House vacation rentals in Chesapeake

A spacious living area is presented, featuring a large flat-screen television mounted on a wooden console. A comfortable seated area includes plush armchairs and a sofa, while natural light enters through a window, complementing the neutral carpet and walls.

4.88 out of 5 average rating, 112 reviews

3 bedroom home, King's Forest Va. Beach, Virginia

Quiet neighborhood in the heart of Va. Beach w/ private driveway, 100 yds from a huge park w/ tennis courts, playground, long paved walking trail, grills & fishing pond. Blocks to the interstate, 6 miles to the Ocean Front and 2 miles to Town Center! I live in my own space behind the main house. The home is 100% private, soundproof and completely in your hands. My guests are thrilled to have a private home and an easily reached fix everything guy when needed! IMPORTANT! NO SMOKING INSIDE HOUSE.

4.86 out of 5 average rating, 124 reviews

The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.

Home in West Park View

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

4.94 out of 5 average rating, 140 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

4.96 out of 5 average rating, 111 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

5 out of 5 average rating, 132 reviews

A modern kitchen features white cabinetry and a granite countertop, equipped with stainless steel appliances including a stove and a refrigerator. Under-cabinet lighting enhances the space, and ample storage is provided by multiple upper and lower cabinets. A sink is positioned near a window, allowing natural light.

Home in East Ocean View

Quiet East Beach Bungalow, 1 block to beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! A quick walk to the beach or Bay Oaks Park, this bungalow is perfect for relaxing getaways. Fireplace, patio, grill, spacious front porch, new appliances, washer/dryer, private off-street parking. A quick trip to the Naval Bases! Guests are provided with linens, towels, toiletries, and high speed internet(SmartTV). Additional rooms available case by case basis. Please ask.

A cozy living room is featured, showcasing a light-colored sofa paired with two yellow accent chairs. A wooden coffee table sits at the center, and two windows are dressed with sheer curtains, allowing gentle light to brighten the space. A ceiling fan is present above.

4.96 out of 5 average rating, 121 reviews

The Cozy Cottage Two Bedroom, King bed House

This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

4.84 out of 5 average rating, 133 reviews

A coffee table is adorned with a lit candle, a notebook, and two books. Comfortable blue chairs are positioned in the background, while a patterned rug adds warmth to the space. Soft natural light illuminates the room, enhancing the decor.

Home in Willoughby

Bungalow at the Bay

This wonderfully decorated home is the perfect spot for a beach getaway with the whole family. Inside you will find a spacious living room, kitchen, bathroom, and two guest rooms with one queen, and a full. Outside there is a backyard porch, perfect for socializing, and a sizable backyard protected by a fence that stretches the property! Free parking is available inside and outside the property. Beach access and free parking is located on 11th view street about a two-minute walk away!

A cozy living area features two armchairs and a leather sofa, arranged around a circular coffee table on a patterned rug. A fireplace is situated against the wall, complemented by a television mounted above. Natural light is allowed in through the window with white blinds.

4.85 out of 5 average rating, 142 reviews

Beach Hideaway 2 bdr/2bth- Pet friendly!

Great home for days at the beach and a fire pit at night! Beach access 1 1/2 blocks from the home. Heat/AC, dishwasher, w/d, and deck. Linens, bath towels, beach chairs, and beach towels are provided. Quiet family beach, bay water is calm- perfect for children. Large back yard for kids to run around, deck, and enclosed front porch. Close to Virginia Beach, Norfolk military bases and ODU, EVMS, NSU, Virginia Wesleyan, Hampton Univ. Approx 25 min from downtown Virginia Beach and W-burg.

4.94 out of 5 average rating, 130 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

Home in Knotts Island

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

4.85 out of 5 average rating, 106 reviews

A two-story house featuring a welcoming porch with white railings and steps leading to the front door. The exterior is clad in light siding, complemented by well-kept landscaping and a driveway leading to a garage on the right. Trees provide a natural backdrop.

Home in Suffolk

Perfect Getaway!

Home away from home!! Beautiful 2 story house with 3 bedrooms, 3 bathrooms, and a huge playroom over the garage. The master suite has a beautiful bathroom with a jacuzzi tub, and huge walk in shower. The fenced in backyard has plenty of space to run around, and has an awesome saltwater inground pool for fun! In addition, there is a 2 level, new deck, and patio furniture to sit and relax on. There is something for everyone to do here.. I’m positive you will love it!

4.98 out of 5 average rating, 172 reviews

The living room features comfortable navy sofas with decorative cushions and an ottoman in a warm tone. A lamp stands beside a built-in bookshelf adorned with books and decor. Light streams through the windows, and a decorative fireplace adds to the room's character.

Home in Olde Towne

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!

A charming, two-story home with a light blue exterior is surrounded by tall trees and a well-maintained lawn. The roof features dark shingles, while steps lead to a welcoming front door, framed by greenery. Sunlight filters through leaves, creating a serene atmosphere.

4.8 out of 5 average rating, 256 reviews

Waterfront Maryview/Naval Hosp Casino close to all

This lovely, quaint home has been completely updated for your comfort. The great room is bright and open. The home is located on the Elizabeth River in an upscale neighborhood with a large yard. This is perfect for a family vacation, or a long weekend. There is an attached mother-in-law suite in the rear of the house. This is rented out separately. It has a private entrance at the rear of the house.

Popular amenities for Chesapeake house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A charming coastal cottage exterior is depicted, featuring a white clapboard façade and a shingled roof. The blue front door is framed by decorative shutters, with a welcoming wreath displayed. An American flag hangs proudly, completing the inviting entrance.

4.83 out of 5 average rating, 144 reviews

THE OLD BEACON 1 | Beach Living

4.99 out of 5 average rating, 203 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

A private pool area features comfortable lounge chairs with floral cushions, surrounded by a clean concrete patio. A screened-in porch is visible in the background, with two inviting chairs for relaxing. The fenced yard offers additional privacy and space for outdoor enjoyment.

4.96 out of 5 average rating, 90 reviews

Paint The Beach Pink! Full House | Private Pool

A spacious brick home is surrounded by well-maintained landscaping featuring lush green grass and mature trees. The front porch, adorned with potted plants, provides a welcoming entrance. Natural light filters through the windows, enhancing the overall charm of the property.

4.95 out of 5 average rating, 121 reviews

Country Comfort Close to the Beaches

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

4.92 out of 5 average rating, 118 reviews

Gorgeous Vacation House

4.82 out of 5 average rating, 136 reviews

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

4.97 out of 5 average rating, 222 reviews

Salida del Sol, North End Beach

An inviting entrance features a black bench topped with a decorative pillow and a soft throw. A round mirror complements the space, while natural light floods the area through large windows, revealing a cozy living room area with a stone fireplace and wooden beams overhead.

5 out of 5 average rating, 9 reviews

Farmhouse Retreat-POOL, Sauna, 10 min to BEACH

Weekly house rentals

4.98 out of 5 average rating, 44 reviews

A bright living space features large windows offering panoramic views of Chesapeake Bay. A comfortable leather sofa and colorful area rug are positioned around a wooden coffee table. A decorative mirror and fireplace add interest to the room, while a stylish desk is situated nearby.

Home in East Ocean View

Private Beachfront Modern Villa: Outdoor Shower!

A light-filled living area features a comfortable sectional sofa and a coffee table centered on a textured rug. Adjacent, a dining table accommodates several chairs, while a wall-mounted television is positioned above a decorative fireplace. Windows provide views of the outdoor space.

4.92 out of 5 average rating, 48 reviews

3 bd home, close to shopping and dining!

A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.

4.95 out of 5 average rating, 80 reviews

R & R River House

5 out of 5 average rating, 20 reviews

Relaxing 3BR River Stay • 8 Mins to Casino!

5 out of 5 average rating, 11 reviews

The Main House

A modern living room is showcased with light hardwood flooring and elegant furnishings. A large flat-screen TV is mounted on a marble feature wall, while a plush sofa is positioned nearby. Natural light flows in through large windows adorned with sheer curtains.

5 out of 5 average rating, 95 reviews

Beach Stay

A modern kitchen features light cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are visible. Soft lighting highlights the spacious layout, which is complemented by tiled flooring and a seamless flow into the adjacent dining area.

5 out of 5 average rating, 81 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

A modern living area features a comfortable gray sectional sofa complemented by a patterned area rug. Wooden coffee tables with decorative plants are positioned in front of the seating. A well-lit dining space is visible in the background, along with sleek appliances in the adjoining kitchen.

4.86 out of 5 average rating, 42 reviews

Historic Haven

Private house rentals

4.66 out of 5 average rating, 71 reviews

Chesapeake. Comfy & Cozy. 4 Beds 2 Bath

The exterior of a single-story home features a brick facade complemented by white paneling. A covered entryway protects the front door, and well-maintained landscaping with small plants and a pathway leads up to the entrance. Windows allow natural light to enter the interior.

4.77 out of 5 average rating, 74 reviews

Southern Charm Warm and Welcome

A modern gray sectional couch is positioned against a light gray wall. It features several decorative pillows in varying shades. Two table lamps with simple shades stand on either side on dark side tables, and a patterned area rug covers the hardwood floor.

5 out of 5 average rating, 13 reviews

The Mayfield

4.71 out of 5 average rating, 7 reviews

Cozy 3Bed/3Bath Home near Portsmouth Naval-Casino

A classic Cape Cod home is surrounded by well-maintained greenery. The brick exterior is complemented by a gravel pathway leading to the front steps. A concrete driveway provides access to an attached garage, while flags are displayed on the front porch, enhancing the home's welcoming appearance.

4.97 out of 5 average rating, 35 reviews

The Bartlett Inn

A modern dining area features a round table with a sleek black surface, surrounded by stylish chairs. A small potted plant sits at the center. The open-concept kitchen is visible in the background, showcasing light cabinetry and stainless steel appliances.

4.93 out of 5 average rating, 15 reviews

Portsmouth's Finest

A modern living room is presented, featuring a spacious sectional sofa with light fabric. A wall-mounted smart TV dominates the area, and a glass coffee table is placed in front. Two black bar stools are positioned near a kitchen counter in the background, enhancing the open layout.

4.93 out of 5 average rating, 15 reviews

Home Away From Home