Holiday rentals in Portsmouth

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Top-rated holiday rentals in Portsmouth

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Smithfield

4.96 out of 5 average rating, 251 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Guest favourite

Guest suite in Chesapeake

4.97 out of 5 average rating, 273 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

Guest favourite

Guest house in Downtown Norfolk

4.98 out of 5 average rating, 601 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Guest favourite

Flat in Portsmouth

4.96 out of 5 average rating, 110 reviews

"The Ponderosa B" - Close to the Casino

Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice family oriented neighborhood about 1/2 mile Rivers Casino! Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign and cones for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth Areana area and 5.9 miles to Downtown Norfolk, 22 miles to VB Oceanfront.

Guest favourite

Apartment in Olde Towne

4.97 out of 5 average rating, 109 reviews

Historic Old Town Portsmouth “Captains Quarters”

Historic charm meets nautical chic! LOCATED ON HISTORIC HIGH STREET in Old Town Portsmouth. Walk to the nearby waterfront! 2 Bedrooms 1 FULL BATH. Open living room. Fully stocked kitchen. Full sized washer and dryer. Staycation-Business-Military. FURNISHED 1000 sq. ft. condominium inside a restored 1912 historic building. The ‘Captains Quarters’ oozes with charm and rustic authenticity. FREE Street and rear parking. NOT appropriate for entertaining. Quiet hours. Makes for happy humans.

Guest favourite

Flat in Olde Towne

4.96 out of 5 average rating, 267 reviews

Cozy Ground Floor Apt in Historic Home

Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

Guest favourite

Guest suite in Chesapeake

4.95 out of 5 average rating, 534 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Guest favourite

Flat in Portsmouth

4.94 out of 5 average rating, 101 reviews

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse

Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

Guest favourite

Guest suite in Downtown Norfolk

4.92 out of 5 average rating, 253 reviews

Cobblestone street apartment with rooftop views!

Historic, Downtown area of Norfolk. Walking distance to shops, restaurants, museums, landmarks, parks, memorials, EVMS, & CHKD. This special residence is on the National Register of Historic Homes, includes a clawfoot tub & rooftop patio (no hold harm). This High Victorian Italian home was built in 1870, with a Mansard roof & features an ornamental cast iron veranda. John Cary Weston built this as a summer residence following the Civil War.

Guest favourite

Flat in Olde Towne

4.92 out of 5 average rating, 101 reviews

Charming cozy apt historic in Old Towne Portsmouth

Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick 5 minute walk and every Saturday morning the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. Let us make your stay stress free and enjoyable.

Guest favourite

Home in Olde Towne

4.98 out of 5 average rating, 125 reviews

Gorgeous Olde Towne historic home - modern updates

Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Guest favourite

Guest house in Phoebus

4.99 out of 5 average rating, 319 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.