Smoking-friendly holiday rentals in Boston

The Prattville Pad, close to all your needs!

This home is situated across the street from a beautiful community park, which has basketball courts and a baseball field. The area is also great for a neighborhood walk with beautiful Boston views within just 10 minutes. There’s a bus line with easy access to Boston on the street corner, It's also conveniently located minutes from route 16 and route 1. There are 3 fully stocked convenient stores within walking distance as well as a supermarket near by and plenty of restaurants to order from.

Lovely sunny 2 BD home, great area. Free Parking

Beautiful sunny 2 bedroom, bottom unit in 2 family house. A wonderful residential neighborhood just a few houses away from JFK birthplace. Nice tree-lined side street but close to all amenities, shopping etc. There are restaurants, stores and conveniences nearby. Fully equipped and beautifully appointed. A/C units in every room during summer. Parking onsite included. Great location close to public transportation and Boston University, Longwood med center and Fenway and parks nearby.

Charming 2BR Condo, Walk to Downtown Salem

Enjoy this newly renovated, cozy, two-bedroom condo right on the edge of downtown Salem! Beautiful open concept with a great living room area for TV & nice kitchen with all the amenities you could need. 2 bedrooms with one doubling as a home-office (incl. monitor.) Central AC/heat and room for two parking spots in back driveway (a rare-find in Salem!) A 6 minute walk gets you to the train into Boston, 10-15 minute walk to restaurants, bars, and all the historic features Salem has to offer.

Charming 2Bed • Super Clean • Nature & City Life

Charming, super-clean 2-bed in a walk-out lower level, surrounded by nature in the city. Enjoy the best of both worlds in this cozy, spotless space beside 10+ acres of forest — a true retreat in an urban setting. Includes everything shown in the photos: combined living, dining, and kitchen area, full bathroom, and two comfortable bedrooms. Only neighbor is the unit above, so expect some noise. Walk to Horn Pond for waterfront strolls or hikes. Great food and shops in Woburn and Winchester.

Charming 1Bd Apt. in Historic Arlington Home

This lovely apartment is part of our charming and historic New England home. Guests have their own private entrance and an entire 1bd/1.5ba apartment to enjoy. Our quiet neighborhood has access to public transportation and is close to Boston, Cambridge, Somerville and Medford. It is the perfect spot if you are in town on vacation, for work, or for an event! We are happy to help with anything you might need but will otherwise give you your privacy. We look forward to your stay in Arlington!

Charming Dedham Retreat !

Welcome to your stylish 2 floor 2-bdr oasis in the heart of Dedham! This modern, equip apartment is perfect for convenience lovers—just minutes from Legacy Place, with its shopping, dining, and entertainment, plus CVS and fast-food favorites right around the corner. You’ll enjoy easy access to the highway, making commuting a breeze. Relax in a comfortable, elegant space that puts the best of Dedham right at your doorstep! 20 min Drive from Gillet Stadium where the World Cup will be hosted.

Charming Studio Apt! | Back Bay

This special place is close to everything, located between two of Boston's best neighborhoods, the South End known for its food scene and the Back Bay home to great shopping and coffee bars. This studio is on the 2nd Level of an old Boston brownstone. It is equipped with a full private bathroom, fridge, oven, cabinets and closet, all packed into approximately 228 sqft. Its history dates back to the early 1900s where it was originally run as a Lodging House for short term stays.

Salem Waterfront Couples Retreat - 1 mi Downtown!

Welcome to the most amazing place to stay in Salem! Enter through your private entrance to access your 12' ceiling lofted suite featuring a King bedroom that opens up to your own private living & kitchen area with a massive glass wall with ocean views! Your private suite features a beautiful master suite with custom tiled shower & washer/dryer. Living area is open concept with custom designed chef’s kitchen, additional bathroom, huge island, espresso bar, 50’ private balcony.

4br SouthBoston free parkg nrBeach, 6 min>BCEC

Bring the whole family or team -- you'll love our quiet, safe, beachside neighborhood. Our location on the South Boston peninsula means more peace and less traffic, yet a short scenic walk up K Street brings you to great restaurants. <5min walk to a great grocery store, the legendary L St Tavern and L St Bathhouse. <1.5 mi to Convention Center & Seaport. 3 BRs w queen beds and 1 sm BR w bunks, large kitchen, liv & dining rooms, & bonus sunroom w/desk. Call us today -- we'd

Hipster Basecamp | Modern • Roofdeck • 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)

2-bedroom rental unit w/ free parking in driveway

Enjoy a stylish experience at this centrally located place in Downtown Melrose, MA. Newly renovated 2-bedroom apartment, with parking in a multifamily building with quaint front/back patio space to enjoy the fresh air and chat with friends and neighbors. There is 2 car parking available for guests and a city parking lot next to building for additional spaces if renting a car. Master room is large with closet space, and queen size bed.

Spacious 4BR Apartment – 2ND Floor

4 Bedroom, 1 Full Bath Apt – 2ND FL Ideal location near public transportation 2 min walk to Sutherland Green Line Station 5 min drive to Boston College, shops, and restaurants WiFi Free laundry Fully equipped kitchen (4 mini fridges – one per room) AC in all rooms *ALL GUESTS MUST BE REGISTERED IN THE RESERVATION Weekend parking available – $30/night Paper cups/dishes *Key codes sent around 1pm on check-in day