Portsmouth vacation rentals

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Booking Insights
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Best Portsmouth vacation rentals

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental - Portsmouth - Balcony
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth, VA
8.9Very good(22)
Apartment
Free Wi-Fi
$206+
Check availability
Cozy 2 Bdrm Cottage King bed - Portsmouth - Kitchen
Cozy 2 Bdrm Cottage King bed
Portsmouth, VA
9.8Wonderful(14)
Cottage
Parking
Free Wi-Fi
Pet friendly
$193+
Check availability
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home - Portsmouth - Bedroom
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth, VA
9.0Wonderful(31)
House
Free Wi-Fi
$337+
Check availability
3 Bedroom near Rivers Casino! - Portsmouth - Dining room
3 Bedroom near Rivers Casino!
Portsmouth, VA
10Wonderful(3)
House
Free Wi-Fi
$280+
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Crown Jewel in the Neighborhood. - Portsmouth - Living room
Crown Jewel in the Neighborhood.
Portsmouth, VA
8.0Very good(7)
House
$311+
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Portsmouth 2br 1ba Getaway - Portsmouth - Kitchen
Portsmouth 2br 1ba Getaway
Portsmouth, VA
7.0Good(3)
House
Free Wi-Fi
$197+
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Cozy Portsmouth Retreat 2br 1ba - Portsmouth - Dining room
Cozy Portsmouth Retreat 2br 1ba
Portsmouth, VA
9.8Wonderful(6)
House
Free Wi-Fi
$204+
Check availability
Private 1 Bed Apt - Historic Olde Towne Portsmouth - Portsmouth - Bedroom
Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth, VA
10Wonderful(2)
Apartment
$203+
Check availability
Modern Portsmouth Apartment Walk to Norfolk Ferry - Portsmouth - Kitchen
Modern Portsmouth Apartment Walk to Norfolk Ferry
Portsmouth, VA
10Wonderful(4)
Apartment
Free Wi-Fi
$219+
Check availability
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino - Portsmouth - Living room
Historic Charm With Modern Comforts & Parking Near Oceanfront and Rivers Casino
Portsmouth, VA
9.6Wonderful(10)
House
Free Wi-Fi
$545+
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Charming 2-Bdrm Gem! Near Casino! - Portsmouth - Building
Charming 2-Bdrm Gem! Near Casino!
Portsmouth, VA
8.3Very good(16)
House
$161+
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Charming 3-Bdrm Gem! Sleeps 6, Near Casino & All - Portsmouth - Living room
Charming 3-Bdrm Gem! Sleeps 6, Near Casino & All
Portsmouth, VA
8.6Very good(12)
House
Free Wi-Fi
$243+
Check availability
Waterfront Townhouse, close to shipyard, hospitals, colleges, beach and shopping - Portsmouth - Living room
Waterfront Townhouse, close to shipyard, hospitals, colleges, beach and shopping
Portsmouth, VA
6.5Okay(17)
House
$216+
Check availability
Family friendly! 3 bd/2 ba, full house, sleeps 8 - Portsmouth - Living room
Family friendly! 3 bd/2 ba, full house, sleeps 8
Portsmouth, VA
10Wonderful(5)
House
Free Wi-Fi
$277+
Check availability
4 Mi to Dtwn Home with Fenced Yard in Portsmouth! - Portsmouth
4 Mi to Dtwn Home with Fenced Yard in Portsmouth!
Portsmouth, VA
3.0Poor(1)
House
Free Wi-Fi
Pool
$288+
Check availability
Waterfront Portsmouth Apt half Mi to Dtwn and Ferry - Portsmouth
Waterfront Portsmouth Apt half Mi to Dtwn and Ferry
Portsmouth, VA
7.9Good(7)
Apartment
Free Wi-Fi
$219+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Portsmouth

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Portsmouth with confidence.

What is the cheapest day of the week to book a vacation rental in Portsmouth?

Sunday offers the lowest rates in Portsmouth, with an average nightly price of $136. The highest prices are found on Friday, with average rates at $341.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

May
June
$227
$307
Cheapest month to stay with an average 65% drop in price.
Most expensive month to stay with an average 43% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Portsmouth vacation rental deals

  • Vacation rentals in Portsmouth are around 38% more expensive than hotels on average. Search here to compare prices for all accommodation types in Portsmouth.
  • The best vacation rental properties in Portsmouth are The Mermaids Porch Bed And Breakfast (9.8, 51 reviews), The Big Brick (9.7, 21), and Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home (9.0, 31), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Portsmouth, you should consider visiting during the low season. The cheapest vacation homes in Portsmouth can be found in May and July.
  • The cheapest night for renting a vacation home in Portsmouth is Sunday. In contrast, the most expensive is Friday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Portsmouth for 6 days.

FAQs when booking a vacation home in Portsmouth

  • What types of vacation rentals are available in Portsmouth?

    There are loads of different property types that you can make your vacation home in Portsmouth. You’ll find agritourism, apartments, cottages and houses.

  • Are there any pet-friendly vacation rentals in Portsmouth?

    There are a number of dog and pet-friendly Portsmouth vacation rentals, with around 2% allowing you to bring your pet along with you.

  • How much is a vacation rental in Portsmouth for tonight?

    In the last 72 hours, users have found Portsmouth vacation rentals for tonight for as low as $250. Search here for similar prices

  • How much is a vacation rental in Portsmouth for this weekend?

    In the last 72 hours, users have found Portsmouth vacation rentals for this weekend for as low as $273 per night. Search here for similar prices

  • How can I find vacation rentals near me in Portsmouth?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Portsmouth?

Our map will help you find the perfect place to stay in Portsmouth by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Portsmouth