Smoking-friendly holiday rentals in Chesapeake

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 | 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 teach coastal vibes!

North End Home with pool, beach & state park.

*NO PARTIES, NO PEOPLE IN THE HOUSE OUTSIDE THE RESERVATION, NO MORE THAN EIGHT ON THE PROPERTY* *THIS IS A QUIET NEIGHBORHOOD; STRICT OBSERVANCE OF 9PM to 9AM QUIET HOURS ARE EXPECTED OF YOU* *OFFENDERS WILL BE KICKED OUT WITHOUT REFUND* *NOT READING THE RULES AND BOOKING YOU STILL AGREE TO THESE TERMS* *DUPLEX STYLE CONDO OWNER OWNS BOTH* *THIS IS CONSIDERED A HOME SHARE HOWEVER YOUR EXPERIENCE IS THAT OF A PRIVATE RESIDENCE* Please do not treat my house like a frat house. Thank you.

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.

Peaceful~Private~Classic Pet Friendly|Ocanoe Houz

Imagine relaxing with the whole family while playing games in the sunroom or backyard! Maybe a girl's getaway by the Bay! Or are the guys hanging out by the fire pit, sipping their favorite spirit with their cigars lit? Our historic home is designed for getaways. Located at Hampton Roads water's edge in Historic Olde Wythe at the end of Virginia's Lower Southeast Peninsula, your stay is less than a minute's walk away to the Indian River Creek and a 5-min walk to the beautiful Chesapeake Bay!

NEW Soundfront Home, Pool, Elevator, Hot Tub, BBQ

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

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. .

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!

Quaint Studio w/pool and resort access

Built on the lush grounds of a former golf course, this quiet resort community is surrounded by the stunning landscape and historic spirit of Williamsburg. A great retreat any time of year, its central location also provides convenient access to explore all the area has to offer. Situated just one mile from Williamsburg's historic area, you'll experience history all around you.