Smoking-friendly vacation 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!

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!

Comfortable retreat w/ backyard & parking

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.

Ocean Sounds & Wild Horses!

Welcome to your secluded oasis on the pristine shores of the Outer Banks, nestled along the tranquil 4x4 beach. **Accessible only by 4x4/ AWD SUV vehicles** 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. Your beach house offers unparalleled seclusion, ensuring a peaceful and exclusive retreat away from the hustle and bustle of everyday life. .

The Chesapeake Guesthouse

Your group will enjoy the convenience of being centrally located in the Greenbrier area of Chesapeake in this well appointed, spacious ranch style home. This property has three well appointed bedrooms, 2.5 baths, fully equipped eat-in kitchen, dining room - and a flex space we like to call "The Green Room". There is off-street parking for up to four vehicles and a huge backyard. All located within minutes of major highways, hospitals, shopping, eateries, entertainment and military bases.

Country Escape - Next DOOR - Hidden Gem

Relax at this tranquil country retreat! This 1,100 sq ft loft sits above a garage behind the main Country Escape rental. The deck overlooks a wooded, park-like yard, giving it a cozy treehouse feel. Thoughtful décor and repurposed doors (the inspiration for its name, “Next Door”) create a welcoming space. Perfect for unwinding and recharging while still close to local attractions. From the time you walk in you will feel the warmth and comfort of a country escape.

Log Cabin - Williamsburg Pet-Friendly, Heated Pool

Pet-friendly log cabin with 2 rooms, A/C & heat, free Wi-Fi, and cable TV. Includes a queen bed, breakfast bar, mini-fridge, microwave, and ceiling fan. No bathroom inside, but just steps from our first-class, professionally cleaned bathhouse. No kitchen. Outside: charcoal grill, picnic table, and fire ring. $20 per pet per stay. Linens/pillows not included—bring your own or rent a set for $20. Enjoy our 85° heated pool, free game room, and playground.

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.

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!!

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.

Walk to Beach | Quiet dead-end street| King Bed

Welcome to our cozy beach home just 2 blocks from the bay — close enough for beach walks and sunsets, but still quiet enough to sleep like you don’t have 37 unread emails! We enjoy hosting and want guests to feel comfortable, relaxed, and at home during their stay. Whether you’re here for a beach trip, work, or a quick getaway, we’d love to host you. If you see something missing before your stay, please let us know!