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

Holiday Homes in Portsmouth

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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
8.2 out of 10, Very good, (45 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
The price is AU$474
includes taxes & fees
5 Oct - 6 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, (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 AU$444
includes taxes & fees
15 Sept - 16 Sept
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
8.6 out of 10, Excellent, (11 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 AU$312
includes taxes & fees
8 Sept - 9 Sept
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

4. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Little too cold for swimming but the pool was beautiful. House was very clean and comfortable. We had 8 staying and we didn’t feel on top of each other. One of our party left her jewelry behind but the owner was great and arrangements where made to get them back to her. Would definitely stay again!"
United States
Dawn J.
The price is AU$942
includes taxes & fees
7 Sept - 8 Sept
Wooded Wonderland
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.4 out of 10, Exceptional, (9 reviews)
The price is AU$535
includes taxes & fees
9 Sept - 10 Sept
Bright 3-bedroom beach house with AC in charming Norfolk
A modern dining area with a glass table, blue upholstered chair, and black chairs.

6. Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (36 reviews)
"Great little house beach was good for small kids first trip to beach"
United States
Layton H.
The price is AU$606
includes taxes & fees
7 Sept - 8 Sept
Sojourn | Coastal Cottage | 3 BR
A beach at sunset with a building in the background.

7. Cozy Beach Home in Oceanview

Cozy Beach Home in Oceanview
Bayview
9.8 out of 10, Exceptional, (47 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is AU$496
includes taxes & fees
17 Sept - 18 Sept
Cozy Beach Home in Oceanview
A modern kitchen with white cabinets, a wooden dining table, and a blue accent wall.

8. Beach Bungalow King Bed 1 Floor Living

Beach Bungalow King Bed 1 Floor Living
Bayview
9.6 out of 10, Exceptional, (22 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.
The price is AU$654
includes taxes & fees
8 Sept - 9 Sept
Beach Bungalow King Bed 1 Floor Living
A narrow hallway with a white door, a bench, and a row of wooden stools.

9. Boho beach house w/foosball & patio

Boho beach house w/foosball & patio
Willoughby Spit
9.4 out of 10, Exceptional, (3 reviews)
"Extremely clean and family friendly. Easy access to the beach. Located in a quiet neighborhood"
United States
Mara
The price is AU$735
includes taxes & fees
14 Sept - 15 Sept
Boho beach house w/foosball & patio
A modern kitchen with white cabinets, stainless steel appliances, and a large island with bar stools.

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

Charming 3bd - Near beaches - Foosball & Backyard
Bayview
9.6 out of 10, Exceptional, (12 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.
Charming 3bd - Near beaches - Foosball & Backyard
A spacious living room with a white sofa, a teal sectional, and a patterned rug.

11. Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard
Bayview
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful home that is very close to the ocean with lots of options of things to do. We had a wonderful stay!"
United States
Nate K.
The price is AU$828
includes taxes & fees
21 Sept - 22 Sept
Pet Friendly Family Getaway + 1 Block from Beach + Game Room + Fenced Yard

12. Beautiful, spacious home in welcoming Norfolk.

Beautiful, spacious home in welcoming Norfolk.
Norfolk
7.4 out of 10, Good, (3 reviews)
"Host was great, very responsive. The house was great and very clean. Very quiet neighborhood. Short drive to everything Norfolk and Virginia Beach had to offer."
United States
shereece t.
The price is AU$852
includes taxes & fees
17 Sept - 18 Sept
Beautiful, spacious home in welcoming Norfolk.
A beach with a wooden boardwalk, sand dunes, and the ocean in the background.

13. 3 bedroom home by the Sea, a block from the beach!

3 bedroom home by the Sea, a block from the beach!
Bayview
10.0 out of 10, Exceptional, (1 review)
"Fantastic home and host! Neighboring also came out welcome us and offer info about the area! Comfy bed and sofa too! Beach was super close!"
United States
Becky G.
The price is AU$573
includes taxes & fees
29 Sept - 30 Sept
3 bedroom home by the Sea, a block from the beach!
A covered porch with a hanging chair, a small table, and a view of a snowy yard.

14. 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, (54 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
The price is AU$452
includes taxes & fees
15 Sept - 16 Sept
3-bedroom home away from home in fabulous Chesapeake, Virginia.
A sunlit room with a ceiling fan, two wicker chairs with cushions, a striped rug, and a small table with a plant.

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

Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
Cottage Park
9.0 out of 10, Wonderful, (6 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.
The price is AU$644
includes taxes & fees
15 Sept - 16 Sept
Cozy 3BD Beachfront - Foosball & Yard Games w/ BBQ
A kitchen with a wooden island, bar stools, a ceiling fan, and a refrigerator.

16. 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, (4 reviews)
"Walking distance to a very calm and not crowded beach. Clean and well furnished cottage with new bathroom fixtures and kitchen appliances. Plenty of towels, linens, soap and shampoo, and paper goods. Would appreciate a bit more drawer space for clothes. Nice to have the covered outdoor space for all our wet and sandy beach stuff but not the most welcoming spot for outdoor dining. Owner communication was responsive and check in process was a breeze. I highly recommend this cozy cottage!"
United States
Virginia L.
The price is AU$500
includes taxes & fees
29 Sept - 30 Sept
Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly
A room with a dining table and chairs, a door, a radiator, and a refrigerator.

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

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
The price is AU$283
includes taxes & fees
25 Sept - 26 Sept
Cozy 1-bedroom barn in marvelous Hampton with AC
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dishwasher.

18. 2 Minutes Walk to the BEACH

2 Minutes Walk to the BEACH
East Ocean View
10.0 out of 10, Exceptional, (1 review)
"Convenient location. Nice big rooms and great bathrooms. A lot of room to gather with open concept 1st floor. I would recommend this property."
United States
Lisa A.
The price is AU$1,155
includes taxes & fees
11 Sept - 12 Sept
2 Minutes Walk to the BEACH

19. Hot Tub | 9 beds | Fenced Yard

Hot Tub | 9 beds | Fenced Yard
Downtown Hampton
4.8 out of 10, (8 reviews)
"Convenient location and plenty of space, but the house is in clear disrepair. We were in town to see our daughter graduate from Hampton University, and the location was ideal for the ceremony."
United States
Kristin J.
The price is AU$755
includes taxes & fees
16 Sept - 17 Sept
Hot Tub | 9 beds | Fenced Yard
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

Hampton Inn Virginia Beach-Oceanfront South

Hampton Inn Virginia Beach-Oceanfront South

10/10 Excellent
"The room was clean. The hotel accommodates pets so you will see dogs during your stay. It has quick access to the beach and the boardwalk and a restaurant for affordable eats. This is the south version of the Hampton Inn hotel, so make sure to take note of the address before traveling. I made the mistake of going to the north Hampton inn hotel first."
Shafa 3-night trip
Posted 3 hours ago
Hampton Inn Virginia Beach-Oceanfront South

Find out more about Portsmouth

Portsmouth Holiday Homes information

Number of reviews
244
Accommodation
787 Holiday Homes
Lowest Price
AU$283
Highest Price
AU$1,155