A marina with several boats docked, surrounded by modern buildings including a Hilton hotel and a SunTrust building.

Portsmouth Holiday Rentals

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Our top choices for Portsmouth holiday rentals

1. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
The price is NZ$328
includes taxes & fees
1 Oct - 2 Oct
Private 1 Bed Apt - Historic Olde Towne Portsmouth

2. Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (55 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is NZ$488
includes taxes & fees
1 Oct - 2 Oct
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

3. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (47 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is NZ$604
includes taxes & fees
6 Oct - 7 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

4. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is NZ$478
includes taxes & fees
20 Oct - 21 Oct
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

5. Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
Portsmouth
9.2 out of 10, Wonderful, (27 reviews)
"Great small home would rent again"
United States
Ronnie B.
The price is NZ$616
includes taxes & fees
3 Oct - 4 Oct
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

6. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
The price is NZ$503
includes taxes & fees
13 Oct - 14 Oct
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

7. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.8 out of 10, Excellent, (12 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
The price is NZ$422
includes taxes & fees
1 Oct - 2 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

8. Spacious Portsmouth Getaway w/Game Room

Spacious Portsmouth Getaway w/Game Room
Portsmouth
7.0 out of 10, Good, (2 reviews)
"This property is in a great location near beach and also casino"
United States
JOSIE G.
Spacious Portsmouth Getaway w/Game Room

9. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Great property not too far from the beaches! Between the pool, hot tub, mini golf, and theater room, our family had plenty to do at the house when we weren't out exploring Virginia Beach. Owner was quick to respond to any questions or needs as well."
United States
Erin W.
The price is NZ$1,165
includes taxes & fees
4 Oct - 5 Oct
Wooded Wonderland

10. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (107 reviews)
"The front desk staff were friendly, welcoming and helpful. The property and room were very clean and quiet. The bed was comfortable, and the room was spacious with a full kitchen. Location is very convenient to restaurants and shopping. Highly recommend this property!"
United States
Kimberly
The price is NZ$241
includes taxes & fees
12 Oct - 13 Oct
stayAPT Suites Suffolk-Chesapeake

11. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
The price is NZ$515
includes taxes & fees
3 Oct - 4 Oct
Guesthouse in ideal location with private entrance

12. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (23 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is NZ$245
includes taxes & fees
1 Oct - 2 Oct
stayAPT Suites Hampton

13. Sojourn's Harborage S

Sojourn's Harborage S
East Ocean View
9.4 out of 10, Exceptional, (3 reviews)
"Clean and pet friendly one bedroom apartment with everything we needed for an amazing weekend away. Highly recommend."
United States
William
The price is NZ$472
includes taxes & fees
29 Oct - 30 Oct
Sojourn's Harborage S

14. Sojourn's Harborage Seal Suite

Sojourn's Harborage Seal Suite
East Ocean View
8.6 out of 10, Excellent, (4 reviews)
"We utilized this apartment for a weekend stay and could not promote this property enough. It is in a nice area and right by the beach. The apartment had just what we needed and was very clean and cute. Definitely would recommend!"
United States
Rhylanne B.
The price is NZ$588
includes taxes & fees
1 Oct - 2 Oct
Sojourn's Harborage Seal Suite

15. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.6 out of 10, Exceptional, (13 reviews)
"The property is spacious and conveniently located near the beach and restaurants. It is family-friendly and the host is exceptionally communicative. I plan to return in the future."
United States
Sheryll
Bright 3-bedroom beach house with AC in charming Norfolk

16. Ice Ice Baby | Downtown Newport News!

Ice Ice Baby | Downtown Newport News!
Downtown Newport News
9.6 out of 10, Exceptional, (21 reviews)
"Over all stay was comfortable... and convenient! Traffic was good into Newport news... Good stay"
United States
Adria K.
The price is NZ$450
includes taxes & fees
1 Oct - 2 Oct
Ice Ice Baby | Downtown Newport News!

17. Cozy 1-bedroom barn in marvelous Hampton with AC

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
10.0 out of 10, Exceptional, (1 review)
The price is NZ$350
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-bedroom barn in marvelous Hampton with AC

18. Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (304 reviews)
"Great host! We had a great time!"
United States
Jessie m.
The price is NZ$746
includes taxes & fees
5 Oct - 6 Oct
Norfolk Beach Cottage Rental

19. SEA-clusion4 cozy apartment across the street from the beach

SEA-clusion4 cozy apartment across the street from the beach
Cottage Line
The price is NZ$257
includes taxes & fees
6 Oct - 7 Oct
SEA-clusion4 cozy apartment across the street from the beach

20. Sojourn 2 BR Luxury Beach Side Suite Surf Suite

Sojourn 2 BR Luxury Beach Side Suite Surf Suite
Cottage Park
8.8 out of 10, Excellent, (3 reviews)
"Great location, comfy bed, comfy beach chairs and plenty of towels provided. Very communicative property manager - overall a wonderful stay and we’ll be back!"
United States
Liza M.
The price is NZ$697
includes taxes & fees
6 Oct - 7 Oct
Sojourn 2 BR Luxury Beach Side Suite Surf Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Portsmouth Hotel Reviews

Find out more about Portsmouth

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portsmouth holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portsmouth. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portsmouth. Seeing all the best attractions is bound to make you fall in love with Portsmouth. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portsmouth short-term rentals, that won’t be hard to do.

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Frequently asked questions

Are there holiday rentals in Portsmouth?

Yes, there are holiday rentals in Portsmouth close to Children's Museum of Virginia, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and museums in Portsmouth. Make sure you allow time to enjoy the riverfront during your holiday.

What are some of the best holiday rentals that Portsmouth has to offer?

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth: This highly rated holiday home rental in Portsmouth offers an outdoor pool, a fireplace and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a patio and a garden. Our travellers also rate Historic Old Towne Southern Charm as a favourite home for rent in Portsmouth.

How many holiday rentals are there in Portsmouth?

Choose from 60 Expedia holiday rentals in Portsmouth for a memorable holiday.

What can I see and do in Portsmouth?

Children's Museum of Virginia and Portsmouth Naval Shipyard Museum are a couple of the family-friendly sights, whereas cultural attractions include Commodore Theatre and United States Lightship Portsmouth. Rivers Casino Portsmouth and Virginia Sports Hall of Fame and Museum are other places to visit while you're in town.

What are holiday rentals like in Portsmouth?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portsmouth. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.