Smoking friendly vacation rentals near Chesapeake Bay

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Top-rated smoking friendly rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious bedroom features a wooden ceiling and walls, accentuated by natural light from large windows. A single bed is draped in a deep blue coverlet, paired with a plush chair and leafy plants. A vibrant piece of wall art adds a pop of color to the serene space.
Farm stay in Accokeek
4.97 out of 5 average rating, 168 reviews

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Top guest favorite
Apartment in Upper Marlboro
4.95 out of 5 average rating, 173 reviews

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from Downtown DC & 6Flags.

Top guest favorite
A modern kitchen is highlighted by clean lines and neutral colors. An island with seating is centered, surrounded by a spacious layout. Appliances include a refrigerator and stove, while artwork adorns the walls, contributing to the inviting environment. Ample natural light illuminates the area.
Tiny home in Reston
5 out of 5 average rating, 131 reviews

Pristine 1BR, king bed, hot tub, close to IAD

Luxurious, private and serene. Central location - 1 mile to the Metro, 8 minutes to IAD and Reston Town Center. Dedicated street parking. Close to multiple shops and restaurants. 2 private patios and a side yard. Private use of the spacious hot tub with over-sized towels & luxurious robes. Enormous king-size Sleep Number® bed is exceptional. Chef-worthy kitchen and washer/dryer all yours. Free Netflix, YouTubeTV, and Prime; your own thermostat and very fast WiFi. New construction in 2023. Enjoy!

Superhost
A child stands on the deck of a houseboat, reaching toward a vibrant rainbow arching over the water. The scene captures a serene moment with calm waters reflecting the sky and greenery in the background.
Houseboat in Arlington
4.88 out of 5 average rating, 280 reviews

Warm and Spacious Houseboat with free parking

Enjoy the sights and sounds of nature when you stay in this unique place. Experience the beautiful sunrises and sunsets while the gentle waves help embrace your soul. Well-appointed temperature controlled houseboat. WARM in winter!! Stay at a marina in the DC area. Will send address after booking . Location can vary, usually near Nationals baseball stadium (zip 20024). Average time to Reagan Airport is 15 mins by Uber. Nice bar/restraunt just steps away and bicycle rental end of dock.

Guest favorite
An aerial view of the property features a spacious building surrounded by lush greenery. A gravel path leads to the entrance, and ample outdoor space offers room for relaxation. Nearby, a small shed is visible, nestled among the trees, enhancing the natural setting.
Apartment in Rehoboth Beach
4.88 out of 5 average rating, 394 reviews

Timmy's Treeside Studio Pets Welcome Peeps #420

Timmy’s Treeside in Rehoboth Beach, DE is one of two apts with private entry/deck, on 2 acres, one mile to Rehoboth-Lewes trail and 5min drive to boardwalk/Atlantic Ocean. Queen and a sofa bed for 2-3 humans and all your dogs. Your big deck is a tall perch for fresh air, star gazing, 420 fun, sunbathing, and a dog haven. 2gb Wifi, Roku TV, shower, mini-kitchen/grill/firepit and backyard trail. Tanger Outlets, dog friendly eateries, Revelation Brewery and The Pond are minutes. EZ parking+plugs

Top guest favorite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock
4.99 out of 5 average rating, 301 reviews

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

Guest favorite
A gazebo is nestled among tall trees and greenery, providing a serene outdoor space. The surrounding grass is well-maintained, and a stone pathway leads to the gazebo, enhancing accessibility. Sunlight filters through the trees, creating a calm and inviting atmosphere in the yard.
Apartment in Glen Burnie
4.83 out of 5 average rating, 511 reviews

Quiet Cozy 1 Bdr Apt at BWI Airport

Furbabies Welcome! Yard Oasis! 1 Bedroom Basement suite with private entrance - 12 min. to UM Baltimore Washington Hospital -15 min to Ft. Meade - Great for military - 6 min. drive to BWI Airport terminal -10 min. drive to Casino Live - Driveway parking for 2 vehicles or RV -Wifi/Smart TV with Netflix & YT -10 min drive to Downtown Baltimore -Fully equipped kitchen - Full bathroom w/Soap/Shampoo -Late checkout available w/Fee -Doggie basket -20 miles to Annapolis, Md NO CATS permitted.

Top guest favorite
A scenic view of the Rappahannock River reveals a wide pathway lined with paving stones leading towards a wooden dock. Lush green grass frames the waterfront, complemented by flowering plants in a decorative pot. The sky above is partly cloudy, enhancing the tranquil setting.
Guest suite in Dunnsville
5 out of 5 average rating, 286 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Guest favorite
A view from inside the boathouse showcases a wooden dock extending into the water, with trees lining the bank in the background. Soft lighting is provided by hanging lanterns, and decorative plants add a natural touch to the scene.
Houseboat in Hollywood
4.77 out of 5 average rating, 105 reviews

Charming Rustic Boathouse right on the Water!

Welcome to the Boathouse!! By offering kayaks, swimming, crabbing/fishing opportunity, a beautiful ambiance for drinks and dinner straight on the water and having almost any water adventure right at your fingertips, this glamping (glamour-camping) bungalow on the water is perfect for just about anyone with an adventurous nature-loving spirit! We encourage you to eat what you catch! And even bring your own boat and stay in one of our boat slips! Minutes from Solomons Island by Boat or Car!

Superhost
A studio apartment is shown, featuring a spacious bed with a patterned duvet in the background. A colorful sofa with decorative cushions is positioned beside a low glass coffee table on a patterned rug. A wall-mounted TV and a standing fan are visible.
Apartment in Baltimore
4.79 out of 5 average rating, 500 reviews

Awesome studio tucked away & Centrally located !

Bayview is very close to Greektown, Little Italy, Fells Point and Canton. Each of these commercial developments are no more than 1-2 miles from Drew Street. Restaurants, the waterfront and shopping districts are all located in each of these developments and provide a wide array of tastes and treats. Therefore, if you are a foodie, like wine/beer, antique shops or like to hear a band or singer every once in a while, you can definitely find something to do and travel via Uber, Lyft or Taxi.

Top guest favorite
The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.
Tiny home in Diggs
4.95 out of 5 average rating, 202 reviews

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Guest favorite
A modern living area features a sectional sofa in soft tones, complemented by a coffee table with decorative items. A large television is mounted on a textured wall, and a dining area with a table and chairs is visible in the background. Natural light enters through expansive glass doors.
Home in Oakton
4.96 out of 5 average rating, 113 reviews

Quiet Luxury Home - Modern - King - 20 Min from DC

Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

Popular amenities for smoking friendly rentals near Chesapeake Bay

Quick stats about vacation rentals that are smoking-friendly near Chesapeake Bay

  • Total vacation rentals

    Explore 140 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,220 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Chesapeake Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!

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