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Holiday houses in Chesapeake

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Quick stats about holiday rentals in Chesapeake

  • Total holiday rentals

    Explore 950 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 37,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 280 rentals that welcome pets

  • Holiday rentals with a pool

    120 properties feature pools

  • Rentals with dedicated workspaces

    480 properties have a dedicated workspace

  • Wi-Fi availability

    890 of Chesapeake holiday 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 holiday rentals in Chesapeake

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

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Guest favourite
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, 172 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!

FamilyValueWi-Fi

Superhost
A comfortable living room area is featured, showcasing a light-colored sectional sofa with dark blue accent pillows. A dark coffee table is set in front of the sofa. A vibrant world map painting adorns the wall, and natural light streams through a nearby window.
Guest suite in Portsmouth
4.96 out of 5 average rating, 122 reviews

Historic Hideaway Private Apartment/Suite

You will be comfortable in this spacious, one bedroom suite. You have your own kitchen, washer/dryer, and living room space with large tvs in the bedroom and the living room. To wind down from your day step into your large beautiful shower that has endless hot water. Try living room sofa pulls out to a sleeper lay down while watching tv, or to use as an extra bed. Enter/exit thru a private entrance. Only you will have access to your space. Clean and inviting. Stay a day, or stay a while!

LocationValueOutdoor spaces

Guest favourite
A comfortable living room is highlighted by a neutral color palette and natural light streaming through the large windows. Seating arrangements include a cozy sofa, two accent chairs, and a stylish coffee table, with a stone fireplace adding warmth to the space.
Home in Chesapeake
4.9 out of 5 average rating, 67 reviews

Oasis at the Creek| Park, Family & Pet Friendly

Dive into Your Oasis in Deep Creek! Welcome to our 3-bedroom, 2-bath home where the vibes are as laid back as your morning stroll around the neighborhood. Perfect for families, friends, business travelers, or anyone looking to trade city hustle for a serene time. Our home is your ticket to sun-soaked fun and easy commute to local attractions. Located 25-minutes from the local airport, less than 5-minutes from fine dining and local fun. Bring the whole family. Can't wait to host you!

FamilyValueQuiet

Top Guest favourite
A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.
Home in Moyock
4.94 out of 5 average rating, 399 reviews

Sportsman's Paradise ( Hunting & Fishing )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

FamilyValueBeach

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.
Apartment in Chesapeake
4.98 out of 5 average rating, 121 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.

ValueLocationWi-Fi

Guest favourite
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, 190 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

LocationValueWalkability

Guest favourite
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 Chesapeake
4.92 out of 5 average rating, 129 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!

LocationFamilyNearby

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
4.96 out of 5 average rating, 140 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.

FamilyLocationBeach

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 Chesapeake
4.97 out of 5 average rating, 389 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. 💜

ValueFamilyTV

Top Guest favourite
The living area is designed with a mix of modern furnishings and artwork. A comfortable sectional sofa and an accent chair surround a coffee table. Light streams in through a window, highlighting a TV and a decorative cabinet. Artwork adds a pop of color to the neutral walls.
Home in Norfolk
4.93 out of 5 average rating, 148 reviews

3BR Mid-Century Modern Home • Near Airport

Welcome to our beautifully updated 3-bed, 2-bath home in Norfolk. Featuring a spacious layout with cozy beds, it’s ideal for families or groups. Enjoy a gourmet kitchen, a huge dining space, Wi-Fi, a washer and dryer, and all the amenities needed for a relaxing stay. Located next to Norfolk Airport and the Botanic Gardens, you’ll have easy access to all of Hampton Roads. Book your extended getaway today!

LocationValueSleep quality

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 Chesapeake
4.94 out of 5 average rating, 669 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.

LocationValueHeating

Guest favourite
Home in Chesapeake
4.91 out of 5 average rating, 85 reviews

Comfy House! The Perfect Getaway

Bring the whole family to this great place with lots of room for fun! This spacious 4 bedrooms , 2-bathroom home is the perfect blend of comfort and style, offering a relaxing escape for families, groups, or anyone looking for a peaceful retreat. Whether you're here for a short getaway or an extended stay, you'll find everything you need to make your time unforgettable.

ValueLocationDecor

Popular amenities for Chesapeake holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Chesapeake's top sights

Nauticus

252 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 holiday rentals in Chesapeake

Guest favourite
Condo in Chesapeake
4.89 out of 5 average rating, 9 reviews

Entire apartment in Chesapeake, Virginia

LocationAmenitiesHospitality

Top Guest favourite
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.
Home in Chesapeake
4.93 out of 5 average rating, 69 reviews

Spacious 3 Bedroom Home | Near many Shops & Dining

LocationValueQuiet

Top Guest favourite
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
4.9 out of 5 average rating, 63 reviews

The Bird’s Nest

FamilyValueQuiet

Guest favourite
An inviting interior features a spacious bed adorned with soft bedding and decorative pillows. Natural light filters through large windows, illuminating the cozy sitting area with comfortable chairs and a wooden coffee table. Artwork and decorative accents add charm to the welcoming atmosphere.
Guesthouse in Suffolk
4.91 out of 5 average rating, 45 reviews

The Harlequin Cottage

LocationViewComfort

Top Guest favourite
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, 64 reviews

Quiet 3/2 beautiful Chesapeake

ValueLocationBathroom

Guest favourite
A spacious living area features a dark leather sectional sofa adorned with light blue and patterned cushions. A glass coffee table sits at the center, complemented by an area rug with subtle patterns. Natural light enters through the nearby doorway, creating a welcoming environment.
Townhouse in Chesapeake
4.85 out of 5 average rating, 62 reviews

Best Temporary Rental in Chesapeake

ValueFamilyCheck-in

Guest favourite
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
4.89 out of 5 average rating, 36 reviews

Cowbell Cottage

LocationValueBackyard

Home in Virginia Beach
4.93 out of 5 average rating, 15 reviews

Centrally located 2-bedroom Townhouse

LocationFamilyNearby

When is the best time to visit Chesapeake?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$177 NZD$173 NZD$177 NZD$192 NZD$204 NZD$219 NZD$207 NZD$204 NZD$182 NZD$185 NZD$187 NZD$189 NZD
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