Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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Top guest favorite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 707 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

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 Western Branch
4.96 out of 5 average rating, 362 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!

Top guest favorite
A serene sunset view is captured over the Elizabeth River, with vibrant hues of orange and pink filling the sky. Silhouetted trees frame the scene, while a peaceful dock extends into the water, inviting moments of reflection and tranquility.
Cottage in Norfolk
5 out of 5 average rating, 290 reviews

Beautiful Cottage Waterfront Near Downtown Norfolk

A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

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
4.94 out of 5 average rating, 154 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!

Top guest favorite
A dining area features a wooden table set for six, accompanied by cross-back chairs. A standing lamp casts soft light. Large windows above allow natural light to illuminate the space, while a few pieces of artwork add a splash of color to the walls.
Apartment in Chesapeake
4.99 out of 5 average rating, 179 reviews

Modern Luxury Peace & Quiet.

Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Top 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 Greenbrier
4.95 out of 5 average rating, 628 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.

Guest favorite
A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.
Cabin in Cape Charles
4.95 out of 5 average rating, 216 reviews

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

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 Great Bridge
4.89 out of 5 average rating, 168 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

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 Great Bridge
4.97 out of 5 average rating, 107 reviews

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor 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.

Guest favorite
A two-story garage features a sloped roof and a set of double windows on the upper level. A concrete driveway extends beside it, flanked by greenery and a seating area. Sunlight illuminates the space, enhancing its inviting appearance.
Guesthouse in Western Branch
4.91 out of 5 average rating, 109 reviews

Western Branch Loft Suite

Enjoy your own space in this quiet studio located near Navy bases, hospitals, and the beach. It’s perfect for those looking for a little bit of peace while they are in the area for work, house hunting, visiting family or friends. This comfy guesthouse is in a safe neighborhood 5 minutes from grocery stores, restaurants, gyms, and highways to get around. Avoid the busiest traffic areas here while still being able to enjoy a day trip to the beach!

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
4.97 out of 5 average rating, 127 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.

Guest favorite
A spacious room features a king-size bed with a soft white bedspread and dark accent pillows. A seating area with a leather futon and dining table for four is present. Natural light enters through a large window, complemented by dark curtains. A small fridge is positioned nearby.
Guest suite in Chesapeake
4.92 out of 5 average rating, 298 reviews

King Guest Suite - A Family Vacation Rental

Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

Popular amenities for Chesapeake vacation rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,700 ZARR1,700 ZARR1,785 ZARR1,870 ZARR1,955 ZARR1,989 ZARR2,074 ZARR2,040 ZARR1,819 ZARR1,853 ZARR1,870 ZARR1,887 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.

Quick stats about vacation rentals in Chesapeake

  • Total vacation rentals

    Explore 980 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at R170 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 36,930 verified reviews to help you choose

  • Family-friendly vacation rentals

    450 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 300 rentals that welcome pets

  • Vacation rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    520 properties have a dedicated workspace

  • Wi-Fi availability

    940 of Chesapeake vacation rentals include wi-fi access

  • Popular amenities for guests

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

  • 4.7 Average rating

    Chesapeake stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

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

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