Holiday houses in Portsmouth

Guest suite in Chesapeake

4.97 out of 5 average rating, 310 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!

4.96 out of 5 average rating, 124 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.

Guest suite in Portsmouth

4.95 out of 5 average rating, 83 reviews

Historic Hideaway Private Apartment/Suite

You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

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!

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!

4.96 out of 5 average rating, 281 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.

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.

4.95 out of 5 average rating, 59 reviews

Private studio

Our renovated studio loft is a charming second-story unit situated above the detached garage at the back of our property. The space features a comfortable king-size bed and a full size sleeper sofa. For added privacy, the master sleeping area can be separated by curtains. Enjoy entertainment from any part of the loft with a 55-inch TV mounted on a swivel. The unit also includes a washer and dryer for your convenience. Our property is family-friendly, and we look forward to hosting you!

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.

4.93 out of 5 average rating, 126 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.

4.95 out of 5 average rating, 62 reviews

R & R River House

Have a peace of mind when you rent this luxury condo with beautiful water views. Totally remodeled condo with high-end finishes. This home is perfect for a couple getaway or family for fun with the nearby city park (1 mi). The peaceful condo is located close to the Casino (4.5 mi), Downtown Portsmouth (7 mi), Waterside (7.6 mi), and Virginia Beach (25 mi). Be amazed with this nestled away condo in safe neighborhood.

4.79 out of 5 average rating, 240 reviews

Waterfront Maryview/Naval Hosp Casino close to all

This lovely, quaint home has been completely updated for your comfort. The great room is bright and open. The home is located on the Elizabeth River in an upscale neighborhood with a large yard. This is perfect for a family vacation, or a long weekend. There is an attached mother-in-law suite in the rear of the house. This is rented out separately. It has a private entrance at the rear of the house.

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Other great holiday rentals in Portsmouth

4.98 out of 5 average rating, 265 reviews

Private room in Norfolk

Military - Active/Retired/Family at Cape Defoe B&B

ChristineRating, 5 stars3 weeks ago

I stayed at Mark’s place while visiting my daughter, who’s in the Navy, and it was the perfect spot for some peaceful downtime. Even though it’s a shared home, the bedroom and bathroom felt very private and exceptionally clean. I was comfortable the entire time and slept well. The house itself is like walking into an art installation—colorful, unexpected, and full of personality. You never quite know what light or feature will come to life next, which made it fun and memorable. Both hosts are clearly creative souls with a flair for design. The backyard was my favorite part—lush with plants, fountains, and statues, all backing up to the Chesapeake waters. At night, it turns into a magical light show with just the sounds of nature and water features. So peaceful and calming. They even had a little breakfast area set up with bakery items and coffee—such a thoughtful touch. I’d definitely stay again and recommend it to anyone looking for a one-of-a-kind and restful experience.

TanellRating, 5 stars2 weeks ago

New place to stay

Portsmouth's Finest

I needed a last minute accommodation and Chanelle did just that. I’m a native to the Chesapeake/ Portsmouth area and was in town for an event and Chanelle’s place was cozy and full of character. I will definitely stay again!

5 out of 5 average rating, 7 reviews

Comfortable Portsmouth Classic

AliciaRating, 5 stars3 weeks ago

A nice private space with a wonderful large smart TV, good quality washer and dryer that is convenient and a nice kitchen. It's basically an old bungalow home upgraded or modernized, decked out. Friendly neighbors. It's quiet at night

4.92 out of 5 average rating, 281 reviews

Private room in Norfolk

Room close to Ghent ODU EVMS military base

CharlesRating, 5 stars2 weeks ago

Elita’s place was great. Accurate description, easy instructions, and most importantly- a clean and quiet room. The bed was great and I easily was able to sleep soundly. Communications was good … I will stay here again for easy walking to Ghent and ODU neighborhoods.

4.82 out of 5 average rating, 11 reviews

The Lounge

WilliamRating, 5 stars2 weeks ago

Ameenah was a great host and the home was very nice and clean.

4.98 out of 5 average rating, 310 reviews

Private room in Ghent

The Owl Room in Late 1800s Historic House

SergeRating, 5 stars3 days ago

What an incredibly beautiful, well kept home with so much personality. My wife and I stayed in the Owl Room for 2 nights and it was absolutely perfect. The bed was so comfortable and the AC worked beautifully. We also loved the tea and coffee that was left out for us. This felt like what Airbnb used to be before people started getting greedy. Thank you again so much for having this available.