Portsmouth vacation rentals

A spacious bedroom features a large bed with fresh linens, complemented by a wooden bench at the foot. Light-colored walls and hardwood floors enhance the airy feel. Natural light floods in through shuttered windows, and bedside lamps provide soft illumination.

4.93 out of 5 average rating, 15 reviews

Incredible Location! Amazing Comfort!

Location, Location, Location!! Approximately 200 yards from your toes in the sand and the incredible blue Atlantic. A home away from home with all the amenities you could possibly need to make your stay, or extended stay a comfortable and memorable experience. The bunk room is ideal for an extended family or a comfortable room only for the little people. Virginia Beach has everything you need whether you're coming for vacation, relaxation, activity, or work. Experience Virginia Beach while stayi

Guesthouse in Gloucester County

4.98 out of 5 average rating, 153 reviews

Modern Moody Cabin w/ Hot Tub Creek View Fire Pit

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

4.94 out of 5 average rating, 116 reviews

A charming café building features a pale yellow exterior with blue accents. Outdoor seating is arranged with black metal chairs and tables under bright blue umbrellas. Potted plants border the entrance, enhancing the inviting atmosphere of the Coastal Baking Company.

Home in Cape Charles

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

4.96 out of 5 average rating, 103 reviews

Home in Cape Charles

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

Guest suite in Virginia Beach

Soft illumination from ground-level lights highlights the lush landscaping surrounding the property. Various plants and flowers are visible, and a calm ambiance is created by the gentle glow. In the background, trees silhouette against the evening sky, enhancing the serene setting.

4.98 out of 5 average rating, 147 reviews

Quiet Suite with Private Entrance

Looking for a place to relax away from the chaos of the oceanfront? Quiet, private and secluded but conveniently located. Less than a 10 minute drive to the beach. Walking distance to breweries, local restaurants, grocery stores and other amenities Beautiful 2 acre property with plenty of outdoor space to find a place to relax, play games or take a nap Leesa king size mattress Luxurious bathroom with soaker tub Microwave and fridge, Kurig, k-cups snacks and popcorn Smart TV, WiFi

Townhouse in Virginia Beach

A spacious bedroom features a large, comfortable bed with a textured white coverlet and decorative pillows. A modern television is mounted on the wall opposite. Natural light filters through sheer curtains, highlighting a private balcony with a small table and chairs.

5 out of 5 average rating, 46 reviews

Wave Break Hideaway

Welcome to your perfect beach getaway in Virginia Beach's vibrant Vibe district! Enjoy this centrally located, stylish townhome, located one block from the future Atlantic Park. You're near eclectic restaurants, breweries, and entertainment! Now under new ownership, we're committed to the same attention to detail that made this a top rental in the past. Enjoy sunsets on your private balcony. Ideal for romantic getaways or family vacations. Book now for an unforgettable experience!

4.94 out of 5 average rating, 63 reviews

A sparkling swimming pool is framed by lounge chairs with a clear view of the ocean in the background. The pool features a vibrant lane marker along its length, and the bright blue sky reflects onto the water's surface.

Condo in Sandbridge

Cher's Place @ The Beach

Relax with the whole family at this peaceful place to stay in Sandbridge! This property is ON the beach (unit itself is not facing the ocean) with access to 3 pools, a gym, local restaurants and much more! As you can see, guests LOVE my place! I frequently travel for work, spending a lot of time in hotel rooms. I know the NECESSITIES! ** I am currently replacing furniture and bedding so pics may not match perfectly. Need more room?? See my other property!

A serene sunset is captured over calm ocean waters, where hues of orange and pink blend softly into the sky. The horizon is defined by the setting sun, reflecting light across the water's surface, creating a peaceful atmosphere.

4.96 out of 5 average rating, 194 reviews

Sunrise, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!

Tiny home in Cape Charles

A welcoming porch features a vibrant coral door framed by two windows. Light-colored outdoor chairs are arranged around a small table, complemented by a decorative mat and nautical-inspired decor. The covered area provides a cozy spot to relax outside.

4.88 out of 5 average rating, 121 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

4.98 out of 5 average rating, 57 reviews

Two white Adirondack chairs are positioned beside a small table on a wooden deck overlooking the water. The tranquil Chesapeake Bay is visible, with green trees lining the shore and a clear blue sky above, providing an inviting space for relaxation.

Guesthouse in Hampton

Fantastic Getaway

You need to see this fully furnished, stunning guest house located along the historic section of Chesapeake Ave. Wake-up to breathtaking views of the Chesapeake Bay. Great fishing, crabbing, sailing, bike trails, kayaking and more. Enjoy herons, osprey, dolphins and other wildlife. Centrally located to shopping, casinos, restaurants and public beaches!

5 out of 5 average rating, 48 reviews

Home in Cape Charles

Captain's Cottage

The Captain's Cottage was originally built in 1886 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Cape Charles's Central Park, four blocks from the beach, and two blocks from Mason Avenue, the Captain's Cottage is in a prime location in Cape Charles.

4.89 out of 5 average rating, 132 reviews

Beach Home, Upscale Croatan Resort + Private Pool

This spacious Atlantic Ocean view beach home is breathtaking. Only a two minute walk to the private beach area in the Upscale Croatan neighborhood. Beautiful Atlantic ocean, boardwalk views, and the inlet from decks. Pool and grill in backyard and a grill off third floor kitchen deck entrance.

Vacation rentals for every style

Get the amount of space that is right for you

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A space thats all yours, with room for everyone

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Popular amenities for Portsmouth vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Portsmouth's top sights

Waterside20 locals recommend

Chrysler Museum of Art184 locals recommend

Nauticus162 locals recommend

MacArthur Center153 locals recommend

Waterside District143 locals recommend

USS Wisconsin BB-6486 locals recommend

Other great vacation rentals in Portsmouth

4.98 out of 5 average rating, 61 reviews

The kitchen features modern appliances, including a stainless-steel stove, microwave, and refrigerator. Light-colored cabinets contrast with the granite countertops. A window offers natural light, while a clock and decor elements add functional touches to the space.

Home in Chesapeake

Sleeps 6-8, King bed, 2.5 baths

5 out of 5 average rating, 7 reviews

Home in Newport News

Spacious Family Getaway | 7BR | 3 masters | 5 Bath

4.95 out of 5 average rating, 37 reviews

Home in Norfolk

Family Getaway | 1 Block from Beach | Game Room

Guest suite in Chesapeake

An outdoor space features a shaded patio area with a grill, comfortable red seating, and a dining set. Decorative lights create a festive atmosphere, while an American flag hangs proudly. A lush green lawn and wooden fence frame the scene, enhancing the backyard's privacy.

4.93 out of 5 average rating, 280 reviews

King Guest Suite - A Family Vacation Rental

5 out of 5 average rating, 69 reviews

Home in Surry

Waterfront on the James 4,100 SF near Williamsburg

5 out of 5 average rating, 24 reviews

Home in Sandbridge

Pool, hot tub, walk to beach, family friendly home

4.6 out of 5 average rating, 210 reviews

A charming two-story house is depicted with a white exterior and dark green shutters. Red window frames accentuate the front windows, while two circular wall decorations add character. A shaded walkway leads to the entry, surrounded by neatly maintained shrubs and lawn.

Home in Williamsburg

GR8 Family Vacation Rental