Holiday rentals in Portsmouth

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Top-rated holiday rentals in Portsmouth

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Guest suite in Portsmouth
Cozy oasis for a great getaway!
Relax with the whole family at this peaceful upstairs Loft. 2pm check in💪Located in the heart of Portsmouth with lots of memorable activities to attend to. Very quiet neighborhood for traveling guess to relax, stretch and sleep. Interesting in enjoying a night out? We have rivers casino that’s 5 mins away, or you can ride the tide down to waterside and enjoy a friendly day out eating at affordable tasty restaurants. Our children’s museum is only 7 mins away! Don’t wait to book this snuggly Loft.
27 Oct – 3 Nov
$81 SGD per night
5.0 out of 5 average rating, 6 reviews
Guest favourite
Apartment in Portsmouth
‘Captains Corner’ 1 Bedrm CONDO Historic Old Towne
Historic DOWNTOWN with a ‘nautical flare’! 900 sq. ft. 1 BR. This charming unit boasts a compact fully equipted kitchen. OPEN FLOOR PLAN! 65” TV offering WiFi, streaming and basic cable! Walk to fine dining, museums, theater and shopping! 6 blocks to a vibrant “WATERFRONT”. Ferry Service to Norfolk. An old historic building that includes 3 condominiums with free street parking, and additional 24/7 parking in rear. 25 STAIRS One Flight Up. Suitable for 1 or 2 guests NO ENTERTAINING. NO PETS!!
1–8 Apr
$120 SGD per night
4.96 out of 5 average rating, 81 reviews
Guest favourite
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!
29 Jul – 5 Aug
$156 SGD per night
4.97 out of 5 average rating, 224 reviews

Popular amenities for Portsmouth holiday rentals

Stay near Portsmouth's top sights

USS Wisconsin BB-6486 locals recommend
Chrysler Museum of Art184 locals recommend
Waterside District143 locals recommend
Town Point Park32 locals recommend
Portsmouth City Park8 locals recommend
Nauticus162 locals recommend

Other great holiday rentals in Portsmouth

Guest favourite
Home in Portsmouth
Mid-Century Modern Old Town Portsmouth 3bd/2.5 bth
11–18 Jan
$230 SGD per night
4.99 out of 5 average rating, 80 reviews
Guest favourite
Flat in Portsmouth
New casino nearby! King Bed, Two Bdrm, 1 1/2 Bth
27 May – 3 Jun
$152 SGD per night
4.91 out of 5 average rating, 43 reviews
Guest favourite
Home in Portsmouth
Penny’s Palace 1 Bed/1 Bath Home
9–16 Jun
$127 SGD per night
4.96 out of 5 average rating, 24 reviews
Guest favourite
Home in Portsmouth
Gorgeous Olde Towne historic home - modern updates
24–31 Dec
$259 SGD per night
4.99 out of 5 average rating, 81 reviews
Guest favourite
Guest suite in Portsmouth
Historic Hideaway
19–26 Jan
$134 SGD per night
4.94 out of 5 average rating, 33 reviews
Guest favourite
Home in Portsmouth
Waters Edge Retreat!
14–21 Apr
$385 SGD per night
5.0 out of 5 average rating, 49 reviews
Superhost
Flat in Portsmouth
Private 1 Bed Apt - Historic Olde Towne Portsmouth
26 Mar – 2 Apr
$121 SGD per night
4.85 out of 5 average rating, 40 reviews
Guest favourite
Home in Portsmouth
Wooded Wonderland
18–25 Jan
$242 SGD per night
4.92 out of 5 average rating, 50 reviews
Guest favourite
Guest house in Suffolk
The Magnolia Guesthouse With A Private Entrance
12–19 Feb
$104 SGD per night
4.92 out of 5 average rating, 49 reviews
Guest favourite
Home in Portsmouth
Hidden Gem
13–20 May
$138 SGD per night
4.91 out of 5 average rating, 33 reviews
Superhost
Townhouse in Portsmouth
Inviting townhouse featuring 2 full bathrooms
2–9 Sep
$145 SGD per night
4.86 out of 5 average rating, 21 reviews
Guest favourite
Home in Portsmouth
YES Queen! The Bridgerton House
29 Apr – 6 May
$455 SGD per night
5.0 out of 5 average rating, 7 reviews

Quick stats about holiday rentals in Portsmouth

Total rentals

610 properties

Rentals with dedicated workspaces

380 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

220 properties allow pets

Family-friendly rentals

320 properties are a good fit for families

Total number of reviews

17K reviews

Destinations to explore

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  2. United States
  3. Virginia
  4. Portsmouth