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Vacation rentals in Chesapeake

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Quick stats about vacation rentals in Chesapeake

  • Total vacation rentals

    Explore 950 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at R 159 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 37,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    450 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 280 rentals that welcome pets

  • Vacation rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    480 properties have a dedicated workspace

  • Wi-Fi availability

    890 of Chesapeake vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Gym, and BBQ grill across Chesapeake rentals

  • 4.8 Average rating

    Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Aerotheater

Top-rated vacation rentals in Chesapeake

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

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Top guest favorite
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.
Home in Portsmouth
5.0 out of 5 average rating, 111 reviews

Hidden Gem.4/bedroom cozy home fenced in yard

Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

Guest favorite
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.
Home in Portsmouth
4.92 out of 5 average rating, 173 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guests, 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!

Guest favorite
A spacious living area features a soft sectional sofa adorned with decorative pillows. A glass-top coffee table is centered on a patterned rug, flanked by side tables with lamps. Natural light streams through two large windows, complemented by light curtains.
Home in Chesapeake
4.96 out of 5 average rating, 104 reviews

2 Master Suites, Sleeps 6-8, King bed, 2.5 baths

Bring the whole family to this spacious home with plenty of room to relax. This is one side of a duplex featuring two master suites, each with its own en-suite bathroom, plus a convenient half bath downstairs. The home includes a king bed in one suite and two queen beds in the second, along with walk-in closets, washer and dryer, central heat and air, and a wonderful deck. Centrally located. Traveling with a larger group? Both sides of the duplex can be booked to accommodate up to 16 guests.

Top guest favorite
A modern kitchen features light cabinetry and granite countertops, complemented by stainless steel appliances. An island with two stools offers additional seating, and a window allows natural light to brighten the space. Essential kitchen items are neatly arranged on the countertop.
Apartment in Chesapeake
4.98 out of 5 average rating, 123 reviews

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor (stair access) above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

Top guest favorite
A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.
Home in Virginia Beach
4.99 out of 5 average rating, 235 reviews

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

Guest favorite
A spacious living room features a neutral color palette, highlighted by a cozy couch and two armchairs. A wooden coffee table is centered in front of a decorative fireplace adorned with greenery and accessories. Natural light enters through large windows, enhancing the inviting setting.
Townhouse in Chesapeake
4.9 out of 5 average rating, 193 reviews

Family friendly townhouse

A perfect place to stay when you can't be at home!Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large primary bedroom with private bathroom and shower. Washer and dryer in t

Superhost
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.
Home in Norfolk
4.94 out of 5 average rating, 139 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 space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Bring your fishing poles!

Top guest favorite
A cozy bedroom features a four-poster bed adorned with soft linens and decorative pillows. A vintage armchair is positioned nearby, while a window dressed with light blue curtains allows natural light to brighten the space. Subtle wall stripes in calming colors add character.
Home in Chesapeake
4.96 out of 5 average rating, 143 reviews

Cook's Country Escape - Cozy Retreat

Escape the everyday and enjoy this cozy countryside retreat! Nestled halfway between Virginia Beach and the Outer Banks, this home offers the charm of a cabin with the comforts of a full house. Perfect for families or friends, it’s a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, you’ll feel the warmth and relaxation of a true country home. It’s been a great rental with great ratings.

Superhost
The living room features a welcoming layout with plush blue couches and two light-colored round ottomans. A ceiling fan hangs above, and natural light streams in through multiple windows. The front door is painted in a vibrant teal, adding a cheerful touch.
Home in Norfolk
4.91 out of 5 average rating, 110 reviews

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ

Escape to our charming Airbnb, just steps from the beach! Perfect for groups up to 8, our home offers ultra-fast 1Gbps fiber internet, a dedicated workspace, and delightful amenities including a SCA-approved coffee maker, a grinder, and fun games like a giant Connect 4 and Foosball. Enjoy the outdoors with our two patios and a BBQ grill. With numerous local restaurants nearby, it’s the ideal getaway for both relaxation and adventure.

Superhost
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 Portsmouth
4.99 out of 5 average rating, 215 reviews

Historic Gem - Walk to Dining, Ferry & Waterfront

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!

Top guest favorite
The Purple Room features a spacious bed with white linens and purple accents. A cozy seating area is visible beside large windows with light filtering through sheer curtains. Decorative elements, including wall art and a soft purple rug, enhance the vibrant atmosphere.
Guest suite in Chesapeake
4.97 out of 5 average rating, 394 reviews

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, where every guest is made to feel like royalty. More than an Airbnb, it’s a one-of-a-kind boutique retreat intentionally designed to create unforgettable memories. From the peaceful atmosphere and thoughtful touches to your private entrance and relaxing escape, every detail has been curated to help you unwind, recharge, and experience something truly special. Come discover The Purple Room experience. 💜

Guest favorite
The exterior of a private attached suite is shown, featuring a welcoming entrance with white steps and a small porch. Lush greenery and colorful flowers frame the walkway, leading to a paved driveway. A wooden fence provides privacy, while a well-maintained lawn enhances the setting.
Guest suite in Chesapeake
4.94 out of 5 average rating, 679 reviews

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. NOTE: Pool is open from Memorial Day to Labor Day. 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.

Popular amenities for Chesapeake vacation rentals

Self check-inGymBBQ grillLaptop-friendly workspaceWifi

Stay near Chesapeake's top sights

Nauticus

254 locals recommend

Chrysler Museum of Art

250 locals recommend

MacArthur Center

175 locals recommend

Topgolf

157 locals recommend

Lynnhaven Mall

141 locals recommend

Virginia Museum of Contemporary Arts

138 locals recommend

Other great vacation rentals in Chesapeake

Top guest favorite
A brick house is presented, featuring a traditional single-story design. A large front lawn is visible, complemented by trees in the background. The home is accented by a welcoming front door and large windows, with a driveway leading to an attached garage.
Home in Chesapeake
4.94 out of 5 average rating, 65 reviews

Quiet 3/2 beautiful Chesapeake

Guest favorite
Home in Chesapeake
4.91 out of 5 average rating, 90 reviews

Comfy House! The Perfect Getaway

Guest favorite
A dining area features a sleek wooden table surrounded by six chairs. Above, a chandelier provides soft lighting. The space connects to a well-lit living area visible in the background, with a modern recliner and additional furnishings enhancing the room's functionality.
Home in Chesapeake
4.98 out of 5 average rating, 40 reviews

Simply Amazing in Chesapeake

Guest favorite
A bright living area features a light-colored sofa adorned with patterned cushions. A round wooden coffee table sits on a colorful area rug, and a wall-mounted television displays a scenic landscape. Sunlight enters through partially open window treatments, complementing the room's neutral tones.
Home in Chesapeake
4.85 out of 5 average rating, 39 reviews

Cowbell Cottage

Guest favorite
Townhouse in Chesapeake
5.0 out of 5 average rating, 11 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

Top guest favorite
A cozy bedroom is showcased, featuring a spacious bed with decorative bedding and pillows. A small white chair is placed at the foot of the bed. Wall-mounted shelves display various items, while a lamp provides soft lighting next to the bed. The grey walls create a calming backdrop.
Home in Chesapeake
4.91 out of 5 average rating, 65 reviews

The Bird’s Nest

Top guest favorite
Home in Norfolk
4.95 out of 5 average rating, 39 reviews

Blessed and peaceful home

Top guest favorite
Home in Chesapeake
4.93 out of 5 average rating, 70 reviews

Spacious 3 Bedroom Home | Near many Shops & Dining

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 1,659 ZARR 1,627 ZARR 1,659 ZARR 1,802 ZARR 1,914 ZARR 2,057 ZARR 1,946 ZARR 1,914 ZARR 1,706 ZARR 1,738 ZARR 1,754 ZARR 1,770 ZAR
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

Frequently Asked Questions

  • What are the best places to stay in Chesapeake?

    Greenbrier, Great Bridge, and South Norfolk neighborhoods are frequently suggested for their proximity to parks, shops, and dining. Staying near outdoor spaces such as Chesapeake City Park provides easy access to family activities.

  • What are the best things to do in Chesapeake with kids?

    Children often enjoy playgrounds and family-friendly events at Chesapeake City Park, hands-on activities at the local children’s museum, and hiking in Northwest River Park. Seasonal festivals add extra entertainment during spring and summer.

  • What are some of the best things to do in Chesapeake?

    Explore the trails at the Great Dismal Swamp National Wildlife Refuge, visit Chesapeake Arboretum’s wooded gardens, and bring a picnic to Chesapeake City Park. You can also discover local shops and waterfront areas around South Norfolk.

  • How is the weather in Chesapeake?

    Chesapeake has winters around 34–51°F (1–10°C) with regular rainfall, and summers near 73–89°F (23–32°C), marked by warm afternoons and higher humidity. Spring and autumn are usually mild with comfortable temperatures and blooming landscapes.

  • When is the best time to visit Chesapeake?

    Late spring and early autumn are often recommended for mild weather and outdoor festivals. During these seasons, temperatures range from about 55–77°F (13–25°C), and the city’s parks and nature reserves are popular for hiking and family outings.

  • What are the best places to visit in Chesapeake?

    Popular places to visit in Chesapeake include the Great Dismal Swamp National Wildlife Refuge, Chesapeake Arboretum, and Northwest River Park. These spots have trails, gardens, and opportunities for wildlife viewing and outdoor recreation.

  • What are some hiking trails in Chesapeake?

    Hiking trails in Chesapeake can be found at the Great Dismal Swamp National Wildlife Refuge, Northwest River Park, and Chesapeake Arboretum. Trails wind through woodlands, wetlands, and natural habitats for varied outdoor experiences.

  • What are some family activities we can do in Chesapeake?

    Families often explore Chesapeake City Park for playgrounds and picnics, hike trails in the Great Dismal Swamp National Wildlife Refuge, or enjoy interactive exhibits at the local children’s museum. Outdoor adventure and hands-on fun are popular for all ages.

  • What are some of the best day trip ideas from Chesapeake?

    Day trip ideas include exploring the Great Dismal Swamp National Wildlife Refuge, visiting beaches near Virginia Beach, or checking out historic sites and museums in Norfolk. The area has nature, cultural attractions, and local markets worth discovering.

  • Are there any pet friendly accommodations available in Chesapeake?

    Many vacation rentals in Chesapeake welcome pets, especially in areas like Greenbrier, Great Bridge, and near the city’s parklands. Parks such as Chesapeake City Park have designated areas for dogs to enjoy.

  • What are some local tips for visiting Chesapeake?

    Locals suggest exploring nature reserves in the morning for calmer trails, and bringing binoculars to enjoy birdwatching. Neighborhoods such as South Norfolk have locally rooted shops and cafes, and many parks are pet friendly.

  • What is Chesapeake known for?

    Chesapeake is known for its extensive wetlands, the Great Dismal Swamp, and vibrant community festivals. The city also has a mix of outdoor spaces, waterways, and a history rooted in agriculture and trade.

  • What are the best hidden gems to explore in Chesapeake?

    The Chesapeake Arboretum, featuring woodland trails and gardens, and the Great Dismal Swamp National Wildlife Refuge are often suggested for those seeking serene outdoor spaces. You might also discover local art studios and historic sites around South Norfolk.

  • What are the best foods to try in Chesapeake?

    Chesapeake is known for coastal and Southern flavors, with crab dishes, oysters, barbecue, and cornbread frequently suggested. Local produce and seasonal seafood can be found at markets and family-owned restaurants around the city.

  • What should I bring for a trip to Chesapeake?

    For a trip to Chesapeake, pack comfortable shoes and waterproof layers, especially in the wetter summer months. Sunscreen and insect repellent are helpful for outdoor activities, and a reusable water bottle is useful for exploring parks and trails.

  • What is the nightlife in Chesapeake like?

    Nightlife in Chesapeake is often centered around casual dining, sports bars, and live music venues, especially in neighborhoods such as Greenbrier and Great Bridge. Atmospheres are relaxed, with occasional local performances and spots for late-night bites.

  • What are the most popular events or festivals in Chesapeake?

    Chesapeake has seasonal events, including fairs and outdoor festivals, that often take place in late spring and autumn. The Chesapeake Wine Festival and the Chesapeake Jubilee are among the most popular recurring community gatherings.

  • Are there family friendly vacation rentals in Chesapeake?

    Chesapeake has many family friendly vacation rentals, with neighborhoods near nature reserves and parks often suggested for travelers with children. Look for homes in areas surrounding Greenbrier, Great Bridge, or near parkland for easy access to outdoor spaces.

Destinations to explore