Vacation rentals in Portsmouth

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Top-rated vacation rentals in Portsmouth

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Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 236 reviews

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!

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 556 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Guest favorite

Guest suite in Portsmouth

4.94 out of 5 average rating, 17 reviews

Cozy oasis! VA beach boardwalk is 30 minutes away.

Relax with family and friend at this peaceful upstairs Loft. 3pm 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 nice Loft.

Guest favorite

Guest suite in Portsmouth

4.95 out of 5 average rating, 37 reviews

Historic Hideaway

You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

Guest favorite

Apartment in Portsmouth

4.88 out of 5 average rating, 48 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Enjoy easy access to everything from this perfectly located, fully furnished home. Walk to fine dining, museums, a historic theater. Visit the waterfront where you can view the Navy ships or ride the Ferry to Norfolk to experience Waterside & MacArthur Mall. This is a great place for traveling professionals or those in town for sightseeing or local events. Virginia Beach Oceanfront is 30 minutes away. Home is located in a beautiful, historic area and only 8 minutes from the new casino!

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 72 reviews

"The Ponderosa B" - Close to the Casino

Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice family oriented neighborhood about 1/2 mile Rivers Casino! Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign and cones for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth Areana area and 5.9 miles to Downtown Norfolk, 22 miles to VB Oceanfront.

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 242 reviews

Cozy Ground Floor Apt in Historic Home

Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 482 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Guest favorite

Apartment in Portsmouth

4.98 out of 5 average rating, 60 reviews

English Basement Hide-Away

Private Suite in the heart of Olde Towne, Portsmouth! This historic English Basement style home has a private street entrance. Walking distance from the the waterfront, restaurants, local shopping, Coast Guard Base and Navy Hospital, Atlantic Union Bank Pavillion, ferry into Downtown Norfolk, The Norva, and the Tides Stadium. 9 minute drive to the Rivers Casino. Quick drive to Military Bases, and approx. a 20 minute drive to VA Beach and a 45 minute drive to Williamsburg/Busch Gardens.

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 289 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. (Please also check out our additional property "The Water's Edge"). Sun, Se and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house is located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High speed fiber-optic wifi and cable with blue ray player provided.

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 106 reviews

Best location in Olde Towne Portsmouth

This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.

Guest favorite

Guest suite in Norfolk

4.93 out of 5 average rating, 220 reviews

Cobblestone street apartment with rooftop views!

Historic, Downtown area of Norfolk. Walking distance to shops, restaurants, museums, landmarks, parks, memorials, EVMS, & CHKD. This special residence is on the National Register of Historic Homes, includes a clawfoot tub & rooftop patio (no hold harm). This High Victorian Italian home was built in 1870, with a Mansard roof & features an ornamental cast iron veranda. John Cary Weston built this as a summer residence following the Civil War.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Portsmouth vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Portsmouth's top sights

USS Wisconsin BB-6486 locals recommend

Town Point Park32 locals recommend

Chrysler Museum of Art184 locals recommend

Portsmouth City Park8 locals recommend

Waterside District143 locals recommend

Old Dominion University26 locals recommend

Other great vacation rentals in Portsmouth

Guest favorite

Home in Portsmouth

4.97 out of 5 average rating, 38 reviews

Penny’s Palace 1 Bed/1 Bath Home

Guest favorite

Home in Portsmouth

4.92 out of 5 average rating, 39 reviews

Hidden Gem

Guest favorite

Apartment in Portsmouth

4.89 out of 5 average rating, 63 reviews

Old world charm

Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 32 reviews

Entire Apartment - No Cleaning Fees!

Superhost

Home in Portsmouth

4.86 out of 5 average rating, 7 reviews

Cozy Portsmouth Retreat 2BR/1BA

Guest favorite

Apartment in Suffolk

5.0 out of 5 average rating, 70 reviews

Country Living Guest House (Upstairs/Downstairs)

Guest favorite

Apartment in Portsmouth

4.93 out of 5 average rating, 42 reviews

Comfortable, Two Bedroom, One bath, King bed, Home

Guest favorite

Guest suite in Chesapeake

4.92 out of 5 average rating, 48 reviews

Guest Suite with Private entrance & bathroom

Show all

Quick stats about vacation rentals in Portsmouth

Total rentals
580 properties
Rentals with dedicated workspaces
350 properties have a dedicated workspace
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
210 properties allow pets
Family-friendly rentals
310 properties are a good fit for families
Total number of reviews
17K reviews

Frequently Asked Questions

Do guesthouse rentals in Portsmouth have wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Portsmouth?
Experience the best of Portsmouth with our guesthouse rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Portsmouth?
Portsmouth has more than 310 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Portsmouth?
Yes! Work meets play with ease at over 350 vacation rentals in Portsmouth featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Portsmouth vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Portsmouth, available on Airbnb. Make a splash and soak up the sun in style!
Are there pet-friendly vacation rentals in Portsmouth?
Four-legged friends are welcome in Portsmouth. Choose from more than 210 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Portsmouth?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a gym, over 40 homes with a bbq area, over 280 homes with air conditioning, over 280 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Portsmouth have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Portsmouth?
Make yourself at home in Portsmouth by choosing from our most frequently booked neighborhoods. We have over 320 vacation rentals in Ghent, over 550 vacation rentals in Olde Towne, and over 320 vacation rentals in Highland Park.
Do private suite rentals in Portsmouth have air conditioning?
Absolutely! We offer over 10 private suite rentals with air conditioning in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Portsmouth

Top-rated vacation rentals in Portsmouth

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Portsmouth vacation rentals

Stay near Portsmouth's top sights

Other great vacation rentals in Portsmouth

Home in Portsmouth

Home in Portsmouth

Apartment in Portsmouth

Apartment in Chesapeake

Home in Portsmouth

Apartment in Suffolk

Apartment in Portsmouth

Guest suite in Chesapeake

Quick stats about vacation rentals in Portsmouth

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do guesthouse rentals in Portsmouth have wireless internet?

How much does it cost to stay in guesthouse rentals in Portsmouth?

Are there family-friendly vacation rentals in Portsmouth?

Are there vacation rentals with a dedicated workspace in Portsmouth?

Are there Portsmouth vacation rentals on Airbnb with pools?

Are there pet-friendly vacation rentals in Portsmouth?

What are the most popular amenities for House Rentals in Portsmouth?

Do house rentals in Portsmouth have a bbq area?

Where should I stay in Portsmouth?

Do private suite rentals in Portsmouth have air conditioning?

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