Smoking-friendly holiday rentals in Hampton Roads

4.67 out of 5 average rating, 3 reviews

You’re Grounded

Put your phone down, You’re Grounded Secondhand 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 ORF&VB

A vibrant red swing hangs from a covered porch, inviting relaxation while enjoying the fresh air. Surrounding the swing, a pair of dark wicker chairs add additional seating options. The spacious deck features wooden flooring and is framed by white railings.

4.8 out of 5 average rating, 64 reviews

Downtown Hampton Spacious Waterfront

NOSTALIC yet MODERN waterfront home, people-watching porch, large bedrooms, ample parking, deck and gazebo, & 2023 two-zone HVAC system. Downtown Hampton & walking distance to the Historic Hampton Post Office (weddings) & the Landing Hotel. Minutes from Hampton University, Yacht Club, Buckroe Beach, Fort Monroe, Christopher Newport, Hampton Coliseum, NASA, & Langley Air Force Base. 20 to 30 minutes to the College of William & Mary, Virginia Beach, Norfolk, Airports, Bush Gardens, & Water County

A spacious living and dining area features warm wooden flooring. The kitchen with dark wood cabinetry is equipped with modern appliances. A light-filled seating area is arranged with a dark sectional sofa and decorative cushions, complemented by a coffee table and nautical-themed decor.

4.93 out of 5 average rating, 74 reviews

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!

4.77 out of 5 average rating, 70 reviews

A bright living area features a light-colored sofa, a woven coffee table, and a dining set with transparent chairs. Natural light filters in through the large windows with white curtains, while a ceiling fan provides air circulation. The kitchen is subtly visible in the background.

Apartment in Portsmouth

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.

A cozy outdoor area features multiple seating arrangements around a stone fire pit. Potted orange and yellow chrysanthemums add a pop of color, complemented by string lights above. The fenced yard offers ample space for relaxation and gatherings.

4.8 out of 5 average rating, 51 reviews

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!

5 out of 5 average rating, 12 reviews

A living room features green sofas arranged around a large coffee table, creating a welcoming atmosphere. A wooden divider partially separates the space from the kitchen area. Natural light brightens the room, highlighting decorative plants and a television positioned on a media console.

Home in Norfolk

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!

4.97 out of 5 average rating, 34 reviews

A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.

Home in Portsmouth

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.

A wooden cabin constructed from rich timber is showcased amidst a natural setting. The structure features large windows that allow for natural light and a welcoming porch with sturdy steps leading to the entryway.

Cabin in Williamsburg

4.77 out of 5 average rating, 90 reviews

Log Cabin

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.

5 out of 5 average rating, 23 reviews

A spacious bedroom is presented, featuring a luxurious king size bed dressed in patterned linens. Comfortable seating options include a cozy armchair and a leather sofa. Natural light floods the room through large windows, with a private balcony offering views of the serene surroundings.

Guesthouse in Suffolk

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.

4.83 out of 5 average rating, 121 reviews

A bright and spacious living area features comfortable seating on a large sofa and armchairs. A flat-screen TV is mounted on the wall across from the seating. Natural light enters through multiple windows, and a decorative plant adds a touch of greenery to the room.

Home in Norfolk

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!