Portsmouth vacation rentals

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Top-rated vacation rentals in Portsmouth

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

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Guest favorite

Home in Smithfield

4.97 out of 5 average rating, 203 reviews

Mason Manor - Downtown Smithfield next to WCP

Historic Smithfield 233 S Mason Street 2 Bedrooms 1 Bath Located in the heart of historic Smithfield boasts old world charm and character with a touch of today’s conveniences. The living room has gas fireplace for cool evenings & leads to dining area & updated fully equipped kitchen. The full bath is updated with jetted tub. Front porch swing for relaxing and back deck for entertainment. Windsor Castle Park just steps away. Located just around the corner from restaurants, shopping & more.

Mar 31 – Apr 7

ﺩ.ﺇ426 per night

Guest favorite

Guest suite in Chesapeake

4.97 out of 5 average rating, 235 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!

May 16 – 23

ﺩ.ﺇ316 per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 553 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.

Oct 17 – 24

ﺩ.ﺇ484 per night

Guest favorite

Guest suite in Carrollton

4.98 out of 5 average rating, 160 reviews

2BR 1BA Spacious Guest Suite, Woods & Water Views

NO CLEANING FEES CHARGED! ONLY YOU/YOUR TRAVEL COMPANION ARE GUESTS in the private , in home, upstairs 2 BR 1 BATH UPSTAIRS SUITE W/MINI-KITCHEN. Nothing fancy, but clean, pretty. & relaxingly comfy. Serene, wooded, retreat like setting on a small lake w/wildlife. Centrally located. Visit Williamsburg one day & VA Beach the next. Near Smithfield, universities & military bases. Please read the accommodations policy below before requesting to book. Discount for active military & nurses.

Apr 3 – 10

ﺩ.ﺇ393 per night

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 240 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.

Feb 14 – 21

ﺩ.ﺇ384 per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 477 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.

Sep 20 – 27

ﺩ.ﺇ428 per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 285 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.

Oct 6 – 13

ﺩ.ﺇ505 per night

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.

Jun 8 – 15

ﺩ.ﺇ372 per night

Guest favorite

Guest suite in Norfolk

4.93 out of 5 average rating, 216 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.

Jan 26 – Feb 2

ﺩ.ﺇ465 per night

Guest favorite

Home in Virginia Beach

4.9 out of 5 average rating, 206 reviews

Quilted Quarters by the Bay with Private Entrance

Enjoy beach life, hiking and biking near the Chesapeake Bay in a spacious fully furnished studio with a private entrance and private bath in a very safe and quiet neighborhood with one dedicated parking space as well. Five minute walk to the beach and First Landing State Park with hiking, biking, running trails, locally owned restaurants, bars, shops, breweries, grocery, pharmacy, farmer's market and yoga studio.

Dec 4 – 11

ﺩ.ﺇ327 per night

Guest favorite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 214 reviews

Beautiful and Chic, One Room Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

Feb 4 – 11

ﺩ.ﺇ332 per night

Superhost

Apartment in Portsmouth

4.84 out of 5 average rating, 294 reviews

Spacious 2 bedroom apt in Historic Port Norfolk

If you enjoy homes with lots of history and modern touches, this is the place for you! Our lovely Victorian home was built in the year 1900. We’ve been enjoying all its old world charms since we purchased it in 2016, and we are thrilled to share a part of it with you on your vacations and journeys to exciting new destinations!

Oct 12 – 19

ﺩ.ﺇ384 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Portsmouth vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Portsmouth's top sights

USS Wisconsin BB-6486 locals recommend

Chrysler Museum of Art184 locals recommend

Town Point Park32 locals recommend

Portsmouth City Park8 locals recommend

Waterside District143 locals recommend

Nauticus162 locals recommend

Other great vacation rentals in Portsmouth

Guest favorite

Farm stay in Cape Charles

5.0 out of 5 average rating, 331 reviews

Private Guesthouse on Secluded Waterfront Farm

Oct 4 – 11

ﺩ.ﺇ595 per night

Superhost

Apartment in Portsmouth

4.86 out of 5 average rating, 44 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Jul 7 – 14

ﺩ.ﺇ403 per night

Guest favorite

Apartment in Portsmouth

4.94 out of 5 average rating, 70 reviews

Charming cozy apt historic in Old Towne Portsmouth

Nov 12 – 19

ﺩ.ﺇ507 per night

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 69 reviews

"The Ponderosa B" - Close to the Casino

Dec 17 – 22

ﺩ.ﺇ290 per night

Guest favorite

Apartment in Portsmouth

4.98 out of 5 average rating, 59 reviews

English Basement Hide-Away

Jun 16 – 23

ﺩ.ﺇ434 per night

Guest favorite

Guest suite in Portsmouth

4.94 out of 5 average rating, 36 reviews

Historic Hideaway

Sep 22 – 29

ﺩ.ﺇ436 per night

Guest favorite

Home in Portsmouth

4.87 out of 5 average rating, 31 reviews

Upscale Retreat

Jul 11 – 18

ﺩ.ﺇ433 per night

Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 29 reviews

Entire Apartment - No Cleaning Fees!

Oct 14 – 21

ﺩ.ﺇ362 per night

Show all

Other great vacation rentals in Portsmouth

Superhost

Townhouse in Portsmouth

4.88 out of 5 average rating, 24 reviews

Inviting townhouse featuring 2 full bathrooms

Feb 3 – 10

ﺩ.ﺇ449 per night

Guest favorite

Guest suite in Portsmouth

4.92 out of 5 average rating, 13 reviews

Cozy oasis! VA beach boardwalk is 30 minutes away.

Sep 4 – 11

ﺩ.ﺇ516 per night

Superhost

Apartment in Portsmouth

4.8 out of 5 average rating, 44 reviews

Cozy 2-bedroom unit in Port-Norfolk

Jan 9 – 16

ﺩ.ﺇ328 per night

Guest favorite

Apartment in Portsmouth

4.93 out of 5 average rating, 41 reviews

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

Jul 9 – 16

ﺩ.ﺇ535 per night

Superhost

Home in Portsmouth

4.83 out of 5 average rating, 6 reviews

Cozy Portsmouth Retreat 2BR/1BA

Oct 3 – 10

ﺩ.ﺇ491 per night

Guest favorite

Home in Portsmouth

4.99 out of 5 average rating, 85 reviews

Gorgeous Olde Towne historic home - modern updates

Oct 25 – Nov 1

ﺩ.ﺇ830 per night

Guest favorite

Home in Portsmouth

4.99 out of 5 average rating, 80 reviews

Mid-Century Modern Old Town Portsmouth 3bd/2.5 bth

Sep 23 – 30

ﺩ.ﺇ744 per night

Guest favorite

Guesthouse in Suffolk

4.89 out of 5 average rating, 56 reviews

The Magnolia Guesthouse With A Private Entrance

Nov 24 – Dec 1

ﺩ.ﺇ351 per night

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

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 320 vacation rentals in Highland Park, and over 550 vacation rentals in Olde Towne.
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 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.
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!
Do private suite rentals in Portsmouth have wireless internet?
Absolutely! We offer over 10 private suite rentals with wireless internet in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in townhouse rentals in Portsmouth?
Experience the best of Portsmouth with our townhouse 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 condo rentals in Portsmouth?
Portsmouth has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Portsmouth have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Portsmouth have air conditioning?
Absolutely! We offer over 280 house rentals with air conditioning in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Portsmouth have a gym?
Absolutely! We offer over 20 house rentals with a gym in Portsmouth. Enjoy a tailored experience with all the comforts you desire.

Portsmouth vacation rentals

Top-rated vacation rentals in Portsmouth

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Portsmouth vacation rentals

Stay near Portsmouth's top sights

Other great vacation rentals in Portsmouth

Farm stay in Cape Charles

Apartment in Portsmouth

Apartment in Portsmouth

Apartment in Portsmouth

Apartment in Portsmouth

Guest suite in Portsmouth

Home in Portsmouth

Apartment in Chesapeake

Other great vacation rentals in Portsmouth

Townhouse in Portsmouth

Guest suite in Portsmouth

Apartment in Portsmouth

Apartment in Portsmouth

Home in Portsmouth

Home in Portsmouth

Home in Portsmouth

Guesthouse in Suffolk

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

Where should I stay in Portsmouth?

Are there vacation rentals with a dedicated workspace in Portsmouth?

Are there pet-friendly vacation rentals in Portsmouth?

Are there Portsmouth vacation rentals on Airbnb with pools?

Do private suite rentals in Portsmouth have wireless internet?

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

Are there family-friendly condo rentals in Portsmouth?

Do house rentals in Portsmouth have a bbq area?

Do house rentals in Portsmouth have air conditioning?

Do house rentals in Portsmouth have a gym?

Destinations to explore