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.

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, 302 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!

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!

Top guest favorite
A rustic cabin is nestled among trees, elevated on a wooden deck. The vibrant red roof contrasts with the surrounding greenery. Four red chairs are arranged on the deck, providing a view of the natural landscape. Sunlight filters through the leaves, creating a serene ambiance.
Cabin in Airville
4.98 out of 5 average rating, 112 reviews

"ON THE ROCKS CABIN" the perfect getaway for 2!

Cabin is very charming, but rustic. Kitchen has full size frig, microwave, toaster oven, hot plate, toaster+ keurig. Coffee, condiments, soap & shampoo provided. There is a gas grill. Guests provide their qs sheets, towels, campfire wood & drinking water. A variety of dvd’s & games, hot water in & outside shower & tub. Tubes for floating provided, swim your own risk. Fire pit, creek is stocked. Steps to deck overlooking the creek.Trash goes home with guests, smoking on the decks only.

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.

Top guest favorite
The exterior of a two-story home is presented, featuring a warm yellow facade and multiple large windows. A welcoming porch with a white railing provides access to the front entrance. The surrounding area is landscaped with gravel and illuminated by soft outdoor lighting.
Home in Washington
4.99 out of 5 average rating, 263 reviews

5-BR Home near DC Metro -Free Parking/Full Kitchen

RARE FIND — Main-Level Bedroom & Bath with No Steps! Welcome to your stylish D.C. retreat! This fully renovated 5-bedroom, 4-bathroom home offers 3,500 sq ft of open-concept living, just 3 minutes from the Metro and 10 minutes from the White House. Enjoy free street parking. Perfect for families or business travelers with a main-floor bedroom, chef’s kitchen, double living rooms, fast Wi-Fi, and smart TVs. Book your stay today and experience D.C. in comfort and style.

Top guest favorite
A covered patio is illuminated by string lights, featuring a gas fire pit surrounded by seating. A barrel sauna stands prominently, with a reflective door, offering a unique design. The gravel surface complements the outdoor space, creating an inviting atmosphere for relaxation.
Home in Silver Spring
4.96 out of 5 average rating, 104 reviews

Sauna, hot tub, great outdoor space!

Escape to our serene suburban retreat in Silver Spring, Maryland, where this 3-bedroom, 2-bathroom home awaits you on a fenced half-acre lot. Immerse yourself in comfort and luxury with amenities such as a private hot tub, sauna, gas fire pit and the expansive outdoor space. Pet friendly w/non-refundable pet deposit. No more than 6 guests at any time, no parties. Please include a list of all guests, per Montgomery county regulation, when you book. Thanks!

Top guest favorite
A cozy living area presents a light brown couch adorned with colorful cushions and a decorative throw. Two accent chairs sit across from the couch, positioned on a patterned area rug. Natural light filters through sheer curtains covering a large window, illuminating the space.
Home in Ocean Pines
4.97 out of 5 average rating, 105 reviews

Sweet Retreat

Sweet Retreat is conveniently located in Ocean Pines, Maryland. The premiere residential and resort community of Ocean Pines is located eight miles inland from the ocean resort town of Ocean City. Ocean Pines has over 9 miles of waterfront property and 3,000 acres of wooded areas. Community amenities include beaches, a yacht club, golf course, community center, a Beach Club Pool and other community pools. Passes are available at ocean Pines Association.

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 R170 ZAR 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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