Holiday houses in Portsmouth
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Quick stats about holiday rentals in Portsmouth
Total holiday rentals
Explore 490 holiday rentals in Portsmouth
Nightly prices starting at
Portsmouth holiday rentals start at $34 NZD per night before taxes and fees
Verified guest reviews
Over 20,100 verified reviews to help you choose
Family-friendly holiday rentals
250 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 150 rentals that welcome pets
Holiday rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
300 properties have a dedicated workspace
Wi-Fi availability
470 of Portsmouth holiday rentals include Wi-Fi 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
Top-rated holiday rentals in Portsmouth
Guests agree: these stays are highly rated for location, cleanliness and more.
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
Mid-Century Modern Old Town Portsmouth 3bd/2.5 bth
In the heart of Colonial Portsmouth, VA, on a quiet one-way street -- nestled among homes that date back to the American Revolution & Underground Railroad -- you have found this unique gem... classic and unassuming on the outside, newly rebuilt and designed within. Glasgow Modern, the perfect home-away-from-home. Adjacent to an amazing park, blocks away from the water. We live here 6 months of the year, so the house has everything you need. Dine, Play, Explore, Enjoy... Our home is your home!
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!
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!
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!
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.
Riverfront 3BR Retreat • Near Rivers Casino
🏡 Peaceful riverfront home on the Elizabeth River 🛏️ Sleeps up to 6 guests across 3 comfortable bedrooms 🌿 Spacious backyard overlooking the water 🍽️ Fully stocked kitchen for home-cooked meals 📶 Fast Wi-Fi ideal for work and streaming 🧺 In-home washer and dryer 🎰 Only 8 minutes to Rivers Casino Portsmouth ⚓ Close to Olde Towne Portsmouth, Norfolk & local attractions 🚗 Convenient driveway parking 🌅 Quiet neighborhood perfect for relaxing getaways
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!
Contemporary 5 BR, 4BA, Over 3500 SF Water Front
Luxurious contemporary 5 bedrooms, 4 bathrooms over 3500 SF waterfront home with direct access to Chesapeake Bay. Kick back and relax in this calm, stylish space with water views throughout. This home also offers a dock in the back where guests can do fishing, crabbing and docking boats. It is conveniently located in Churchland area of Portsmouth, 15 minutes away from River Casino and close by shopping centers and restaurants.
Escape to the water!
Beautiful newly renovated home with lake access and water views. 4 bedroom, 2 bath with front and back porches. Master suite upstairs and 3 bedrooms downstairs with plenty of room for families to enjoy. Equipped with 2 kayaks for your enjoyment! Take about 50 feet right to the water and enjoy the outdoors with family and friends.
Condo Near Portsmouth Naval on Webster Avenue
Charming upstairs unit of a duplex property located in the historic Park View community of Portsmouth, VA. Close to local hospitals, Rivers Casino, and the Portsmouth Shipyard. Enjoy a blend of vintage character and modern comfort, perfect for travel nurses, professionals, or visitors exploring the area.
Spring Hill Guest Cottage - Portsmouth
Two room guest house with full bath and 1/2 bath, kitchenette and sitting room Sits on 9 acres. Adjacent to an occupied 300+ year old house that dates back to the 1700s. Shared access to in-ground pool and adjacent Jacuzzi with owners, but you will have exclusive use during your booking.
Popular amenities for Portsmouth holiday rentals
Other great holiday rentals in Portsmouth
Play + Stay in Churchland | Private & Cozy Home
The Bartlett Inn
Cozy Modern Retreat, Peaceful Stay Near Everything
Tudor Treasure in Olde Towne
Elegance Escape on Saunders Dr
In-law… Sweet!
Private Boutique Apt •W/D• Near Casino & Downtown
A Ray of Sunshine
When is the best time to visit Portsmouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 NZD | $161 NZD | $172 NZD | $180 NZD | $197 NZD | $207 NZD | $200 NZD | $185 NZD | $172 NZD | $175 NZD | $173 NZD | $175 NZD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Frequently Asked Questions
What are the best places to stay in Portsmouth?
Olde Towne is often recommended for its historic architecture, walkable streets, and access to eateries and galleries. Vacation rentals near the Elizabeth River waterfront are also popular for their scenery and proximity to local attractions.
What are the best things to do in Portsmouth with kids?
The Children’s Museum of Virginia is frequently suggested for interactive exhibits, while Portsmouth City Park has playgrounds and open space for games. Families also enjoy local boat tours or strolls along the Elizabeth River waterfront.
What are some of the best things to do in Portsmouth?
Explore local history at the Lightship Portsmouth Museum, stroll the murals and cafés of Olde Towne, or enjoy family-friendly activities at the Children’s Museum of Virginia. Waterfront parks are popular for picnics and relaxing by the river.
How is the weather in Portsmouth?
Portsmouth has mild winters around 34–53°F (1–12°C) and warm, humid summers reaching 73–89°F (23–32°C). Rain is more common from June through September, so a light raincoat or umbrella can be helpful during these months.
When is the best time to visit Portsmouth?
Late spring and early autumn are frequently suggested for visiting Portsmouth, with comfortable weather around 60–77°F (16–25°C) and a mix of outdoor festivals. Summer draws visitors for waterfront events and longer daylight hours, though humidity can rise.
What are the best places to visit in Portsmouth?
The Lightship Portsmouth Museum, Children’s Museum of Virginia, and Portsmouth Art & Cultural Center are among the most popular cultural sites. Olde Towne stands out with its historic buildings, murals, and lively events.
What are some hiking trails in Portsmouth?
You can explore nature trails at Paradise Creek Nature Park or stroll the shaded paths of Portsmouth City Park. These spots have gentle terrain suitable for relaxed walks and birdwatching.
What are some family activities we can do in Portsmouth?
Families can explore interactive exhibits at the Children’s Museum of Virginia, have a picnic at Portsmouth City Park, or join a riverfront boat tour. The city’s murals and public art also make for a fun outdoor scavenger hunt.
What are some of the best day trip ideas from Portsmouth?
Explore Norfolk’s museums and vibrant arts scene, visit state parks known for hiking and wildlife, or discover the historic districts in neighboring coastal cities. The surrounding Hampton Roads area has multiple locally rooted attractions.
Are there any pet friendly accommodations available in Portsmouth?
Many Portsmouth vacation rentals welcome pets, especially in neighborhoods with nearby parks or green spaces. Olde Towne and waterfront areas often have walkable streets, making outings with pets convenient.
What are some local tips for visiting Portsmouth?
Explore Portsmouth’s Olde Towne for shaded streets, murals, and independent shops, and consider the Elizabeth River waterfront for scenic walks. Local ferries can provide a unique city perspective, and weekday mornings are often quieter in museums or cafés.
What is Portsmouth known for?
Portsmouth is known for its maritime history, historic Olde Towne district, and the Children’s Museum of Virginia. The city also stands out for waterfront festivals and locally rooted cultural traditions.
What are the best hidden gems to explore in Portsmouth?
Visit the Lightship Portsmouth Museum for maritime history or seek out local murals tucked throughout Olde Towne. Paradise Creek Nature Park is also a quieter spot for birdwatching and wetland views.
What are the best foods to try in Portsmouth?
Portsmouth is known for regional seafood like oysters and blue crab, as well as Southern-inspired dishes such as shrimp and grits or fried green tomatoes. Bakeries around Olde Towne are also popular for seasonal pies and desserts.
What should I bring for a trip to Portsmouth?
Pack comfortable walking shoes for cobblestone streets and riverfront paths, and consider layers, as temperatures shift from cool mornings to warm afternoons. A light rain jacket is helpful, especially in summer and early spring.
What is the nightlife in Portsmouth like?
Nightlife in Portsmouth centers around Olde Towne, where you can explore local pubs, live music venues, and late-night eateries. Evening walks along the waterfront also draw visitors for a relaxed atmosphere and river views.
What are the most popular events or festivals in Portsmouth?
Portsmouth has waterfront music festivals in summer, art walks and cultural celebrations in Olde Towne, and a holiday parade in late autumn. Seasonal markets and jazz events are frequently suggested as well.
Are there family friendly vacation rentals in Portsmouth?
Portsmouth has many family-friendly vacation rentals, especially near Olde Towne, the city park, and scenic neighborhoods. Look for options with extra space and kitchens to make your stay comfortable for all ages.
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