Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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

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Top guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 693 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 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
4.96 out of 5 average rating, 348 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 bright sleeping area features a spacious bed with light blankets, accented by a decorative throw. A large circular window allows natural light to fill the space, complemented by dark curtains. A cozy armchair sits nearby, enhancing the room's inviting ambiance.
Guest house in Ghent
4.97 out of 5 average rating, 671 reviews

Private Guesthouse, Ghent/Downtown near ODU, EVMS

Legally licensed and permitted with the City of Norfolk! We did it right here! European-style guesthouse between Ghent and the Heart of Downtown. Walking access to many restaurants and hotspots, and across from “The Tide” light rail, and YMCA, Chrysler Museum of Art, Granby St, Colley Ave, EVMS, Town Point Park! 15-min from the ocean. FREE PRIVATE PARKING: designated driveway parking spot; Kitchenette includes– cooktop, sink, microwave, coffee, fridge; Wifi, separate HVAC, bath, FREE laundry.

Top guest favourite
A spacious guest suite features a large bed with layered bedding, accompanied by a cozy green throw. A vibrant area rug enhances the room's warmth, while a small table and chair provide a work or relaxation space. A kitchenette area is visible in the background.
Place to stay in Virginia Beach
4.99 out of 5 average rating, 206 reviews

Salty Willow-a “suite retreat” in the heart of VB!

We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

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, 173 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 Chesapeake
4.95 out of 5 average rating, 610 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 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
4.9 out of 5 average rating, 164 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

Guest favourite
A light-filled living space features a comfortable leather sofa and a modern dining table. A TV is mounted on the wall, and a large window allows natural light to illuminate the room. A small indoor plant adds a touch of greenery, enhancing the airy ambiance.
Flat in Chesapeake
4.97 out of 5 average rating, 30 reviews

Serene Tree House Retreat | Spacious 1br/1bth Home

Step inside a tucked-away hidden oasis surrounded by trees and waterfront views. The apt is on the 2nd floor amongst the trees. One of the trees is a 200-year-old Magnolia Tree, which is why the space is called Magnolia Tree House. The tall windows make the space bright and airy and give you a 180-degree scenic view of the treetops. To bring the outside in, we decorated the apt to feel like the trees are also inside. The cozy furnishings will make it hard to leave.

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, 100 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 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.
Guest house in Chesapeake
4.89 out of 5 average rating, 94 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!

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!

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?

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Avg. price₹8,998₹8,998₹9,448₹9,898₹10,348₹10,527₹10,977₹10,797₹9,628₹8,998₹8,998₹8,998
Avg. temp6°C7°C10°C16°C20°C25°C27°C26°C23°C18°C12°C8°C

Frequently Asked Questions

  • Where should I stay in Chesapeake?

    Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 270 vacation rentals in Ghent, over 110 vacation rentals in Salem, and over 100 vacation rentals in Lynnhaven.

  • Are there vacation rentals with a dedicated workspace in Chesapeake?

    Yes! Work meets play with ease at over 510 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chesapeake?

    Four-legged friends are welcome in Chesapeake. Choose from more than 300 vacation rentals for guests traveling with pets.

  • Are there Chesapeake vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 130 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in private suite rentals in Chesapeake?

    Experience the best of Chesapeake with our private suite rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chesapeake have a bbq area?

    Absolutely! We offer over 110 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do townhouse rentals in Chesapeake have a gym?

    Absolutely! We offer over 10 townhouse rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Chesapeake have wifi?

    Absolutely! We offer over 150 apartment rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Chesapeake have self check-in?

    Absolutely! We offer over 10 condo rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Chesapeake?

    Chesapeake has more than 50 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Quick stats about holiday rentals in Chesapeake

  • Total holiday rentals

    Explore 970 holiday rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake holiday rentals start at ₹900 per night before taxes and fees

  • Verified guest reviews

    Over 35,620 verified reviews to help you choose

  • Family-friendly holiday rentals

    440 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

    510 properties have a dedicated workspace

  • Wifi availability

    930 of Chesapeake holiday rentals include wifi 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 Cinemark Chesapeake Square

Destinations to explore

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