Smoking friendly holiday rentals in Massachusetts

Luxury w sunny balcony in best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

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.

the Elevated Escape

Indulge in a luxury one bedroom guest house... lovingly curated as a complete retreat from the outside world, located in the oldest town on Cape Cod. The Elevated Escape is loaded with charm and drenched with positive energy. Enjoy exquisite design details including the warmth of wood ceilings, a cushy queen bed, a brick kitchen hearth, SMEG appliances and an over-sized penny tile shower. This love nest was made to encourage connection - whether within yourself or with someone you love!

Cape Cod Spectacular Waterfront Cottage

Welcome to our internationally acclaimed and regionally featured cottage located on Lieutenant Island in Wellfleet, MA. It's in a private location with panoramic views and a western exposure featuring beautiful sunsets nightly (weather permitting)! TripAdvisor internationally featured property in July, 2015: Bostondotcom in July, 2016: Business Week in July, 2020. Please contact us for nightly, weekly or long term quotes or discounts. Pricing and lengths of stay are subject to change.

Lake House with Island and boats!

This is a wonderful place to put aside your busy life. No matter the season, our lake home is the feel of relaxation, cozy and comfort. Whatever yours is, you will have the best of all seasons here. Spring flowers popping up, summer water fun, beautiful fall foliage and winter ice-skating, just to name a few. Start the day with a warm cup of coffee watching the sun rise over the trees. Fill the rest with fun and adventures. Finish it with a campfire, s'mores and a nice glass of wine.

Hipster Basecamp | views • fireplace • parking

Welcome to Hipster Basecamp, a thoughtfully curated space where mid-century design meets modern comfort. Whether you're here for business or pleasure, 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.

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Private Guest Room, Kitchenette, Office, & BR

Private downstairs with large bedroom, bathroom & small kitchen, beautiful pond view. Double Bed & Pull-Out Couch, parking in driveway, outdoor fire pit, charcoal grill and outdoor smoking area, 420 friendly. Wifi, 200+ channels HD cable & Apple TV for streaming. Work space with desk chair, small kitchen with coffee maker, mini-fridge, microwave, and toaster. Washer & dryer, shower and bathtub.

Cozy Getaway & More

This is a 27' camper with a very spacious living area which sits on our property. This camper comes with a ton of extra's like beach towels and beach chairs, a cooler for the beach. We do live on a bit of a main road so you will hear cars going by but nothing to bad. We are close to Route 28 which is the main road on the cape and will bring you to one end of the cape to the other end.