STAYPINEAPPLE BOSTON | FREQUENTLY ASKED QUESTIONS

If you're arriving by plane from Boston Logan International Airport (BOS):

• Traveling by car: Get on I-90 W, then take S Boston Byp, Frontage Rd and E Berkley St to Chandler St.
• Traveling via public transit: Take the Logan Express Back Bay bus from Terminal E - Arrivals to Stuart St @ Dartmouth St, then walk about 10 minutes to Chandler St. 

Staypineapple Boston does not have onsite parking, but there are plenty of nearby options. We recommend 100 Clarendon Garage, just past the Back Bay Station, a 7-minute walk away. You can also use the SpotHero app to check prices and reserve a spot in the surrounding area.

Staypineapple Boston does not offer shuttle service, but getting around is easy! We’re close to Massachusetts Bay Transportation Authority (MBTA) commuter rail and subway lines, as well as bus routes with nearby stops, plus ride-share options available all day in the area — complete with convenient pick-up and drop-off right at the hotel.

Staypineapple Boston is conveniently located in the South End with easy access to a variety of public transportation options. We are near MBTA stations and stops putting you within quick reach of top attractions like Fenway Park and TD Garden. MBTA also makes it simple to explore neighborhoods beyond the South End like Back Bay and the North End.

Staypineapple Boston offers convenient access to Boston Logan International Airport (BOS), approximately 5 miles west of the South End.

In consideration of all our guests, check-in is after 4:00 PM and check-out is at 12:00 PM. Staypineapple Boston also offers guaranteed early check-in or late check-out for an additional fee. Just let us know in advance, and we'll do our best to accommodate your request based on availability.

We’d be happy to store your luggage at the front desk while you wait for your room to be ready, or after you’ve checked out if you’d like to explore a bit more before departing.

The amenities included in your stay have you covered from check-in to check-out. Start with a complimentary CORE Welcome Drink, then enjoy some Afternoon Delights of pineapple cookies and coffee. Explore the city on our Pineapple Bikes and stay hydrated with our refillable PATH water bottles. End your day in cozy double duvets with our Naked Experience, then wake up refreshed with in-room coffee and tea. Do we even need to mention the high-speed WiFi and all your favorite streaming shows right on your TV? Yes, we've thought of everything so you don't have to.

Staypineapple Boston is more than pet-friendly, we're pet-obsessed! Dogs, cats, pigs — you name it — we roll out the red carpet so your furry (or feathery) travel companion can enjoy the stay too. We also make it easy to save on your pet’s stay with our Pineapple Pup Package! Get 50% off the pet fee plus fun treats and goodies for your cuddly pal.

Let's set the record straight! Staypineapple Boston and every Staypineapple hotel is family-friendly, making every stay comfortable and enjoyable for kids, adults and everyone in between.

We don't have a fitness room, but being in the heart of the South End, you can rack up your steps by exploring charming shops or taking a scenic stroll around Back Bay.

Our in-house bar and restaurant, Trophy Room, located on the first floor of Staypineapple Boston, is a local favorite, serving all-American classics and inventive cocktails in a lively, welcoming atmosphere. Trophy Room is open Monday-Thursday from 4:00 PM to 11:00 PM and on Fridays from 4:00 PM to 1:00 AM. Weekend breakfast is served from 8:00 AM to 12:00 PM, and the restaurant stays open until 1:00 AM on Saturdays and 10:00 PM on Sundays. For the full menu and more information, visit Trophy Room's website.

If those emergency snack cravings hit, don’t worry — you can grab something from our Quick Bites & Bevvies anytime, day or night. 

We’d be happy to accept packages on your behalf. Please call our team at (857) 444-6111 in advance so we know to expect it. Be sure to address your package to:

[Your Name]
c/o Staypineapple Boston
26 Chandler St
Boston, MA 02116

Staypineapple Boston does not offer meeting or event spaces.

Staypineapple customer service is just an email or phone call away at [email protected] or (866) 866-7977. One of our friendly team members will be happy to help make your day a little sweeter!

While we don't have a traditional (and let's be real, boring) loyalty program, we have something 10 times better. The CORE gives members the lowest rates at any Staypineapple hotel, plus instant savings, exclusive offers and special packages that make every stay sweeter. Learn more and join The CORE today!

Whether it’s a wedding, family reunion, business event or any reason to gather, Staypineapple Boston offers group rates that make it easy for everyone to stay together. To book your group, email [email protected] or call (206) 823-3903. For more information, visit our Groups page.

Booking direct with Staypineapple gets you the lowest rates you won't find on the big online travel sites. By skipping the high fees charged to us by “the usual suspects,” we pass those savings straight to you! Even better? When you join The CORE, you'll unlock the lowest rates, exclusive offers and special packages... because who doesn’t love a sweet deal?

At check-in, your debit or credit card will be authorized for your room charges, taxes, and a $50 incidental hold per day of your stay. Room charges and taxes are typically processed at check-out, while any unused incidental hold may remain on your account for up to 21 days depending on your bank. If you choose our Seal the Sweet Deal rate when booking, you can lock in our lowest rates and pay the full room amount and taxes at the time of booking, so you don’t have to worry about it when you arrive.

Massachusetts residents get 20% off their stay when they show a state-issued ID at check-in. Turn your everyday routine into the ultimate staycation! Book now to snag your discount.

Staypineapple Boston is in the heart of the South End, close to top attractions! Take a short 12-minute walk to Boston Common to enjoy scenic walking paths, the Freedom Trail, and the famous Swan Boats. A quick 10-minute walk to Arlington Station lets you hop on the MBTA Green D Line and reach Fenway Park in just 7 minutes. To catch an exciting Celtics or Bruins game at TD Garden, walk 10 minutes to Back Bay Station and take a 12-minute ride on the MBTA Orange Line.