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House vacation rentals in Portsmouth

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Top-rated house rentals in Portsmouth

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Home in Williamsburg

4.85 out of 5 average rating, 213 reviews

Colonial Retreat

Enjoy a getaway in our 1940 Cape Cod home minutes from Colonial Williamsburg & Jamestown. Within biking distance to many attractions such as Williamsburg Winery, Jamestown Island & Settlement, Jamestown Beach, and Billsburg Brewery. Busch Gardens & Water Country are a 15 minute drive. The house was refinished in 2021; you'll find an updated kitchen, smart TVs, large back patio & front porch. Please read the house rules before booking. No smoking. Need more space? Inquire about our other units

Home in Smithfield

4.96 out of 5 average rating, 246 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.

Home in Portsmouth

4.96 out of 5 average rating, 105 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

“The Captains Cottage” offers a quiet private RIVERFRONT setting. Bring kayaks, paddle board, fish or just sit and bird watch! Enjoy the sunset at this 1500 sq. ft. quaint and cozy 2 story cottage. Hampton Roads has so much to offer, and the Portsmouth area is no exception! There’s a ‘historic downtown’ and a vibrant waterfront only 4 miles from the captains cottage! Need a break from the river? Virginia Beach OCEANFRONT is 30 minutes away! 6 guest limit. Guests of the 2 legged variety.

Home in Portsmouth

4.83 out of 5 average rating, 110 reviews

Fun 3BR-2bath with a game room-Near Rivers Casino

Escape to this entertaining 3BR, 2-bath retreat in Portsmouth, VA. Just 4 mins from Rivers Casino and 15 mins from Waterside District. A 30-min drive takes you to VA Beach, ODU, NSU, HU, and CNU. Stay connected with WiFi & Smart TVs. The outdoor space is a treat with a grill & various activities. Indoors, there's a pool table, darts, table tennis, and board games. The renovated kitchen has stainless steel appliances. This home offers a wide range of amenities for a memorable getaway.

Home in Norfolk

4.8 out of 5 average rating, 114 reviews

Poseidon - Beach-Front with Fireplace

Unique & gorgeous beachfront rental. This area was a gathering spot for rowdy commercial sailing captains that moved goods between Norfolk & Baltimore & an alleged meeting spot for Rum Runners in the 1920's. Includes wood floors, sailing inspired sconces, large pantry and fireplace. Beautiful wood trim & wainscoting created by craftsmen that trimmed ship interiors over a century ago, beach-front windows, large open kitchen, dishwasher, microwave oven, shared sauna, & washer/dryer

Home in East Ocean View

4.86 out of 5 average rating, 119 reviews

☼ Coastal Cottage- 5 min walk to beach | parking ☼

Enjoy close proximity to all the best attractions the area has to offer, or simply bum it on the beach while snagging a local cup of coffee or craft beer - all within a few steps! A wonderful location for a beach getaway with friends or family. -5 min walk to the beach -8 min walk to a local coffee shop/brewery -25 min drive to Virginia Beach/boardwalk area -10 min drive to Norfolk Botanical Garden -20 min drive to the Zoo -10 min drive to Ikea / Norfolk Premium Outlets

Home in Gloucester Point

4.96 out of 5 average rating, 116 reviews

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the historic triangle, or just take it easy around the house and enjoy the outdoor area, the choice is yours.

Home in Williamsburg

4.98 out of 5 average rating, 202 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

Home in Olde Towne

4.98 out of 5 average rating, 123 reviews

Gorgeous Olde Towne historic home - modern updates

Full of historic charm, modern in all the right places! This 1880s home is located in the heart of Olde Towne Portsmouth, just one block from the Elizabeth River harbor. Walk 3 minutes to the ferry stop and ride across the river to Norfolk's downtown and waterfront restaurants, or walk 5 minutes to Portsmouth's High Street to enjoy Olde Towne's charming coffee shops, restaurants, museums, and theaters. This location is unbeatable!

Home in Hampton

4.83 out of 5 average rating, 108 reviews

Hampton River Retreat Deluxe

The Hampton River Retreat Deluxe is a newly renovated 3 Bedroom/2 bath home on the Hampton River - conveniently located by land or water to all major points in the Hampton Roads area. The quiet neighborhood is close to many features including Downtown Hampton, Langley AFB, Fort Monroe, Buckroe Beach, and a short drive across the HRBT to Norfolk. No parties or events, or gatherings of any kind are allowed in the home.

Home in Virginia Beach

4.91 out of 5 average rating, 238 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.

Home in East Ocean View

4.92 out of 5 average rating, 122 reviews

Cozy beach cottage! One block to the beach!

Beach cottage! Dogs sleep for free! One block to the beach. 3 bedroom. 1 bath. 1 king, 1 queen and 2 twin beds. Large deck with outdoor seating and grill! One block from Karla’s Beach House (brunch and lunch). One block from Jessy’s Taqueria. About a mile from Cova Brewing Co. (Brewery and Coffee) and East Beach Farmer’s Market (Saturdays from 9-12). EV Charger on premises. Up to 2 dogs allowed.

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Popular amenities for Portsmouth house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Portsmouth

4.94 out of 5 average rating, 85 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Home in Virginia Beach

4.82 out of 5 average rating, 112 reviews

THE OLD BEACON 1 | Beach Living

Home in Virginia Beach

4.94 out of 5 average rating, 106 reviews

Country Comfort Close to the Beaches

Home in Phoebus

4.85 out of 5 average rating, 181 reviews

Waterfront home with heated pool available!

Home in East Ocean View

4.98 out of 5 average rating, 49 reviews

The Seaglass Cottage

Home in Portsmouth

4.83 out of 5 average rating, 23 reviews

Elegance Escape on Saunders Dr

Home in Sandbridge

4.85 out of 5 average rating, 119 reviews

Stunning Views of Back Bay & Seconds to the Beach

Home in Suffolk

4.83 out of 5 average rating, 78 reviews

Perfect Getaway!

Weekly house rentals

Home in Portsmouth

4.95 out of 5 average rating, 41 reviews

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Home in Portsmouth

5 out of 5 average rating, 35 reviews

Waterfront/Arcade/Fishing Fun

Home in Portsmouth

4.9 out of 5 average rating, 59 reviews

Quiet Churchland Gem

Home in Portsmouth

4.9 out of 5 average rating, 10 reviews

Broadway by the Water

Home in Portsmouth

4.92 out of 5 average rating, 13 reviews

Perfectly cozy MCM design 3 bedroom home fast WiFi

Home in Portsmouth

5 out of 5 average rating, 27 reviews

Riverfront Home w/ Vintage Vibes

Home in Portsmouth

4.95 out of 5 average rating, 19 reviews

YES Queen! The Bridgerton House

Home in East Ocean View

4.94 out of 5 average rating, 86 reviews

The OV Beach Shack : cozy, fun beach house!

Private house rentals

Home in Olde Towne

4.94 out of 5 average rating, 18 reviews

Tudor Treasure in Olde Towne

Home in Buckroe Beach

4.93 out of 5 average rating, 54 reviews

Tiny Home In Buckroe Beach

Home in Norfolk

4.92 out of 5 average rating, 72 reviews

Tiny House Near Beach & Naval Base - Privacy Fence

Home in Chesapeake

4.96 out of 5 average rating, 75 reviews

Cook's Country Escape - House nestled in woods

Home in Buckroe Beach

4.87 out of 5 average rating, 38 reviews

Tiny Blue Beach House

Home in Olde Towne

4.8 out of 5 average rating, 30 reviews

Historic Old Towne Garden of Lotus

Home in Portsmouth

4.84 out of 5 average rating, 19 reviews

3 Bedroom near Rivers Casino!

Home in Portsmouth

4.98 out of 5 average rating, 58 reviews

Waters Edge Retreat!

Quick stats about house rentals in Portsmouth

Total rentals
300 properties
Total number of reviews
8.6K reviews
Family-friendly rentals
170 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
170 properties have a dedicated workspace

Destinations to explore