Holiday houses 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
A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.
Home in Portsmouth
5 out of 5 average rating, 107 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

Guest favourite
Apartment in Portsmouth
4.88 out of 5 average rating, 26 reviews

Private Boutique Apt •W/D• Near Casino & Downtown

Stylish private second-floor apartment in a charming 1915 historic home in Westhaven. 647 sq ft with a queen bedroom, twin daybed room, and a comfortable sofa suitable for one sleeper. Full bath with tub/shower. Living room and dinette for 4. Kitchenette with fridge, microwave, 2-burner cooktop, and coffee maker. In-unit washer/dryer and two TVs. Minutes to Rivers Casino, NNSY, hospitals, Naval Station Norfolk, Beach, and the airport. No pets. No smoking inside. Private entrance & easy parking.

Superhost
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 Portsmouth
4.82 out of 5 average rating, 169 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.

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
4.92 out of 5 average rating, 173 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!

Guest favourite
A well-lit bedroom features a spacious bed with decorative pillows and a cozy throw blanket. Natural light enters through a window, while a standing lamp and a woven basket add functional elements. A ceiling fan and light fixture enhance the room's comfort.
Apartment in Portsmouth
4.85 out of 5 average rating, 155 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!

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
4.96 out of 5 average rating, 123 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
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
4.94 out of 5 average rating, 54 reviews

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.

Guest favourite
A cozy living space features a light-colored sofa with blue cushions and an armchair. A wooden coffee table sits on a patterned rug, accompanied by two lamps providing soft light. Artwork adorns the walls, and a small plant adds a touch of greenery.
Apartment in Portsmouth
4.94 out of 5 average rating, 135 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!

Top Guest favourite
A cozy living area features two dark couches with decorative pillows, a coffee table at the center, and a small desk against the wall. A potted plant adds greenery, and artworks are displayed across the walls. Soft carpeting enhances the comfortable atmosphere.
Apartment in Portsmouth
4.91 out of 5 average rating, 108 reviews

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

Lots of Great Concerts going on Check out the outdoor concerts at the Rivers Casino. Only 1/2 mile away. 600 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice, quiet neighborhood 1/2 mile to the Private entrance and nice, free Private entrance parking for 1 vehicle. Large Sign Visitor Parking Space. One Bedroom w/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 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.
Apartment in Portsmouth
4.94 out of 5 average rating, 139 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.

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 Portsmouth
4.99 out of 5 average rating, 213 reviews

Historic Gem - Walk to Dining, Ferry & Waterfront

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!

Top Guest favourite
A spacious bedroom is presented with a king bed dressed in neutral bedding. Two bedside tables with lamps flank the bed, complementing the light wood furniture. A designated work space, including a desk and chair, is located nearby. Natural light enters through a window adorned with light curtains.
Apartment in Chesapeake
4.97 out of 5 average rating, 115 reviews

Entire Apartment - No Cleaning Fees!

A cozy and comfortable 800 sq ft apartment with available parking in the driveway, a private entrance, in a quiet neighborhood. This will feel like home for the week, weekend, or month you are here. 40 minutes to the Beach, Busch Gardens, Williamsburg, and 15 minutes from Norfolk makes this an ideal and convenient place to stay!

Popular amenities for Portsmouth holiday rentals

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