Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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Top guest favourite
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, 359 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 favourite
A cheerful cottage is framed by tall trees and surrounded by a spacious lawn. The front porch features white railings and a welcoming green door. A mailbox stands at the edge of a quiet road, highlighting the tranquil neighborhood setting.
Cottage in Sunbury
4.97 out of 5 average rating, 130 reviews

The Little House on Park Avenue

Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Guest favourite
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
4.97 out of 5 average rating, 120 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. Oh & bring your fishing poles, river is fully stocked!

Top guest favourite
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.
Flat in Chesapeake
4.99 out of 5 average rating, 176 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.

Guest favourite
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, 624 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 favourite
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, 214 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.

Top guest favourite
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
4.85 out of 5 average rating, 107 reviews

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!

Top guest favourite
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.
Flat in Great Bridge
4.97 out of 5 average rating, 105 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.

Top guest favourite
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, 125 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 favourite
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!

Superhost
A comfortable living area is furnished with a plush sofa and an accent chair. A large television is mounted on the wall, and a decorative sign above adds a touch of character. Light wood cabinets are visible in the background, enhancing a spacious feel.
Flat in Chesapeake
4.89 out of 5 average rating, 148 reviews

2 BR With King. āš”ļøFast Wifi. šŸ” Easy Self Check-In.

Welcome to Casa de Curtin This apartment features a full kitchen w/ dbl sink, refrigerator, washer, dryer, range, microwave, Keurig, table & chairs. The living room has a plush, oversized sofa & chair set & two 4K smart tvs & fast WiFi. Br’s have a King & Queen comfortable beds and ceiling fans and there is a large full bth w/ walk-in shower and vent fan. Smart locks make self check-in a breeze! Located close to VA Beach.

Top guest favourite
The exterior of a two-story brick apartment building is shown, featuring a staircase leading to the entrance. Lush green shrubs and trees frame the entrance, while a driveway accommodates two blue recycling bins. A neighboring structure is visible to the left.
Guest house in Chesapeake
4.98 out of 5 average rating, 253 reviews

Beautiful and Chic Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

Popular amenities for Chesapeake holiday rentals

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹9,237₹9,237₹9,698₹10,160₹10,622₹10,807₹11,269₹11,084₹9,883₹10,068₹10,160₹10,253
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 holiday rentals in Chesapeake

  • Total holiday rentals

    Explore 980 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at ₹924 per night before taxes and fees

  • Verified guest reviews

    Over 36,930 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 300 rentals that welcome pets

  • Holiday rentals with a pool

    130 properties feature pools

  • Rentals with dedicated workspaces

    520 properties have a dedicated workspace

  • Wifi availability

    940 of Chesapeake holiday rentals include wifi 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 Cinema Cafe-Greenbrier Mall

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