Vacation rentals in Portsmouth

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Top-rated vacation rentals in Portsmouth

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

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Guest favourite

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. 23 – 30

$183 CAD per night

Guest favourite

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. 25 – Sep. 1

$221 CAD per night

Guest favourite

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!

Jul. 21 – 28

$204 CAD per night

Guest favourite

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

$221 CAD per night

Guest favourite

Guest suite in Carrollton

4.98 out of 5 average rating, 162 reviews

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

NO CLEANING FEES! ONLY YOU/YOUR TRAVEL COMPANION ARE GUESTS in the private, in home, upstairs 2 BR 1 BATH GUEST SUITE W/MINI-KITCHEN. 1 guest per bedroom, ONLY (see “ACCOMMODATIONS POLICY” below). 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, Newport News, universities & military bases. Discount for active military & nurses.

Jan. 19 – 26

$173 CAD per night

Guest favourite

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. 30 – Dec. 7

$175 CAD per night

Guest favourite

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.

Mar. 17 – 24

$194 CAD per night

Guest favourite

Townhouse in Chesapeake

4.88 out of 5 average rating, 110 reviews

2BR-1.5 Bath Electric & Vibrant R&R Townhome

Listing description Kick back & relax in this calm, stylish space. 1600 sq ft stunning renovated & designed townhome! -Skip the traffic; 15 min drive to most of Hampton Roads, beaches; 3 mins from restaurants, groceries & more -Free parking -Optimal cleaning 100% disinfected space -2 bedrooms -Comfortable 2 Queen Beds & 1 Full Futon -1.5 baths with high end, modern finishes -Outdoor back private patio seating - Smart home features: keyless access cord + living room TV with roku

Aug. 9 – 16

$309 CAD per night

Guest favourite

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.

Sep. 25 – Oct. 2

$229 CAD per night

Guest favourite

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. 13 – 20

$186 CAD per night

Guest favourite

Guest suite in Norfolk

4.93 out of 5 average rating, 218 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. 28 – Feb. 4

$223 CAD per night

Guest favourite

Guesthouse in Chesapeake

4.98 out of 5 average rating, 216 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.

Jan. 31 – Feb. 7

$152 CAD per night