dryer) and huge bedroom with closet.

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.

#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

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)

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.

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.

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.

Private Luxury Retreat | Pool · Gym · Parking
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.

Comfort apartment 3bed/2bath near Boston
Recently renovated apartment with new supplies, sheets, and 3 new mattresses!! My apartment is located near Boston in a very quiet, safe, and peaceful neighborhood. Great Location! 15 minutes from the Airport! 10 minutes away from the new Casino!! 15 minutes away from Downtown Boston! Very Close to Whidden Hospital in case of an emergency. NO PARTIES ALLOWED.
Popular amenities for Chelsea family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Stay in Somerville | River & City View

Romantic Getaway w/private Jacuzzi• Fire Pit•

BC/BU - Beautifully Renovated Penthouse 3-BR/2-BA

Wellesley Spacious and Modern

Oceanfront Pool. Close to Boston. Free Parking.

Headers’ Haven

Lakeside apartment, patio, hot tub, outside shower

Waterfront w/private beach, hot tub, & firepit!
Family- and pet-friendly home rentals

Licensed Boston airport studio 5 stars, subway

Spacious 3 Bedroom Apartment with King Bed

2-Bedroom Ocean View Walk to Beach and Downtown

Cozy, historic 3 bedroom home close to Boston!

Ocean view studio with hot tub & access to Boston

Private apartment near Boston/Airport/Beach/Train

The Day-Burrill-Wadsworth-La Voix House

Private Studio w/ Loft Center Historic Carlisle
Family-friendly home rentals with a pool

Cozy 1BR Near Boston w/ Pool & Gym

the house of id; vintage shop, accessible space

Theatre | Arcade | Pool w. Free 3 Car Parking

Spacious vacation unit in premium suburban town

Private Pool Retreat w/Fire Pit Near Singing Beach

Cozy Private Suite halfway between Cape & Boston

Country Cottage in the City

Cozy Private Studio Unit w/ Laundry and Parking!
When is the best time to visit Chelsea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,379 GYD | G$29,915 GYD | G$31,589 GYD | G$40,584 GYD | G$44,140 GYD | G$51,881 GYD | G$43,094 GYD | G$42,885 GYD | G$43,931 GYD | G$45,395 GYD | G$38,910 GYD | G$35,772 GYD |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Providence Vacation rentals
- Bar Harbor Vacation rentals
- Salem Vacation rentals
- Fenway Park
- Harvard University
- Hampton Beach
- TD Garden
- Gillette Stadium
- Boston Common
- Boston Seaport
- Revere Beach
- Boston University
- Boston Convention and Exhibition Center
- Freedom Trail
- New England Aquarium
- Onset Beach
- Canobie Lake Park
- MIT Museum
- Duxbury Beach
- Northeastern University
- North Hampton Beach
- Crane Beach
- Quincy Market
- Tufts University
- Harvard Square
- Roger Williams Park Zoo
- Prudential Center





