Holiday rentals in Chesapeake
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Top-rated holiday rentals in Chesapeake
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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!
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.
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!
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.
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.
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 farmsā fire pit in the evening.
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.. Iām positive you will love it!
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.
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, itās a peaceful getaway from city life yet close to beaches, parks, and attractions. From the moment you arrive, youāll feel the warmth and relaxation of a true country home. Itās been a great rental with great ratings.
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!
2 BR With King. ā”ļøFast Wifi. š 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. Brās 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.
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
Other great holiday rentals in Chesapeake
Southern Charm Warm and Welcome
- The Evergreen House -
Portsmouth Waterfront Home | Patio + River Views
The Birdās Nest
Norfolk Beach Bungalow ā¢ Cozy & Convenient
Bayview Cottage II
Hidden Gem.4/bedroom cozy home fenced in yard
Historic Carriage House at the Church Point Manor
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ā¹9,237 | ā¹9,237 | ā¹9,698 | ā¹10,160 | ā¹10,622 | ā¹10,807 | ā¹11,269 | ā¹11,084 | ā¹9,883 | ā¹10,068 | ā¹10,160 | ā¹10,253 |
| Avg. temp | 6Ā°C | 7Ā°C | 10Ā°C | 16Ā°C | 20Ā°C | 25Ā°C | 27Ā°C | 26Ā°C | 23Ā°C | 18Ā°C | 12Ā°C | 8Ā°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 childrenās 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 Arboretumās 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 34ā51Ā°F (1ā10Ā°C) with regular rainfall, and summers near 73ā89Ā°F (23ā32Ā°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 55ā77Ā°F (13ā25Ā°C), and the cityās 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 childrenās 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 cityās 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 ā¹924 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
Chesapeakeās top spots include Chrysler Museum of Art, Nauticus and Cinema Cafe-Greenbrier Mall
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Water Country USA
- Buckroe Beach
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Town Point Park
- Nauticus
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Currituck Beach Lighthouse
- Currituck Beach