
Smoking-friendly holiday rentals in Chesapeake
Find and book unique smoking-friendly rentals on Airbnb
Top-Rated Smoke-Friendly Accommodation in Chesapeake
Guests agree: These smoking-friendly rentals are highly rated for location, cleanliness and more.

You’re Grounded
Put your phone down, You’re Grounded Vintage finds and natural earth elements combined with motivating color to encourage you to be your best self. VCRs and vinyl Sunrises and coffee Games and conversations Be present and be grounded You’re Grounded 🏡 House windows are tinted for heat control, privacy, and to enjoy outside views Beds feature feather comforters and 100% cotton sheets and pillowcases 3 miles from Hampton Coliseum, zip to LAFB and NASA, and over the bridge to Norfolk&VB

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
If you enjoy majestic ocean views from almost every room & your own exclusive beach just steps below, Bay Bliss is for you! The panoramic views from this luxury home are unmatched & sure to relax you! Sip coffee from the grand deck or take a soak in the hot tub w/ breathtaking views. Cook/eat in the high-end chef's kitchen or watch a movie on a 75" TV all with stunning views! Wake up in the plush, king-sized bed and enjoy views of the water without having to get up. Your bliss at the bay awaits!

King Bed - 2023 Beach Vacation Fun !
Welcome to your perfect beachside retreat! This expansive 2400 sq ft vacation rental, with a huge gated yard, is ideal for family gatherings, friend reunions, or corporate getaways. Whether you're planning a weekend escape or an extended stay, this stylish and spacious home has everything you need. This tranquil residential neighborhood promises a peaceful stay. Your hosts live nearby and are readily available to assist with any needs. Book your stay today and experience this beach community!

Shipside Suite~Modern~ Fast WI-FI~Cozy
2 bed 1 bath Duplex 950 Sq ft Welcome to Shipside Suite in Portsmouth Virginia! Our apartment has all that you need for your family or business trip. o Smart TV o Stocked Kitchen o Ultra cozy bedrooms o Kid and Pet friendly o Pet o Fast Wi-Fi 5 min walk to the Portsmouth Shipyard 10 min drive to downtown restaurants 10 min drive to Naval Medical center 15 min drive to downtown Norfolk 20 min drive to Outlet Shopping 20 min drive to Ocean View beach 30 min drive to Virginia Beach.

LUX Soundfront Home, Elevator, Golf, HotTub, Games
Discover The Currituck Club Grand, your private soundfront oasis in Corolla's prestigious Currituck Club! This luxurious home is perfect for large groups, offering stunning sunsets over the sound. The mild fall weather is ideal for a dip in the pool or a soak in the hot tub. Inside, an elevator provides easy access to every level, and the home features an arcade and pool table for endless entertainment. With expansive decks, this is your ultimate fall getaway. Book your unforgettable stay

King Bed | Front Porch | End-Of-Street Property!
Monthly Fall - Spring discount! Cozy Home Just 2 Blocks from the Beach! Enjoy a stay where comfort meets coastal charm, plus a few thoughtful touches you’ll love: • A host who cares about your experience! • Relax with your morning coffee on the front porch while watching the birds and squirrels! • Tucked away on a quiet dead-end street for extra privacy • Just 1.5 miles from restaurants, breweries, and local activities • Pet-friendly — bring up to 2 pets Experience the coastal vibes!

The Bartlett Inn
Welcome to The Bartlett Inn, a charming Cape Cod home built in 1948, nestled in the serene Green Acres neighborhood of Portsmouth, VA. Enjoy the timeless appeal of hardwood floors, traditional Cape Cod architecture, and the peaceful ambiance of a well-established yard and neighborhood. Conveniently located near parks, shopping, and dining options, casino, hospitals, bases and so much more! The Bartlett Inn offers a delightful blend of nostalgia and comfort that welcomes anyone home.

Ocean Sounds & Wild Horses!
Welcome to your secluded oasis on the pristine shores of the Outer Banks, nestled along the tranquil 4x4 beach. The accommodation boasts 2 bedrooms, each designed with your comfort in mind. Sink into plush bedding after a day of sun-soaked adventures and fall asleep to the gentle lullaby of the ocean. Accessible only by 4x4 vehicles, your beach house offers unparalleled seclusion, ensuring a peaceful and exclusive retreat away from the hustle and bustle of everyday life. .

Heutte House
Great 3 bedroom home with full amenities so you and your family can have the best stay! Our home includes 3 bedrooms, 2 bathrooms, an outdoor lounging space, and a fully loaded game room for the kiddos (or adults)! We are conveniently located 2 miles from the Norfolk airport, Botanical Gardens, Shopping Outlets, Norfolk Naval Bases, and most importantly the beach! 🐚 –We have a strict NO party or event policy. –Smoking or vaping outside only.

Bells Island, w/pool on the water.
Bring your boat, or jet ski and take off from the backyard. We are on the water and have a pool 2 kayaks and 4 bikes to keep everyone busy. Or relax on the hammock. This house accommodates 8-10 people easy. Kids will love the pool! Have bonfires roast marshmallows. Make great family memories here. It’s peaceful and safe fun for all. Water views surround. Walks are amazing here. We are 45 min from the beach in OBX dogs are welcome!

The Canvasback Cottage
This unique place has a style all its own. Cottages on the Point was launched in 2018 and offers timeless interior styling and stunning resort style outdoor views. The property features a seasonal (Mid-April to the end of October) 14,000 SF outdoor tiki bar with a shared saltwater pool with swim up bar, outdoor kitchen, and live music. The residences are adjacent to the tiki bar deck and include open layouts, terraces, and custom décor.

The Chesapeake St Retreat - Pet and Kid Friendly
The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10, a fenced in back yard for your furry friends. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!
Popular amenities for Chesapeake Smoke-Friendly Accommodation
Smoking-friendly apartment rentals

Virginia Beach, Getaway

Cozy Apartment In Virginia Beach

Quaint Studio w/pool and resort access

Shipside Suite~Modern~ Fast WI-FI~Cozy

Affordable 1000 Sq ft 2 bd 2 Bath Apartment
Smoke-Friendly Holiday Houses

Milly's Place

REFLECTIONS OF THE HEART

Upstairs Room in Ocean View

NY Bebop Qn, Full Kitchen, W&D, AC & Safe Rm#1

Laid-Back Lakeside Getaway, 500+ Reviews

Traditional 1BR Home in Hampton, VA

Downtown Hampton Spacious Waterfront

LUXURY 1BR-FREE PARKING- Airport 5min
Other smoking-friendly holiday rentals

Upstairs private room with water view. Pet ok pool

Wyndham Kingsgate Resort: 2 Bedroom Suite

Room w/ Queen bed private bath

HIPPY ROOM ESCAPE

Comfort Eco Qn w/ Full Kitchen, W&D, AC & Safe#2

Historic Capitol Landing (Rm#3)

Historic Capitol Landing (Rm#1)

Historic Capitol Landing (Rm#2)
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $140 NZD | $176 NZD | $98 NZD | $108 NZD | $124 NZD | $108 NZD | $126 NZD | $140 NZD | $140 NZD | $114 NZD | $116 NZD | $176 NZD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about holiday rentals that are smoking-friendly in Chesapeake

Total holiday rentals
Explore 30 holiday rentals in Chesapeake

Nightly prices starting at
Chesapeake holiday rentals start at $36 NZD per night before taxes and fees

Verified guest reviews
Over 670 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesapeake rentals

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Smoking-friendly rentals Virginia
- Smoking-friendly rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Norfolk Botanical Garden
- Chrysler Museum of Art
- James River Country Club
- Cape Charles Beachfront
- Wilkins Beach
- Red Wing Lake Golf Course
- Little Creek Beach




