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

Holiday Homes in Portsmouth

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Portsmouth holiday homes

A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

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

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.0 out of 10, Very good, (48 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is NZ$611
includes taxes & fees
28 Oct - 29 Oct
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

2. 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, (31 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$495
includes taxes & fees
2 Nov - 3 Nov
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

3. 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$417
includes taxes & fees
22 Oct - 23 Oct
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

4. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
Centrally Located Hampton Roads Home w/ Game Room!
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

5. 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$1,075
includes taxes & fees
26 Oct - 27 Oct
Wooded Wonderland
A room with a pool table, a refrigerator, a staircase, and walls decorated with vinyl records.

6. Cozy 1-bedroom barn in amazing Hampton with cool AC

Cozy 1-bedroom barn in amazing Hampton with cool AC
Hampton
10.0 out of 10, Exceptional, (5 reviews)
The price is NZ$462
includes taxes & fees
22 Oct - 23 Oct
Cozy 1-bedroom barn in amazing Hampton with cool AC
A residential property with a swimming pool, a fenced yard, and a view of a river.

7. Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room

Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room
Deep Creek South
The price is NZ$1,370
includes taxes & fees
3 Nov - 4 Nov
Spacious 4-bedroom townhome in gorgeous Chesapeake with AC and fitness room
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

8. 3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
10.0 out of 10, Exceptional, (56 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is NZ$556
includes taxes & fees
4 Nov - 5 Nov
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

9. 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, (14 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
The price is NZ$575
includes taxes & fees
4 Nov - 5 Nov
Bright 3-bedroom beach house with AC in charming Norfolk
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

10. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.6 out of 10, Exceptional, (23 reviews)
"The property was conveniently located at the beach yet close to Regent University. A great parents’ weekend and graduation getaway spot."
United States
Thomas M.
Beach Bungalow King Bed 1 Floor Living
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

11. Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
Bayview
8.6 out of 10, Excellent, (10 reviews)
"Very Clean, beautiful property situated just blocks from the beach. Neighborhood was very friendly. The entire stay in this charming cottage was delightful!"
United States
Todd C.
The price is NZ$643
includes taxes & fees
2 Nov - 3 Nov
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

12. Charming 3bd - Near beaches - Foosball & Backyard

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (15 reviews)
"The property was great, 5 min walk to the beach. House was bright and cheery with plenty of space for our stay."
United States
Debbie M.
The price is NZ$732
includes taxes & fees
25 Oct - 26 Oct
Charming 3bd - Near beaches - Foosball & Backyard
A modern interior with a staircase leading to a second floor, a living area with a grey sofa, and a kitchen with wooden cabinets.

13. Unique Luxurious Waterfront in Hampton

Unique Luxurious Waterfront in Hampton
Hampton
9.6 out of 10, Exceptional, (4 reviews)
"Great value for the money, great hosts, very renter friendly"
United States
WILLIAM M.
The price is NZ$891
includes taxes & fees
26 Oct - 27 Oct
Unique Luxurious Waterfront in Hampton
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

14. Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.2 out of 10, Wonderful, (7 reviews)
"Very nice place. We enjoyed the fire pit every night and the easy walk to the beach was a plus."
United States
Robin T.
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A view through a window with a grid pattern, overlooking a calm sea and a sandy beach with a small structure and a lifebuoy.

15. Sojourn Aviators Dream on Back River

Sojourn Aviators Dream on Back River
Fox Hill
9.8 out of 10, Exceptional, (32 reviews)
"Great location. Excellent view. The F22 Raptors were cool to see. Not so loud. Host was great. The place does not have a full size oven, so plan accordingly. Beds were comfy."
United States
Jim G.
The price is NZ$806
includes taxes & fees
27 Oct - 28 Oct
Sojourn Aviators Dream on Back River
A wooden gate with a 'Private Property' sign and a 'Security Cameras In Use' sign.

16. 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$665
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-bedroom barn in marvelous Hampton with AC
A waterfront view from a wooden deck with a white railing, a dock extending into the water, and a clear blue sky.

17. Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!
Willoughby Spit
9.0 out of 10, Wonderful, (7 reviews)
The price is NZ$822
includes taxes & fees
1 Nov - 2 Nov
Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portsmouth Hotel Reviews

Schooner Inn

Schooner Inn

8/10 Good
"Good"
Denise 3-night trip
Posted 3 hours ago
Schooner Inn

Find out more about Portsmouth

Portsmouth Holiday Homes information

Number of reviews
198
Accommodation
760 Holiday Homes
Lowest Price
NZ$417
Highest Price
NZ$1,075