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Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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A serene beach scene showcases soft sand and gentle sea grass, with a beautiful sunset illuminating the sky in shades of orange and purple. The calm water reflects the colors, while silhouettes of two people can be seen in the distance near the water's edge.

Guest suite in Virginia Beach

4.9 out of 5 average rating, 645 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.

Guest suite in Chesapeake

4.97 out of 5 average rating, 310 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!

A set of wooden steps leads up to a private entrance, flanked by black wrought iron railings. The area is surfaced with light concrete, and a small outdoor light fixture is mounted near the door, providing visibility in the evening.

Apartment in Portsmouth

4.96 out of 5 average rating, 124 reviews

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

The image captures a serene view of the water at sunset, with vibrant orange and purple hues reflecting on the surface. Soft waves create a gentle ripple effect, while clouds in the sky add dimension to the scene.

Cottage in Norfolk

5 out of 5 average rating, 274 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

Home in Portsmouth

4.94 out of 5 average rating, 115 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, 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!

A disc golf basket stands prominently in a sunny, wooded park area. Tall trees surround the grassy field, casting gentle shadows on the ground. The serene environment suggests a peaceful space for outdoor activities and leisure.

Place to stay in Virginia Beach

4.99 out of 5 average rating, 178 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!

A private backyard pool area is highlighted, featuring a large in-ground pool surrounded by a concrete deck. Lush greenery and trees provide a natural backdrop, while a wooden fence offers privacy. Pool accessories are visible, indicating a space for relaxation and enjoyment.

Guest suite in Chesapeake

4.95 out of 5 average rating, 570 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.

The private room features a spacious bed draped with a textured blanket, accompanied by a cozy armchair and an accent chair. A decorative fireplace is situated under a wall with circular art pieces. Natural light filters through the window, enhancing the room's warm tones.

Apartment in Olde Towne

4.98 out of 5 average rating, 110 reviews

English Basement Hide-Away

Private Suite in the heart of Olde Towne, Portsmouth! This historic English Basement style home has a private street entrance. Walking distance from the the waterfront, restaurants, local shopping, Coast Guard Base and Navy Hospital, Atlantic Union Bank Pavillion, ferry into Downtown Norfolk, The Norva, and the Tides Stadium. 9 minute drive to the Rivers Casino. Quick drive to Military Bases, and approx. a 20 minute drive to VA Beach and a 45 minute drive to Williamsburg/Busch Gardens.

A light-colored countertop features a small tray holding a wrapped soap bar, accompanied by two bottles of toiletries. A matching container with a divided section is also present, enhancing the organized appearance of the bathroom amenities.

Townhouse in Chesapeake

4.89 out of 5 average rating, 147 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

An outdoor space features a shaded patio area with a grill, comfortable red seating, and a dining set. Decorative lights create a festive atmosphere, while an American flag hangs proudly. A lush green lawn and wooden fence frame the scene, enhancing the backyard's privacy.

Guest suite in Chesapeake

4.93 out of 5 average rating, 284 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!

A rustic wooden door with a sliding mechanism is positioned next to a framed sign that reads 'LIVE simply.' A wall-mounted planter holds a small arrangement of greenery, complementing the warm wood tones of the dining chairs and table in the scene.

Apartment in Chesapeake

4.91 out of 5 average rating, 131 reviews

2 BR With King. ⚡️Fast Wifi. 🔐 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.

A vibrant pool scene features two individuals playing volleyball with a pink ball in clear blue water. A slide is visible along the side of the pool, surrounded by well-maintained greenery and a sunny sky above.

Guesthouse in Chesapeake

4.98 out of 5 average rating, 241 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Chesapeake vacation rentals

Dog friendly vacation rentals in Chesapeake

Top guest favorite

A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.

Cottage in East Ocean View

4.98 out of 5 average rating, 255 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

A serene beach scene is presented, featuring gentle waves lapping against the shore. A long pier extends out into the water, framed by grassy dunes on the left. The clear blue sky complements the tranquil coastal atmosphere.

Guest suite in Chic's Beach

4.87 out of 5 average rating, 339 reviews

Virginia Beach 2 King BR apt 100 feet from beach

Top guest favorite

A charming two-story home is seen from the street, featuring a welcoming front porch with white railing. Large windows allow natural light to fill the space. The yard is well-maintained and bordered by a sidewalk, surrounded by trees that provide shade.

Home in Norfolk

4.99 out of 5 average rating, 103 reviews

Ghent on the Corner: Cozy 3 bed 2.5 bath home

The kitchen features modern appliances, including a stainless steel dishwasher and a gas range. White cabinets complement a blue-painted island and patterned tile flooring. Natural light is provided by a window above the sink, enhancing the space's functionality.

Home in Norfolk

4.85 out of 5 average rating, 158 reviews

Picture Worthy Spanish Style Casita! 2 BR/ 2BA

A serene garden is shown, featuring lush greenery and vibrant red foliage from a flowering tree. A stone path winds through the space, leading to a bench nestled among the plants. Subtle details of textures and colors create a tranquil outdoor setting.

Guest suite in Newport News

4.85 out of 5 average rating, 150 reviews

Secret Garden Studio

Top guest favorite

A charming cottage is presented with a well-maintained front yard, featuring blooming trees and vibrant flower planters. A covered porch is visible, framed by decorative railings and welcoming steps that lead from a concrete driveway. The surrounding greenery adds a peaceful ambiance.

Cottage in Norfolk

4.96 out of 5 average rating, 336 reviews

Lovely Ocean View Cottage

Top guest favorite

A charming garden pathway made of red and gray bricks leads to an ornate black gate. Lush greenery, including flower bushes and tall plants, surround the area, creating a tranquil and inviting atmosphere. Natural light filters through the trees, enhancing the serene outdoor space.

Apartment in Portsmouth

4.99 out of 5 average rating, 193 reviews

Elegant Cozy Colonial/Private/Self Check-in

Top guest favorite

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.

4.94 out of 5 average rating, 356 reviews

Sportsman's Paradise ( Hunting & Fishing )

Other great vacation rentals in Chesapeake

An inviting entrance features a pair of large wooden doors with intricate stained glass panels, illuminated by a hanging lantern. A cozy seating arrangement is set beside a planter filled with greenery, welcoming guests to the historic residence.

Guest suite in Downtown Norfolk

4.92 out of 5 average rating, 266 reviews

Cobblestone street apartment with rooftop views!

A brick pathway leads to a white wooden gate, framed by two residential buildings. Green shrubs grow on either side, enhancing the inviting corridor. Utility meters are visible on the walls, providing functional details in this cozy exterior space.

Apartment in Olde Towne

4.82 out of 5 average rating, 102 reviews

Private 1 Bed Apt - Historic Olde Towne Portsmouth

A pathway leads to the beach, bordered by light posts and greenery. A sign indicating 'No Vehicles Beyond This Point' is prominently displayed. The ocean is visible in the background, with soft rays of light breaking through the clouds.

Condo in Virginia Beach

4.89 out of 5 average rating, 217 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Top guest favorite

Apartment in Chesapeake

4.97 out of 5 average rating, 75 reviews

Entire Apartment - No Cleaning Fees!

A spacious living area is defined by a light grey sectional sofa, featuring a yellow and white striped decorative pillow. The open kitchen, equipped with stainless steel appliances, is visible in the background, enhancing the functional layout. Soft natural light illuminates the room through sheer curtains.

Apartment in Chesapeake

4.96 out of 5 average rating, 78 reviews

Blissful Nook @ Washington

Home in East Ocean View

4.92 out of 5 average rating, 194 reviews

@Whit’s End? Come in and Relax

The kitchen features modern stainless steel appliances, including a microwave and an oven. Light-colored cabinets create a bright atmosphere. A dining table with chairs is visible in the background, with wood-like flooring extending throughout the space. Counter space is accentuated by gray speckled countertops.

Townhouse in Chesapeake

4.87 out of 5 average rating, 173 reviews

Tasha's Townhouse *King, Queen, Twin*

A closed white restroom door is displayed, featuring a black sign indicating gender-neutral facilities. The door is situated in a hallway with wooden flooring, providing a clear distinction for guests seeking restroom access.

Home in Chesapeake

4.91 out of 5 average rating, 33 reviews

Comfy House! The Perfect Getaway

Quick stats about vacation rentals in Chesapeake

Total rentals
970 properties
Total number of reviews
32K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
280 properties allow pets
Rentals with a pool
130 properties have a pool
Rentals with dedicated workspaces
510 properties have a dedicated workspace

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 110 vacation rentals in Lynnhaven, over 110 vacation rentals in Salem, over 270 vacation rentals in Ghent, over 500 vacation rentals in Olde Towne, and over 500 vacation rentals in Downtown Norfolk.
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.
How much does it cost to stay in rv rentals in Chesapeake?
Experience the best of Chesapeake with our rv rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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 280 vacation rentals for guests traveling with pets.
What are the most popular amenities for House Rentals in Chesapeake?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a gym, over 120 homes with self check-in, over 100 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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!
Do house rentals in Chesapeake have a bbq area?
Absolutely! We offer over 100 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 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 condo rentals in Chesapeake?
Chesapeake has more than 10 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore