Smoking-friendly holiday rentals in Massachusetts

The Cotuit Bungalow

Our cozy Cotuit Bungalow is one of the Cape’s newest, coolest guesthouses built in 2017 to accommodate singles & couples seeking the perfect Cape Cod get-away (2 guests maximum). Located in the residential village of Cotuit, the bungalow comes fully loaded - queen-sized bedroom, separate bathroom w/shower, spacious screened-in deck, wet-bar/microwave/fridge, a/c, cable & WiFi, fire pit, outdoor shower and private parking. Bed linen is provided, but please bring your own towels (bath & beach).

Cozy Entire Unit Condo close to UMASS Lowell

My place is close to restaurants, UMASS. Lowell, and almost anything you need. You’ll love my place because instead of having a spare room in someone's house, you get an entire condo and privacy available to you (owner lives in separate unit). The unit includes basic amenities included (toiletries, bedding etc). In addition, the unit comes with a PlayStation 4 for the kids (or the husband/boyfriend) to keep them busy :) My place is good for couples, solo adventurers, and business travelers.

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.

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.

Pet friendly, cozy, modest cape, two bedrooms

You, those in your party and your pet(s) will have this modest, quirky, cozy, cape style, home all to yourself. There are two bedrooms and a pullout loveseat on the main level. It is accessible to all Berkshire cultural sites including Mass MoCA and The Clark. Conveniently located in the Northwestern corner of the state, the Vermont state line is less than 5 minutes away and the New York state line is less than 15 minutes away. The Williams College campus is within walking distance.

Hipster Basecamp | fireplace • views • parking

Hipster Basecamp is the perfect place to chill whether you are here for work or play. Mid-century modern design, a two-sided fireplace, free parking, new orange Smeg appliances, and a spa-like bathroom with a ceiling-mounted shower and towel heater. Whether you're feeling barista or mixologist, there's everything you need to perfect your craft and enjoy a drink on the deck. Fall in love with the original art from our curated collection and purchase a painting to bring home.

Indian Lake House

Embark on a journey of tranquility within this expansive and harmonious abode. Featuring meticulously designed interior and exterior areas for communal bonding, as well as 420 spaces dedicated to relaxation and meditation, this residence promises to provide the ultimate rejuvenating escape you seek. Whether your stay is extended or brief, and conveniently situated just steps away from the lakeshore, this haven is primed to offer you an unparalleled sanctuary of reprieve.

True Shangri-la, Country Retreat

Modern comforts in this gorgeous, spacious home on 50 acres with a view of the Vermont foothills. Enjoy the pond, fire pit, streams, gardens, deck and access to the sweet town of Ashfield - be out in the woods without being in the middle of nowhere! Fiber Optic high speed internet is wired so you can reliably work and relax. Mass Certificate #C-12336793-003 This listing does require a signed rental agreement (sorry for the formality but my insurance company insists!)

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.