Vacation rentals in Chesapeake

Guest suite in Chesapeake

4.97 out of 5 average rating, 302 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!

4.97 out of 5 average rating, 121 reviews

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

"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.

5 out of 5 average rating, 271 reviews

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

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

Guesthouse in Downtown Norfolk

A modern kitchenette area is highlighted, featuring a compact table with two glasses and a bottle of wine. An air conditioning unit is mounted above, while a small decorative lamp stands on the side. A fire extinguisher is visibly mounted on the wall for safety.

4.98 out of 5 average rating, 625 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.

4.95 out of 5 average rating, 104 reviews

A console table with a wooden top and black metal frame is positioned against a green wall. Above it, a round mirror reflects soft natural light. Four decorative vases adorn the table, complemented by a potted plant and a small lamp on one side.

Home in Chesapeake

The Cozy Cottage Two Bedroom, King bed House

This is a charming and cozy Cape Cod style house. It’s decorations are eclectic and comfortable. There is a king size bed in the master bedroom and a queen size bed in the second bedroom. There are smart TV’s in each bedroom and the living room. This home has brand new central heat and air conditioning, new stainless steel refrigerator and smooth top stove, microwave, and new carpeting. It’s centrally located and there is plenty of space for parking. This is truly a home away from home.

Guest suite in Chesapeake

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.

4.95 out of 5 average rating, 566 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.

4.98 out of 5 average rating, 108 reviews

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

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.

4.86 out of 5 average rating, 177 reviews

A modern kitchen area features a dual-basin sink set into a sleek granite countertop. Marble-patterned backsplash complements the cabinetry, which has gold hardware. Organized kitchen utensils are displayed in a holder, while decorative vessels add a touch of style.

Townhouse in Chesapeake

2BR-1.5 Bath Electric & Vibrant R&R Townhome

Listing description Kick back & relax in this calm, stylish space. 1600 sq ft stunning renovated & designed townhome! -Skip the traffic; 15 min drive to most of Hampton Roads, beaches; 3 mins from restaurants, groceries & more -Free parking -Optimal cleaning 100% disinfected space -2 bedrooms -Comfortable 2 Queen Beds & 1 Full Futon -1.5 baths with high end, modern finishes -Outdoor back private patio seating - Smart home features: keyless access cord + living room TV with roku

4.9 out of 5 average rating, 143 reviews

Townhouse in Chesapeake

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 the home.

Guest suite in Chesapeake

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.

4.93 out of 5 average rating, 281 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!

4.91 out of 5 average rating, 128 reviews

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

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.

4.98 out of 5 average rating, 239 reviews

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

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

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Chesapeake vacation rentals

Laptop-friendly workspace

House rentals in Chesapeake

4.92 out of 5 average rating, 135 reviews

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

3 bedroom private home a block from the beach!

4.91 out of 5 average rating, 110 reviews

A cozy living area features plush grey seating and a contemporary coffee table. A large wall clock is mounted above the sofa, while a sleek recliner sits beside a dark lamp. The open kitchen showcases modern appliances and stylish dark cabinetry.

Home in Buckroe Beach

3 bedroom home minutes from Buckroe Beach

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.

4.94 out of 5 average rating, 114 reviews

Lakefront House @ Oceanfront

4.93 out of 5 average rating, 202 reviews

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

Charming house close to beach and shops!

A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.

4.99 out of 5 average rating, 194 reviews

Play by the Bay 1 MIN TO WATER

A three-story beach house features light-colored wood siding and multiple balconies. Outdoor stairs lead to the upper decks, providing additional space for relaxation. A garage is visible underneath, with a gravel driveway extending to the side, where a fenced area is seen.

4.8 out of 5 average rating, 145 reviews

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

4.91 out of 5 average rating, 128 reviews

A light-colored leather sofa is positioned in a cozy seating area, accompanied by two matching side tables with soft green lamps. A decorative clock is mounted on the wall, and a coffee table with magazines sits in the center, enhancing the inviting space.

Home in Newport News

Relax! Refreshing 3 bedroom Rancher

An aerial view captures the vibrant Croatan Beach, showcasing beachfront homes along the coastline. The ocean presents rolling waves, with soft sandy shores visible. A private pool is discernible among the properties, accentuating the beach community's appeal.

4.86 out of 5 average rating, 134 reviews

Beach Home, Upscale Croatan Resort + Private Pool

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Other great vacation rentals in Chesapeake

4.8 out of 5 average rating, 5 reviews

Condo in Williamsburg

Top choice! Greensprings 4BR/4BA near attractions.

4.84 out of 5 average rating, 283 reviews

A view of the ocean from a living area is presented through sliding glass doors. Natural light fills the space, enhancing the sea view. The patio features a railing and two outdoor chairs, inviting relaxation while taking in the coastal scenery.

Condo in Virginia Beach

Beautiful Beachfront Condo

5 out of 5 average rating, 8 reviews

A high chair in a soft pink hue is positioned against a light grey wall, featuring a plastic tray with a built-in cup holder. The chair is designed for children's comfort and safety.

Home in Newport News

Spacious Family Getaway | 7BR | 3 masters | 5 Bath

4.95 out of 5 average rating, 40 reviews

Home in Norfolk

Family Getaway | 1 Block from Beach | Game Room

Tiny home in Cape Charles

A welcoming porch features a vibrant coral door framed by two windows. Light-colored outdoor chairs are arranged around a small table, complemented by a decorative mat and nautical-inspired decor. The covered area provides a cozy spot to relax outside.

4.89 out of 5 average rating, 124 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

A spacious bedroom features a large bed with fresh linens, complemented by a wooden bench at the foot. Light-colored walls and hardwood floors enhance the airy feel. Natural light floods in through shuttered windows, and bedside lamps provide soft illumination.

4.93 out of 5 average rating, 15 reviews

Incredible Location! Amazing Comfort!

4.95 out of 5 average rating, 101 reviews

A private deck area is presented with dark wicker furniture. Two armchairs and a sofa with light cushions are arranged around a glass-top coffee table. Potted plants are positioned at the corners, contrasting with the wooden decking surface.

Home in Norfolk

Gorgeous Vacation House