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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Top guest favourite
The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.
Guest suite in Chesapeake
4.96 out of 5 average rating, 345 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
A cozy living area is furnished with a beige sofa and a blue armchair. A coffee table with a decorative runner sits in front, surrounded by wooden paneling. Natural light enters from a nearby window, complemented by patterned curtains. Wall art adds subtle character to the space.
Flat in Portsmouth
4.95 out of 5 average rating, 142 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 favourite
The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.
Home in West Park View
4.86 out of 5 average rating, 125 reviews

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

Top guest favourite
A bright sleeping area features a spacious bed with light blankets, accented by a decorative throw. A large circular window allows natural light to fill the space, complemented by dark curtains. A cozy armchair sits nearby, enhancing the room's inviting ambiance.
Guest house in Ghent
4.97 out of 5 average rating, 669 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
A comfortable living room area is featured, showcasing a light-colored sectional sofa with dark blue accent pillows. A dark coffee table is set in front of the sofa. A vibrant world map painting adorns the wall, and natural light streams through a nearby window.
Guest suite in Portsmouth
4.95 out of 5 average rating, 103 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!

Guest favourite
An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.
Home in Portsmouth
4.93 out of 5 average rating, 142 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, 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!

Top guest favourite
A spacious living room is showcased, featuring a comfortable sofa with decorative pillows and a glass coffee table. A flat-screen TV is mounted above a decorative fireplace. Two chairs are positioned nearby, along with a small dedicated workspace illuminated by natural light from a nearby window.
Home in Portsmouth
5 out of 5 average rating, 28 reviews

Water View 1 Bed 1 Bath Retreat

A cozy 1-bed 1-bath water view retreat with a cottage-feel just outside the urban centers of Hampton Roads, close to bases, hospitals, shipyards, downtowns, and beaches. Great for traveling professionals! Conveniently located on the shores of the Elizabeth River in a safe neighborhood, this updated lower unit comes with curated furnishings that will leave you charmed and comfortable. You’ll also enjoy free off street parking, full kitchen, washer/dryer, and a tree swing to enjoy the sunsets.

Top guest favourite
A fully stocked kitchen is presented, featuring a gas stove, a refrigerator, and a microwave. A dark wooden hutch displays dishes and glassware, while a Keurig coffee maker is located on the countertop. Natural light filters in through a nearby window, illuminating the tiled floor.
Flat in Olde Towne
4.96 out of 5 average rating, 298 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
Home in Portsmouth
5 out of 5 average rating, 13 reviews

The Main House

Welcome to Ary’s House! Relax and unwind at my ranch-style home featuring cozy beds, two full bathrooms, and a dedicated workspace with a sleeper sofa for an extra guest. A fully equipped kitchen and dining area stocked with many of your cooking essentials. For added convenience, a washer and dryer are available in unit. Enjoy the private backyard patio, perfect for grilling out or gathering around the fire pit. Our home is family-friendly, We look forward to hosting you!

Top guest favourite
The exterior of a historic home features classic architectural details, including a covered porch with white columns. An American flag is prominently displayed, and mixed flower pots are arranged on the brick pathway. Large windows allow for natural light, showcasing the home’s inviting presence.
Flat in Olde Towne
4.96 out of 5 average rating, 124 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.

Guest favourite
A two-story garage features a sloped roof and a set of double windows on the upper level. A concrete driveway extends beside it, flanked by greenery and a seating area. Sunlight illuminates the space, enhancing its inviting appearance.
Guest house in Chesapeake
4.89 out of 5 average rating, 91 reviews

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work, house hunting, visiting family or friends. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

Top guest favourite
The living room features comfortable navy sofas with decorative cushions and an ottoman in a warm tone. A lamp stands beside a built-in bookshelf adorned with books and decor. Light streams through the windows, and a decorative fireplace adds to the room's character.
Home in Olde Towne
4.98 out of 5 average rating, 176 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!

Popular amenities for Portsmouth holiday rentals

When is the best time to visit Portsmouth?

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Frequently Asked Questions

  • Where should I stay in Portsmouth?

    Make yourself at home in Portsmouth by choosing from our most frequently booked neighborhoods. We have over 510 vacation rentals in Olde Towne, over 270 vacation rentals in Ghent, and over 270 vacation rentals in West Ghent.

  • Are there vacation rentals with a dedicated workspace in Portsmouth?

    Yes! Work meets play with ease at over 300 vacation rentals in Portsmouth featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Portsmouth?

    Four-legged friends are welcome in Portsmouth. Choose from more than 160 vacation rentals for guests traveling with pets.

  • Are there Portsmouth vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Portsmouth, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in private suite rentals in Portsmouth?

    Experience the best of Portsmouth with our private suite rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly condo rentals in Portsmouth?

    Portsmouth has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Portsmouth have wifi?

    Absolutely! We offer over 120 apartment rentals with wifi in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Portsmouth have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Portsmouth have air conditioning?

    Absolutely! We offer over 300 house rentals with air conditioning in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Portsmouth have a gym?

    Absolutely! We offer over 20 house rentals with a gym in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Portsmouth

  • Total holiday rentals

    Explore 520 holiday rentals in Portsmouth

  • Nightly prices starting at

    Portsmouth holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 19,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 160 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wifi availability

    500 of Portsmouth holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Portsmouth rentals

  • 4.7 Average rating

    Portsmouth stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Portsmouth’s top spots include Chrysler Museum of Art, Nauticus and Cinemark Chesapeake Square

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