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

Portsmouth Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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
9.8 out of 10, Exceptional, (21 reviews)
"As described, clean, comfortable, and convenient! Will look to stay here again next time in the area."
United States
Mark D.
The price is NZ$324
includes taxes & fees
17 Nov - 18 Nov
Private 1 Bed Apt - Historic Olde Towne Portsmouth

2. 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
9.4 out of 10, Exceptional, (10 reviews)
"This was the perfect experience for our vacation and we highly recommend this property and the host was so easy to get in contact with!"
United States
Coachmeech Gaming O.
The price is NZ$454
includes taxes & fees
20 Nov - 21 Nov
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

3. 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, (57 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
The price is NZ$510
includes taxes & fees
18 Nov - 19 Nov
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

4. 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, (29 reviews)
"We really enjoyed our stay! The house was cozy and the perfect size for the three of us. While we didn't do any cooking, the kitchen appeared to have everything you would need. The shower had great hot water, which was nice after a long day. The neighborhood was quiet and peaceful, and there were several good restaurants nearby, making it easy to grab a meal. We'd definitely stay here again!"
United States
Allan S.
The price is NZ$611
includes taxes & fees
15 Nov - 16 Nov
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!

5. 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, (33 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$492
includes taxes & fees
30 Nov - 1 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

6. 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, (13 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$399
includes taxes & fees
16 Nov - 17 Nov
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

7. Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8
Portsmouth
9.4 out of 10, Exceptional, (8 reviews)
"There for a softball Tournament. Close to the highway easy to find"
United States
Ryan H.
Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8

8. 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$1,059
includes taxes & fees
16 Nov - 17 Nov
Wooded Wonderland

9. 3D Theater plus Dock on Small Lake

3D Theater plus Dock on Small Lake
Portsmouth
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Quiet neighborhood with a beautiful lake view."
United States
Muun Queen M.
The price is NZ$695
includes taxes & fees
15 Nov - 16 Nov
3D Theater plus Dock on Small Lake

10. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (119 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is NZ$247
includes taxes & fees
30 Nov - 1 Dec
stayAPT Suites Suffolk-Chesapeake

11. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (42 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
The price is NZ$238
includes taxes & fees
22 Nov - 23 Nov
stayAPT Suites Hampton

12. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (7 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$519
includes taxes & fees
15 Nov - 16 Nov
Guesthouse in ideal location with private entrance

13. Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is NZ$314
includes taxes & fees
13 Dec - 14 Dec
Great Studio | Pool & Hot Tub. Your Next Vacation

14. Sojourn's Harborage | Pet-Friendly

Sojourn's Harborage | Pet-Friendly
East Ocean View
10.0 out of 10, Exceptional, (1 review)
"Beautiful stay. Pet friendly. Spacious. "
United States
Antonio R.
The price is NZ$465
includes taxes & fees
1 Dec - 2 Dec
Sojourn's Harborage | Pet-Friendly

15. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is NZ$339
includes taxes & fees
13 Dec - 14 Dec
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

16. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is NZ$1,169
includes taxes & fees
29 Nov - 30 Nov
Entire Home in Chesapeake, Virginia

17. SEA-clusion 1 cozy apartment across the street from the beach!

SEA-clusion 1 cozy apartment across the street from the beach!
Cottage Line
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed staying here..very cozy..host is amazing"
United States
Theresa S.
The price is NZ$178
includes taxes & fees
15 Nov - 16 Nov
SEA-clusion 1 cozy apartment across the street from the beach!

18. 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$450
includes taxes & fees
30 Nov - 1 Dec
Sojourn's Harborage S

19. The SEA-renity 11 cozy apartment across from the beach

The SEA-renity 11 cozy apartment across from the beach
Cottage Line
The price is NZ$180
includes taxes & fees
7 Dec - 8 Dec
The SEA-renity 11 cozy apartment across from the beach

20. The SEA-renity 12 cozy apartment across from the beach

The SEA-renity 12 cozy apartment across from the beach
Bayview
10.0 out of 10, Exceptional, (1 review)
"Programar con tiempo"
United States
Francisco Javier
The price is NZ$162
includes taxes & fees
15 Nov - 16 Nov
The SEA-renity 12 cozy apartment across from the beach
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.
Save an average of 15% on thousands of hotels when you're signed in

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.

Explore a world of travel with Expedia

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.