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Chesapeake vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesapeake vacation rentals

Self check-in
Hot tub
Monthly stays
Gym
BBQ grill

Stay near Chesapeake's top sights

Waterside20 locals recommend
Chrysler Museum of Art184 locals recommend
Nauticus162 locals recommend
MacArthur Center153 locals recommend
Waterside District143 locals recommend
Topgolf111 locals recommend

Vacation rentals with jacuzzis in Chesapeake

Superhost
A welcoming entrance to a brick building is framed by lush greenery and colorful flower beds. The image features the American flag waving gently in the breeze, complemented by a well-maintained pathway leading to the main entryway.
Condo in Williamsburg
5 out of 5 average rating, 3 reviews

The Historic Powhatan Resort 1BD

Superhost
The resort building features a harmonious blend of brick and siding, showcasing large windows and a welcoming entrance. Lush greenery and manicured landscaping enhance the exterior, complemented by a clear blue sky above.
Apartment in Williamsburg
4.95 out of 5 average rating, 39 reviews

Greensprings Resort- 4 bedrooms sleeps 12

Top guest favorite
A private Jacuzzi is positioned on a covered porch, surrounded by greenery. LED lights illuminate the water, creating a relaxing atmosphere, while a ceiling fan provides airflow. Adjacent to the hot tub, a clock is mounted on the wall, enhancing the outdoor space.
Guesthouse in Portsmouth
4.97 out of 5 average rating, 196 reviews

Spring Hill Guest Cottage - Portsmouth

Superhost
A spacious bedroom features a light blue accent wall and a large white bed with a decorative throw blanket. On either side of the bed, stylish lamps provide soft lighting, and a colorful pillow adds a subtle pop of color.
Apartment in Williamsburg
5 out of 5 average rating, 3 reviews

Williamsburg King's Creek Plantation 1BR, 1BA Unit

Superhost
The Ocean Key Resort building stands prominently against a sunset backdrop, highlighting its multiple stories and modern architectural design. The beach is visible across the street, with surroundings including nearby roads and structures, emphasizing the resort's convenient location.
Apartment in Virginia Beach
4.8 out of 5 average rating, 5 reviews

Ocean Key Resort 1 bedroom with balcony!

Superhost
The exterior of a two-story condo building is shown, featuring a combination of light grey and brick siding. Windows are prominently displayed, with vibrant green shutters and red doors adding color to the curb appeal. Lush landscaping surrounds the entrance, enhancing the inviting atmosphere.
Condo in Williamsburg
4.67 out of 5 average rating, 6 reviews

Greensprings Vacation Resort- 2 bedroom

Guest favorite
A wide, sandy beach is outlined by spacious condos in soft pastel colors against a clear blue sky. Fishing rods are positioned in the sand near beach carts, indicating a relaxed atmosphere. Waves gently lap at the shoreline, creating a tranquil coastal setting.
Condo in Sandbridge
4.87 out of 5 average rating, 232 reviews

Ocean Escape

Guest favorite
A charming log cabin features a front porch with a wooden railing and seating area. Surrounding the cabin are landscaped flower beds, tall trees, and a well-kept lawn. The cabin's rustic design is complemented by its natural setting, offering a peaceful view of the waterfront.
Cabin in Smithfield
4.89 out of 5 average rating, 140 reviews

Wickline Cabin on Moon Creek

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House rentals in Chesapeake

Guest favorite
A spacious living room features a comfortable sectional sofa, a wooden entertainment center with a large TV, and a decorative console table. Light-colored walls complement the area rug, and framed artwork adds interest. A staircase is visible, leading to the upper level.
Home in Norfolk
4.92 out of 5 average rating, 131 reviews

3 bedroom private home a block from the beach!

Guest favorite
Home in Buckroe Beach
4.91 out of 5 average rating, 109 reviews

3 bedroom home minutes from Buckroe Beach

Guest favorite
An open and inviting living area features two sofas in blue and gray, complemented by a light wooden coffee table. Natural light filters through large windows, highlighting the subtle wall art and a mix of seating options including stylish chairs and a lamp.
Home in Virginia Beach
4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

Guest favorite
The covered porch features a seating area with two white chairs and a small table, surrounded by hanging flower baskets. The front door is framed by large windows, allowing natural light into the space. Lush trees are visible in the background.
Home in Moyock
4.86 out of 5 average rating, 113 reviews

Cozy Country Cottage

Guest favorite
A charming two-story beach house is presented with yellow siding and blue shutters. A white picket fence surrounds the front yard, while fish-shaped decorations adorn the exterior. A welcoming porch features a green front door, inviting guests to relax in the coastal atmosphere.
Home in Cape Charles
4.93 out of 5 average rating, 201 reviews

Charming house close to beach and shops!

Top guest favorite
A cozy living room is featured, showcasing a light-colored sofa paired with two yellow accent chairs. A wooden coffee table sits at the center, and two windows are dressed with sheer curtains, allowing gentle light to brighten the space. A ceiling fan is present above.
Home in Chesapeake
4.95 out of 5 average rating, 103 reviews

The Cozy Cottage Two Bedroom, King bed House

Top guest favorite
The exterior view of the beach home showcases a charming two-story structure with a shingle facade. A well-maintained pathway leads to the entrance, surrounded by landscaped plants and a spacious driveway accommodating two vehicles. A deck is visible above, offering potential outdoor relaxation areas.
Home in Virginia Beach
4.99 out of 5 average rating, 190 reviews

Play by the Bay 1 MIN TO WATER

Superhost
A balcony area features two brightly colored chairs, one blue and one red, positioned on a wooden deck. The view includes tree-lined surroundings and a quiet street, emphasizing a tranquil outdoor space.
Home in Virginia Beach
4.8 out of 5 average rating, 145 reviews

Chesapeake Bay Beach house (Chic’s Beach) 1 block!

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House rentals with jacuzzis in Chesapeake

Top guest favorite
An outdoor gathering space is illuminated by string lights, featuring a fire pit surrounded by several black adirondack chairs. The two-story blue house looms in the background, showcasing multiple balconies and steps leading to the lower level.
Home in Corolla
5 out of 5 average rating, 17 reviews

*May specials LUX, Firepit pool/hot tub,ocean view

Guest favorite
Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.
Home in Portsmouth
4.94 out of 5 average rating, 107 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Guest favorite
A four-person hot tub is illuminated with blue light, set within a cozy space featuring string lights overhead. Large windows with decorative shutters provide natural light, while a comfortable swing chair is positioned nearby, enhancing the relaxation area.
Home in Newport News
4.92 out of 5 average rating, 75 reviews

1-Bedroom Home Near Christopher Newport University

Guest favorite
A shaded deck area features two wooden rocking chairs with blue cushions and a small side table. Large windows are visible in the background, allowing natural light to brighten the space. The expansive wooden flooring complements the tranquil atmosphere.
Home in Corolla
5 out of 5 average rating, 16 reviews

Lazy Palm Carova 4x4 Beach

Superhost
A hot tub is enclosed within a shaded gazebo, illuminated by soft lights. The surrounding fence adds privacy, while the serene blue water invites relaxation. The evening setting creates a calming atmosphere, perfect for unwinding after a day of activities.
Home in Buckroe Beach
4.87 out of 5 average rating, 39 reviews

Baybreeze @ Buckroe -hot tub, sauna, game rm. 5bd

Guest favorite
The image showcases a bayfront retreat with a spacious outdoor area featuring a private pool surrounded by lounge chairs. A wooden deck extends into the water, providing access to the private dock. Lush landscaping and trees frame the view, with a two-story house in the background.
Home in Sandbridge
5 out of 5 average rating, 7 reviews

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

Superhost
A deck overlooks the tranquil waterway, with picturesque views of grassy areas and the shoreline. Brightly colored chairs provide seating options, while a wooden railing frames the outdoor space. The clear blue sky enhances the inviting atmosphere.
Home in Cape Charles
4.67 out of 5 average rating, 3 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Guest favorite
A spacious hot tub is situated on the deck, overlooking the vast expanse of the water. The tranquil surface ripples under the cloudy sky, creating a serene ambiance. A black lounge chair is positioned nearby, inviting relaxation while enjoying the captivating views.
Home in Buckroe Beach
4.96 out of 5 average rating, 77 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

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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 500 vacation rentals in Olde Towne, over 110 vacation rentals in Salem, over 270 vacation rentals in Ghent, 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.

  • 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.

  • 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 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.

  • Do apartment rentals in Chesapeake have a bbq area?

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

  • Do house rentals in Chesapeake have a gym?

    Absolutely! We offer over 60 house rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

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

    Absolutely! We offer over 40 apartment rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Chesapeake?

    Chesapeake has more than 440 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Apartment Rentals in Chesapeake?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with a gym, over 10 homes with a bbq area, over 40 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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