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, 205 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.

Dec 17 – 24

$99 per night

Guest favorite

Guest suite in Hampton

4.96 out of 5 average rating, 467 reviews

Storybook Cottage

Beautiful studio within walking distance to downtown Hampton waterfront, marinas, shopping, dining, microbreweries, arts & museum district. Short drive to beaches, NASA/Langley AFB, Hampton U., and Ft. Monroe. Centrally located off I-64 between Williamsburg and Va. Beach. Quiet and cozy. Has private front and rear entrances and covered private back porch. Perfect for couples & business travelers. Complimentary coffee, tea , water, etc. No 3rd party reservations. Self check in after 3 pm.

Aug 27 – Sep 3

$117 per night

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!

Oct 2 – 9

$114 per night

Guest favorite

Guesthouse in Norfolk

4.98 out of 5 average rating, 554 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.

Dec 14 – 21

$112 per night

Guest favorite

Guest suite in Portsmouth

4.94 out of 5 average rating, 36 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!

Jan 14 – 21

$100 per night

Guest favorite

Apartment in Portsmouth

4.87 out of 5 average rating, 47 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!

Jun 29 – Jul 6

$99 per night

Guest favorite

Apartment in Portsmouth

4.96 out of 5 average rating, 241 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.

Nov 7 – 14

$89 per night

Guest favorite

Guest suite in Chesapeake

4.95 out of 5 average rating, 479 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.

Feb 25 – Mar 4

$99 per night

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.

Jul 13 – 20

$102 per night

Guest favorite

Guesthouse in Hampton

4.99 out of 5 average rating, 288 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 16 – 23

$117 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.

Sep 23 – 30

$90 per night

Guest favorite

Apartment in Portsmouth

4.93 out of 5 average rating, 73 reviews

Charming cozy apt historic in Old Towne Portsmouth

Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick 5 minute walk and every Saturday morning the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. Let us make your stay stress free and enjoyable.

Jun 11 – 18

$105 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

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

Apartment in Portsmouth

4.89 out of 5 average rating, 37 reviews

"The Ponderosa A" - Close to the Casino

Oct 6 – 11

$79 per night

Guest favorite

Apartment in Portsmouth

4.89 out of 5 average rating, 62 reviews

Old world charm

Aug 24 – 31

$88 per night

Superhost

Home in Portsmouth

4.92 out of 5 average rating, 26 reviews

Comfortable & Private 2 Bedrm Cottage w/ King bed.

May 9 – 16

$105 per night

Guest favorite

Home in Portsmouth

4.92 out of 5 average rating, 39 reviews

Hidden Gem

Jul 24 – 31

$97 per night

Guest favorite

Home in Portsmouth

4.97 out of 5 average rating, 37 reviews

Penny’s Palace 1 Bed/1 Bath Home

Aug 23 – 30

$106 per night

Guest favorite

Guest suite in Portsmouth

4.93 out of 5 average rating, 14 reviews

Cozy oasis! VA beach boardwalk is 30 minutes away.

Aug 6 – 13

$120 per night

Superhost

Townhouse in Portsmouth

4.96 out of 5 average rating, 24 reviews

Inviting townhouse featuring 2 full bathrooms

Oct 23 – 30

$113 per night

Guest favorite

Apartment in Chesapeake

5.0 out of 5 average rating, 31 reviews

Entire Apartment - No Cleaning Fees!

Mar 15 – 22

$106 per night

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Other great vacation rentals in Portsmouth

Guest favorite

Home in Norfolk

4.92 out of 5 average rating, 155 reviews

@Whit’s End? Come in and Relax

Oct 12 – 19

$75 per night

Guest favorite

Guest suite in Virginia Beach

4.92 out of 5 average rating, 237 reviews

Cozy Private Studio

Sep 27 – Oct 4

$84 per night

Guest favorite

Apartment in Hampton

4.97 out of 5 average rating, 127 reviews

Downtown Hampton's Hidden Gem with Queen Bed

May 18 – 25

$107 per night

Superhost

Tiny home in Chesapeake

4.84 out of 5 average rating, 128 reviews

Rural Tiny House in the Edge Of the Woods

Sep 2 – 9

$126 per night

Guest favorite

Townhouse in Chesapeake

4.9 out of 5 average rating, 103 reviews

Family friendly townhouse

Oct 5 – 12

$127 per night

Guest favorite

Guest suite in Virginia Beach

4.85 out of 5 average rating, 356 reviews

Guest Suite Studio w/ Kitchenette & Private bath.

Jun 13 – 20

$133 per night

Superhost

Condo in Norfolk

4.79 out of 5 average rating, 155 reviews

Best Value Condo in Downtown Norfolk

Jul 28 – Aug 4

$140 per night

Guest favorite

Place to stay in Virginia Beach

4.99 out of 5 average rating, 116 reviews

Salty Willow-a “suite retreat” in the heart of VB!

Nov 12 – 19

$109 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 Highland Park, over 320 vacation rentals in Ghent, 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 apartment rentals in Portsmouth?
Experience the best of Portsmouth with our apartment rentals, starting at about $20 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 house rentals in Portsmouth?
Portsmouth has more than 160 family-friendly house 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 40 house rentals with a bbq area in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Portsmouth have air conditioning?
Absolutely! We offer over 10 townhouse rentals with air conditioning in Portsmouth. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Portsmouth have a gym?
Absolutely! We offer over 30 apartment 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

Apartment in Portsmouth

Apartment in Portsmouth

Home in Portsmouth

Home in Portsmouth

Home in Portsmouth

Guest suite in Portsmouth

Townhouse in Portsmouth

Apartment in Chesapeake

Other great vacation rentals in Portsmouth

Home in Norfolk

Guest suite in Virginia Beach

Apartment in Hampton

Tiny home in Chesapeake

Townhouse in Chesapeake

Guest suite in Virginia Beach

Condo in Norfolk

Place to stay in Virginia Beach

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 apartment rentals in Portsmouth?

Are there family-friendly house rentals in Portsmouth?

Do house rentals in Portsmouth have a bbq area?

Do townhouse rentals in Portsmouth have air conditioning?

Do apartment rentals in Portsmouth have a gym?

Destinations to explore