Portsmouth vacation rentals

Guest suite in Chesapeake

4.97 out of 5 average rating, 308 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!

A set of wooden steps leads up to a private entrance, flanked by black wrought iron railings. The area is surfaced with light concrete, and a small outdoor light fixture is mounted near the door, providing visibility in the evening.

4.96 out of 5 average rating, 123 reviews

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, 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 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 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

A pool illuminated by underwater lights radiates a calming blue hue at night. Floating rings rest on the water's surface, and steps lead into the pool from the side. Surrounding greenery is subtly highlighted, creating a serene nighttime atmosphere.

4.94 out of 5 average rating, 115 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Superhost

A brick pathway leads to a white wooden gate, framed by two residential buildings. Green shrubs grow on either side, enhancing the inviting corridor. Utility meters are visible on the walls, providing functional details in this cozy exterior space.

4.82 out of 5 average rating, 102 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

A private entrance is visible at the base of a two-story home, framed by potted plants with blooming flowers. The brick pathway leads to the door, which is complemented by a small window above it. The surrounding area features greenery, enhancing the welcoming appearance.

4.96 out of 5 average rating, 280 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.

The private room features a spacious bed draped with a textured blanket, accompanied by a cozy armchair and an accent chair. A decorative fireplace is situated under a wall with circular art pieces. Natural light filters through the window, enhancing the room's warm tones.

4.98 out of 5 average rating, 110 reviews

English Basement Hide-Away

Private Suite in the heart of Olde Towne, Portsmouth! This historic English Basement style home has a private street entrance. Walking distance from the the waterfront, restaurants, local shopping, Coast Guard Base and Navy Hospital, Atlantic Union Bank Pavillion, ferry into Downtown Norfolk, The Norva, and the Tides Stadium. 9 minute drive to the Rivers Casino. Quick drive to Military Bases, and approx. a 20 minute drive to VA Beach and a 45 minute drive to Williamsburg/Busch Gardens.

Superhost

The kitchen features modern stainless steel appliances, including an oven and microwave. Light countertops are complemented by white cabinets and blue tile accents. A window allows natural light and offers a view of the outdoors. A mix of kitchenware and utensils is neatly organized on the counters.

4.8 out of 5 average rating, 124 reviews

Fun 3BR-2bath with a game room-Near Rivers Casino

Escape to this entertaining 3BR, 2-bath retreat in Portsmouth, VA. Just 4 mins from Rivers Casino and 15 mins from Waterside District. A 30-min drive takes you to VA Beach, ODU, NSU, HU, and CNU. Stay connected with WiFi & Smart TVs. The outdoor space is a treat with a grill & various activities. Indoors, there's a pool table, darts, table tennis, and board games. The renovated kitchen has stainless steel appliances. This home offers a wide range of amenities for a memorable getaway.

A well-equipped kitchenette features vintage cabinetry with decorative accents, a coffee maker, and essential cookware. Large windows allow natural light to illuminate the space, highlighting blue and white dishware on a countertop. A nearby microwave and a laundry area contribute to the functionality of the kitchenette.

4.99 out of 5 average rating, 193 reviews

Elegant Cozy Colonial/Private/Self Check-in

This beautiful 3800 Sq ft Colonial home was built in 1880..previously known as Sycamore Farm, and was featured in Elle Magazines 2000 Christmas edition. The Guest portion of the home is an attached carriage house. The first floor features a large 1134 Sq ft living space that is dedicated entirely to guests. Above it is a locked unoccupied attic. The house is very private and secluded, and is surrounded by bamboo. Private driveway, with space for one vehicle.

A weathered sign indicating '1846 Court House' hangs from a wooden post. The surrounding greenery partially obscures the area, with soft sunlight filtering through the leaves. The backdrop features hints of a historic building, contributing to the charm of the neighborhood.

4.96 out of 5 average rating, 118 reviews

Best location in Olde Towne Portsmouth

This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.

A lively bier garden entrance is framed by vibrant greenery and numerous flower pots. Decorative blue and white signs direct visitors, showcasing menu options. The path is lined with red bricks, adding charm to the inviting atmosphere of this community gathering space.

4.93 out of 5 average rating, 125 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.

4.98 out of 5 average rating, 144 reviews

A wrought-iron gate opens into a private driveway, framed by manicured gardens and blooming trees. The surrounding historical homes showcase a mix of architectural styles, with vibrant brick and siding visible through the lush greenery.

Home in Olde Towne

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!

Superhost

A well-lit hallway features a small desk and chair, accompanied by a decorative plant. The wooden floor extends down the corridor, leading to a carpeted area and doorways that open into other rooms. Soft-colored walls enhance the inviting nature of the space.

4.84 out of 5 average rating, 366 reviews

Spacious 2 bedroom apt in Historic Port Norfolk

If you enjoy homes with lots of history and modern touches, this is the place for you! Our lovely Victorian home was built in the year 1900. We’ve been enjoying all its old world charms since we purchased it in 2016, and we are thrilled to share a part of it with you on your vacations and journeys to exciting new destinations!

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Popular amenities for Portsmouth vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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Other great vacation rentals in Portsmouth

A well-equipped kitchen corner features stainless steel appliances, including a stove and dishwasher. A coffee maker sits on the countertop, accompanied by coffee mugs and sugar packets, with a canister visible in the background. The countertop is adorned with a smooth, light-colored surface.

4.95 out of 5 average rating, 61 reviews

R & R River House

EvanRating, 5 stars1 week ago

Overall this was a great experience, & even with the max amount of guests (6 total) we generally had a lot of space; places to sit & relax; & all felt very comfortable. The view of the lake was also incredible & the amenities provided were top notch. The only criticism I would give is that the listing seems a little misleading about the building being a standalone house vs the town home/condo style house that it actually is. This wasn’t a huge issue but it seems fair to note as the parking was a little confusing once we realized that it was a town house with a parking lot, rather than a standalone one with a driveway. To be fair we did have the max amount of guests & according to Jason this was out of the norm; & Jason did do his best to communicate in finding places to park- but I feel that if there’s any hesitation he might have of that many people being there then the listing may need to be made more clear. Overall though we had a great time & enjoyed the view most of all.

Guest suite in Portsmouth

A spacious shower area features modern tile work in gray tones, complemented by a decorative glass tile border. A built-in shelf provides convenient storage, while a rainfall showerhead is positioned above. Natural light enhances the clean and contemporary design.

4.95 out of 5 average rating, 81 reviews

Historic Hideaway Private Apartment/Suite

EmmaRating, 5 stars1 week ago

Great location if you are wanting something more family oriented, does take about 15-20 minutes to get downtown and depending on the traffic it can take pretty good amount of time to get back to the property, it was a wonderful space for two and perfect for a nice get away, this is a place I definitely would recommend and stay at again.

4.97 out of 5 average rating, 74 reviews

Apartment in Chesapeake

Entire Apartment - No Cleaning Fees!

GregoryRating, 5 stars3 weeks ago

It was a good place to stay and they was very friendly and communication was great. Thank yall for the stay.

A clean kitchen countertop displays a coffee maker and a blender, positioned next to a selection of coffee pods and sugar packets in a neat arrangement. The surfaces are finished in light granite, complementing the modern cabinetry.

4.91 out of 5 average rating, 11 reviews

Home Away From Home

EricRating, 5 stars2 months ago

Place was as described and all info was given and easy to understand definitely worth staying if your in that area

An outdoor space is featured, showcasing a stone fire pit surrounded by six black Adirondack chairs. Lush greenery forms a natural border, and the sky is partly cloudy, creating a bright atmosphere. Posts with string lights are visible, enhancing the appeal of the area.

4.93 out of 5 average rating, 29 reviews

Quiet & Private, Comfy Beds, Fire Pit, & Bikes

DeidraRating, 5 stars3 weeks ago

Had a great girls weekend. It was peaceful and such a cute and quiet neighborhood. We would stay again. It’s located close to everything. The hot water was wonderful. 🤭

A spacious outdoor deck features a large red umbrella providing shade over a glass table and two comfortable seating areas. A stylish lantern sits on the table, complementing the inviting atmosphere of the fenced backyard.

5 out of 5 average rating, 55 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

JulieRating, 5 stars1 week ago

Truly a “hidden gem”! This place was perfect and was more like a home away from home. We felt comfortable and welcomed here. The next time we are in Va Beach we will definitely be checking to see the availability of this place. Thank you, again, Camille

A spacious studio loft is depicted, featuring distinct areas for sleeping and dining. A curtain partially divides the sleeping area with a king-size bed from the kitchen and dining space. Modern appliances and a dining table are clearly visible, alongside warm wooden accents on the wall.

4.95 out of 5 average rating, 59 reviews

Private studio

TaylorRating, 5 stars1 week ago

My bf and I stayed here for our anniversary and we loved it everything was just a 10/10 very private very beautiful we are definitely booking again within the next few weeks

A compact bathroom features light green walls and a high ceiling. A toilet is positioned beside a small sink with a mirror above it. Decorative artwork hangs on the wall, and a roll of toilet paper is accessible nearby.