Portsmouth Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Portsmouth vacation rentals

A narrow brick pathway flanked by two houses with siding.

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.
$147 nightly
The price is $172
Nov 16 - Nov 17
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A living room with a glass coffee table, two leather chairs, a desk, and a green door.

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.
$217 nightly
The price is $253
Nov 20 - Nov 21
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

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.
$244 nightly
The price is $284
Nov 17 - Nov 18
Total with taxes and fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A small house with a red door, a window with blinds, a wooden table and chairs, a black lamp, and a striped rug.

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.
$295 nightly
The price is $342
Nov 16 - Nov 17
Total with taxes and fees
Cozy Private Cottage, Wifi, Pet Friendly & Perfect for Extended Stays!
A modern kitchen with grey cabinets, a stainless steel microwave, a built-in oven, and a granite countertop.

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.
$234 nightly
The price is $272
Nov 30 - Dec 1
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A poolside area with a covered seating area, a pool, and a white fence.

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
$205 nightly
The price is $239
Dec 1 - Dec 2
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A dining area with a dark wooden table and chairs, a vase with white flowers, and a wall-mounted picture.

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.
$249 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Walkable to the Casino and Family friendly! 3 bd/2 ba, full house, sleeps 8
A residential property with a swimming pool, a covered patio, and a detached garage.

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.
$509 nightly
The price is $588
Nov 16 - Nov 17
Total with taxes and fees
Wooded Wonderland
A wooden deck with a railing overlooking a lake, surrounded by lush greenery.

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.
$340 nightly
The price is $393
Nov 16 - Nov 17
Total with taxes and fees
3D Theater plus Dock on Small Lake
Room

10. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (119 reviews)
"Room was clean, very nice and quiet property. Loved staying here and will recommend anyone who visits the area"
United States
olivia
$119 nightly
The price is $137
Nov 23 - Nov 24
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
Interior

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
$108 nightly
The price is $127
Nov 23 - Nov 24
Total with taxes and fees
stayAPT Suites Hampton
A kitchen with white cabinets, a stainless steel sink, a granite countertop, a stove, and a coffee maker.

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.
$253 nightly
The price is $289
Nov 16 - Nov 17
Total with taxes and fees
Guesthouse in ideal location with private entrance
An outdoor patio with stone walls, a round table, and green chairs.

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.
$150 nightly
The price is $173
Dec 3 - Dec 4
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation
An outdoor patio with wooden furniture, a fire pit, and a covered area with a view of the surrounding landscape.

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.
$245 nightly
The price is $261
Dec 1 - Dec 2
Total with taxes and fees
Sojourn's Harborage | Pet-Friendly
An outdoor patio with stone walls, a round table, and green chairs.

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.
$163 nightly
The price is $188
Dec 3 - Dec 4
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
A staircase with a wooden handrail and white balusters, carpeted steps, and a white door with a stained glass window.

16. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
$552 nightly
The price is $637
Nov 29 - Nov 30
Total with taxes and fees
Entire Home in Chesapeake, Virginia
A beach with waves, a clear sky, and a distant pier.

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.
$87 nightly
The price is $99
Nov 16 - Nov 17
Total with taxes and fees
SEA-clusion 1 cozy apartment across the street from the beach!
An outdoor patio with wooden furniture, a fire pit, and a covered area with a view of the surrounding landscape.

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
$235 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
Sojourn's Harborage S
A sandy beach with a wooden fence, grassy dunes, and a clear blue sky.

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

The SEA-renity 11 cozy apartment across from the beach
Cottage Line
$88 nightly
The price is $100
Dec 7 - Dec 8
Total with taxes and fees
The SEA-renity 11 cozy apartment across from the beach
A sandy beach with footprints, a clear blue sky, and a distant pier.

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
$79 nightly
The price is $89
Nov 16 - Nov 17
Total with taxes and fees
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.
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Top Portsmouth Hotel Reviews

A spacious room with a pool table, comfortable seating, and large windows offering a view of the cityscape.
Renaissance Portsmouth-Norfolk Waterfront Hotel

Renaissance Portsmouth-Norfolk Waterfront Hotel

Renaissance Portsmouth-Norfolk Waterfront Hotel
Portsmouth

10/10 Excellent

Clean, safe, friendly staff, Beautiful view of the Harbor...had a great time...
United States
Christina
Reviewed April 20, 2025
Renaissance Portsmouth-Norfolk Waterfront Hotel

Find out more about Portsmouth

Everything you need to know about Portsmouth vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portsmouth vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portsmouth vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Portsmouth vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portsmouth. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Portsmouth in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $89 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Portsmouth rentals

At Expedia, we put the best Portsmouth vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Portsmouth rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portsmouth vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portsmouth. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Portsmouth?

Yes, there are vacation rentals in Portsmouth near Children's Museum of Virginia, or you can go with a more remote option if you want a relaxing stay. Visitors like the top-notch restaurants and museums in Portsmouth. Make sure you allow time to enjoy the riverfront during your vacation.

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

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth: Visitors give good reviews to this Portsmouth vacation home rental, which 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 travelers also rate Historic Old Towne Southern Charm as a favorite home for rent in Portsmouth.

How many vacation rentals are there in Portsmouth?

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

What can I see and do in Portsmouth?

Children's Museum of Virginia and Portsmouth Naval Shipyard Museum are a couple of 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 vacation rentals like in Portsmouth?

Vacation rentals are private accommodations you can reserve for several days or more in Portsmouth. Vacation rentals offer extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

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