Smoking friendly holiday rentals in Essex County

Spacious 2BR Free Parking king bed family friendly

Very large rooms hardware floors throughout the condo with a king bed and there’s a crib the large bathroom has a shower and tub there’s two arcade games a computer and printer all available in the apartment to use. It can sleep 8 people with the sofa that open up to a bed as well as an air mattress the condo has everything you need as if you were home So bring the whole family to this great place with lots of room for fun4people sleep in beds 1-2 people on a sofa bed and there’s one air mattres

Pristine Private Bedroom Close to Davis Square

Travelers Welcome!! A Renovated 2 bed condo near Davis Square and Tufts, and only 5 minutes from the new Ball Sq Green line MBTA station, supplying amazing access to downtown Boston. Guests have access to a private bedroom with exclusive porch. Beyond the bedroom there's a full kitchen, living area, dining room, bathroom and back sunroom. TV/wifi, back deck, hammocks, free laundry machines and ample parking all at your disposal. I try to offer the best short term rental situation possible.

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.

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.

Private 2BR Suite near Boston w/ Parking & Patio

Enjoy a quiet, private retreat in one of Waltham’s nicest suburban neighborhoods. This clean, stylish suite offers nice bedrooms, modern bathroom, smart TVs, fast WiFi, and a dedicated workspace perfect for relaxing or working remotely. Conveniently located minutes from Bentley University, Brandeis University, Gann Academy, Lasell University, and easy access to Boston/Cambridge. Ideal for visiting families, students, professionals, and extended stays. Free parking and Patio with a grill!

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.

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)

Castle Hill Lookout - Spacious and Cozy Home

Open concept living area with a work space, private third floor balcony with plenty of parking. Just 1 mile from Historic Downtown, the bustle of the city is a refreshing 20-30 minute walk away, catch a ride to get there in less than 5. Nearby: Forest River Park and Salem Willows Park. Beaches in Salem, Swampscott, Marblehead, and Beverly. 30 mins from Logan Airport and 35 minutes from downtown Boston. Easy to take the train into Boston as well.

Premium Private Room Near Boston & Airport 10 Mins

Upgrade your stay with this hotel like Airbnb, serviced 24/7 with staff on property at all times • Free Parking • Full Size Bed • Free Laundry Service ( Washed + Folded ) • Free Coffee at Check-in • Mini Bar, Snacks, bathroom needs ALL available & CHEAPER than local stores by 5% • Towels provided daily • 65” TV • Sound proofed room • Air purifier provided • All streaming services provided • Home Gym • 10 mins to Boston • 3 Mins to I-93

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.

Vintage 2 Bed-Walk to Davis/Train/Tufts- NEW BATH!

Beautifully renovated 2-bedroom condo near Davis Square, Tufts University, and just minutes from the Ball Square Green Line station, with easy access to downtown Boston. This sunny, fully furnished home offers a relaxed, comfortable base with two bedrooms, a brand-new bathroom, modern kitchen, living/dining area, sunrooms, outdoor space, high-speed internet, in-unit laundry, smart TV, and thoughtful touches throughout.

The Gatehouse at Castle Hill

A cozy second floor apartment with a work space, private balcony, and plenty of free on street parking. Just 1 mile from historic downtown, the bustle of the city is a refreshing 20-30 minute walk away. Catch a ride to get there in less than 5. Nearby: Family parks, beaches and restaurants. 30 mins from Logan Airport and 35 minutes from downtown Boston. Easy to take the train.