
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.
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Holiday rentals for every style
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Popular amenities for Portsmouth holiday rentals
Other great holiday rentals in Portsmouth

Flat in Olde Towne
4.83 out of 5 average rating, 107 reviewsPrivate 1 Bed Apt - Historic Olde Towne Portsmouth
Superhost

Home in Port Norfolk
4.69 out of 5 average rating, 161 reviewsCozy Modern Cabin
Guest favourite

Home in Olde Towne
4.96 out of 5 average rating, 28 reviewsTudor Treasure in Olde Towne
Superhost

Guest suite in Chesapeake
4.94 out of 5 average rating, 33 reviewsStudio apartment
Guest favourite

Home in Portsmouth
5 out of 5 average rating, 9 reviewsComfortable Portsmouth Classic
Superhost

Home in Portsmouth
4.84 out of 5 average rating, 37 reviewsElegance Escape on Saunders Dr
Guest favourite

Guest suite in Portsmouth
4.86 out of 5 average rating, 72 reviewsPrivate second floor apt 5 min from Rivers casino.
Top guest favourite

Private room in Ghent
4.98 out of 5 average rating, 310 reviewsThe Owl Room in Late 1800s Historic House
Quick stats about holiday rentals in Portsmouth
Total rentals
500 properties
Total number of reviews
18K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Destinations to explore
- Virginia Beach Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Ocean City Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Apartment rentals Portsmouth
- Rentals with a washing machine and dryer Portsmouth
- Waterfront rentals Portsmouth
- Pet-friendly rentals Portsmouth
- Rentals with a patio Portsmouth
- Rentals with lake access Portsmouth
- Rentals with outdoor seating Portsmouth
- Rentals with a firepit Portsmouth
- Rentals with a fireplace Portsmouth
- Rentals with beach access Portsmouth
- Fitness-friendly rentals Portsmouth
- House rentals Portsmouth
- Rentals with pools Portsmouth
- Rentals with an EV charger Portsmouth
- Rentals with a kayak Portsmouth
- Flat rentals Portsmouth
- Family-friendly rentals Portsmouth
- Family-friendly rentals Portsmouth
- Rentals with breakfast Portsmouth
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Corolla Beach
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Kingsmill Resort
- Outlook Beach
- Haven Beach
- Jamestown Settlement
- Ocean Breeze Waterpark
- Currituck Beach Lighthouse
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Kiptopeke Beach
- Wilkins Beach
- Little Creek Beach
- Golden Horseshoe Golf Club