The 30 Best Vacation rentals in Chesapeake, Virginia

Escape to a picturesque River Retreat vacation rental nestled in the stunning Chesapeake Bay area. This idyllic property is located at 150 East Harbor Drive in Reedville, Virginia, offering a peaceful and serene getaway for travelers seeking relaxation and tranquility. Managed by a reputable real estate and travel agency, this retreat is the perfect destination for those looking to unwind and reconnect with nature. With breathtaking views of the river and luxurious amenities, guests can enjoy a truly unforgettable experience. Book your stay today and immerse yourself in the beauty of the Chesapeake Bay.

Chesapeake Bay Campground is a picturesque retreat located at 382 Campground Road in Reedville, Virginia. Nestled along the stunning shores of the Chesapeake Bay, this institution offers a variety of accommodations including tent and RV sites, cozy cabins, and comfortable lodges. Guests can enjoy the beauty of nature in this peaceful park setting, with amenities such as hiking trails, fishing spots, and picnic areas. Whether you're looking for a relaxing getaway or a fun-filled outdoor adventure, Chesapeake Bay Campground has something for everyone. Come and experience the beauty of the Bay at this charming retreat in Virginia.

Cape Charles / Chesapeake Bay KOA Resort is a picturesque campground and lodging destination situated in the charming town of Cape Charles, Virginia. Located on the scenic Charles M Lankford Junior Memorial Highway, this resort offers a peaceful retreat for visitors looking to explore the beauty of the Chesapeake Bay area. With spacious RV sites, cozy cabins, and tent camping options available, Cape Charles / Chesapeake Bay KOA Resort caters to a variety of travelers seeking a relaxing outdoor getaway. Guests can enjoy amenities such as a swimming pool, playground, and outdoor recreational activities, making it the perfect destination for families, couples, and solo adventurers alike.

InTown Suites Extended Stay Chesapeake VA – I-64/Crossways Blvd offers newly renovated extended stay suites in Chesapeake, Virginia. With added amenities and comforts, our suites provide a home away from home experience. Each suite features HDTVs with premium channels, custom mattresses, and storage options such as built-in closets and bathroom vanities. Choose from Premium, Upgraded, or Traditional suite options to fit your budget. Enjoy the convenience of a fully furnished in-room kitchen, super-fast Wi-Fi, and friendly service. Check-in is at 3:00 p.m. and check-out is at 12:00 p.m. No pets allowed. Welcome to your comfortable and affordable extended stay at InTown Suites Chesapeake VA – I-64/Crossways Blvd.

Sleep Inn & Suites Chesapeake - Portsmouth is a cozy and comfortable lodging option located at 3280 Western Branch Boulevard in Chesapeake, Virginia, United States. With a convenient location near Portsmouth and easy access to major highways, this hotel is a perfect choice for both business and leisure travelers. The modern rooms and suites offer a relaxing atmosphere, and amenities such as free Wi-Fi, a complimentary breakfast, and a fitness center make for a pleasant stay. Whether you are visiting for work or pleasure, Sleep Inn & Suites Chesapeake - Portsmouth provides a welcoming and enjoyable experience for all guests.

Holiday Inn Express & Suites Chesapeake is a cozy and comfortable lodging option located at 2436 Gum Road in Chesapeake, Virginia, United States. As an IHG Hotel, guests can expect top-notch service and modern amenities during their stay. The hotel offers spacious rooms and suites, complimentary breakfast, a fitness center, and a business center for guests on the go. Whether traveling for business or pleasure, Holiday Inn Express & Suites Chesapeake is the perfect choice for a relaxing and convenient stay.

TownePlace Suites by Marriott Suffolk Chesapeake is a charming lodging institution located at 8050 Harbour View Boulevard in Suffolk, Virginia, United States. This cozy hotel offers spacious and well-appointed suites for guests looking for a comfortable stay in the area. The hotel is conveniently situated near Chesapeake, providing easy access to local attractions, shopping, and dining options. Guests can enjoy amenities such as complimentary breakfast, a fitness center, and a relaxing outdoor pool. Whether visiting for business or leisure, TownePlace Suites by Marriott Suffolk Chesapeake is the perfect choice for a relaxing and enjoyable stay.

Days Inn by Wyndham Chesapeake is a comfortable and affordable lodging option located at 1439 George Washington Highway North in Chesapeake, Virginia. This hotel offers spacious and well-appointed rooms, complimentary breakfast, free Wi-Fi, and a seasonal outdoor pool for guests to enjoy. Conveniently situated near local attractions and shopping areas, Days Inn by Wyndham Chesapeake is the perfect choice for both business and leisure travelers looking for a relaxing stay in the heart of Virginia.

Wingate by Wyndham Chesapeake is a comfortable and convenient lodging option located at 817 Greenbrier Circle in Chesapeake, Virginia, United States. This hotel offers spacious rooms, modern amenities, and friendly service to ensure a pleasant stay for guests. Whether you are traveling for business or leisure, Wingate by Wyndham Chesapeake provides a relaxing atmosphere for a restful night's sleep. With its convenient location near shopping, dining, and entertainment options, this hotel is the perfect choice for your stay in Chesapeake.

Hyatt Place Chesapeake/Greenbrier is a modern and stylish lodging option located at 709 Eden Way North in Chesapeake, Virginia. Situated in the bustling Greenbrier area, this hotel offers a convenient and comfortable stay for both business and leisure travelers. The spacious rooms are well-appointed with contemporary amenities, including plush bedding, flat-screen TVs, and free Wi-Fi. Guests can also enjoy a complimentary breakfast each morning and access to the on-site fitness center and outdoor pool. With its central location and top-notch services, Hyatt Place Chesapeake/Greenbrier is the perfect choice for a relaxing stay in the heart of Chesapeake.

Hilton Garden Inn Chesapeake/Suffolk is a charming lodging institution situated at 5921 Harbour View Boulevard in Suffolk, Virginia, United States. This cozy hotel offers comfortable accommodations and top-notch amenities for both leisure and business travelers. Guests can enjoy spacious rooms, a fitness center, a restaurant, and a convenient location near popular attractions. Whether you're visiting for a weekend getaway or a work trip, Hilton Garden Inn Chesapeake/Suffolk provides a welcoming and relaxing atmosphere for all guests.

Bowers Hill Inn Chesapeake is a charming lodging establishment located at 4725 West Military Highway in Chesapeake, Virginia, United States. This cozy inn offers comfortable accommodations and a warm, welcoming atmosphere for guests to relax and unwind. With convenient access to nearby attractions and amenities, Bowers Hill Inn Chesapeake is the perfect choice for travelers looking for a peaceful and enjoyable stay in the heart of Chesapeake.

WoodSpring Suites Chesapeake-Norfolk Greenbrier is a comfortable and convenient lodging option located at 1708 Sentinel Drive in Chesapeake, Virginia, United States. This extended-stay hotel offers spacious and well-equipped rooms for guests looking for a home away from home. With a focus on providing a clean and comfortable environment, WoodSpring Suites is the perfect choice for travelers in need of a long-term stay in the Chesapeake-Norfolk area. Enjoy the convenient location near shopping, dining, and entertainment options, making it easy to explore all that the area has to offer.

Savannah Suites Chesapeake is a comfortable and convenient lodging option located at 1409 Tintern Street in Chesapeake, Virginia. This institution offers spacious suites with modern amenities, perfect for both short and long-term stays. Guests can enjoy a complimentary breakfast, free Wi-Fi, and a fitness center. The friendly staff is dedicated to providing excellent service to ensure a pleasant and memorable stay for all visitors. Located in a prime location in Chesapeake, guests can easily access nearby attractions, restaurants, and shopping centers. Experience a relaxing and enjoyable stay at Savannah Suites Chesapeake.

Staybridge Suites Chesapeake - Virginia Beach, an IHG Hotel, is a welcoming and comfortable lodging option located at 709 Woodlake Drive in Chesapeake, Virginia. Situated just a short drive away from the vibrant city of Virginia Beach, this hotel offers spacious suites equipped with modern amenities for a relaxing stay. Guests can enjoy complimentary breakfast, a fitness center, an outdoor pool, and a business center during their stay. Whether visiting for business or leisure, Staybridge Suites Chesapeake - Virginia Beach provides a convenient and enjoyable accommodation option in the heart of Virginia.

Fairfield Inn & Suites by Marriott Chesapeake is a comfortable and convenient lodging option located at 1560 Crossways Boulevard in Chesapeake, Virginia, United States. The hotel offers a range of amenities including a complimentary breakfast, free Wi-Fi, a fitness center, and an indoor pool. The rooms are spacious and well-equipped with modern furnishings, making it a perfect choice for both business and leisure travelers. The friendly staff at Fairfield Inn & Suites by Marriott Chesapeake are dedicated to providing guests with a pleasant and enjoyable stay.

Courtyard by Marriott Chesapeake Greenbrier is a stylish and modern lodging establishment located at 1562 Crossways Boulevard in Chesapeake, Virginia, United States. This hotel offers comfortable and well-appointed rooms, a fitness center, an indoor swimming pool, and a convenient location near shopping and dining options. Guests can enjoy a relaxing stay with excellent amenities and exceptional service at Courtyard by Marriott Chesapeake Greenbrier.

Extended Stay America - Chesapeake - Crossways Blvd. is a comfortable and convenient lodging option located at 1540 Crossways Boulevard in Chesapeake, Virginia, United States. This hotel offers spacious and well-equipped rooms with amenities such as fully equipped kitchens, free Wi-Fi, and flat-screen TVs. Perfect for both short and long-term stays, guests can enjoy a complimentary grab-and-go breakfast and access to on-site laundry facilities. The hotel's location provides easy access to nearby attractions, restaurants, and businesses, making it an ideal choice for travelers visiting the area for work or leisure.

Located in the heart of Chesapeake, Virginia, the Residence Inn by Marriott Chesapeake Greenbrier offers modern and comfortable lodging for both short and extended stays. The hotel boasts spacious suites with fully equipped kitchens, complimentary breakfast, free Wi-Fi, and a fitness center. Guests can relax in the outdoor pool or enjoy a BBQ in the picnic area. Situated near shopping, dining, and entertainment options, this hotel is the perfect choice for business travelers and vacationers alike.

InTown Suites Extended Stay Chesapeake VA – Greenbrier Road offers newly renovated weekly rentals on Greenbrier Road in Chesapeake, Virginia. Our premium suites feature brand new kitchens, appliances, cabinets, and HDTVs with premium channels like SHOWTIME. Each suite is set up like a studio apartment, providing a comfortable and convenient stay. With three suite options to choose from, including Premium, Upgraded, and Traditional, there is something to fit every budget. Our location is close to I-64, making it easy to access the surrounding area. Guests will enjoy amenities such as weekly housekeeping, super-fast Wi-Fi, and HD programming. Make yourself at home at InTown Suites Chesapeake VA – Greenbrier Road and experience the best of extended stay lodging.

Chesapeake Properties is a reputable real estate and travel agency located at 7 Fig Street in the charming town of Cape Charles, Virginia, United States. With a team of experienced professionals, Chesapeake Properties specializes in helping clients find their dream homes or vacation rentals in this beautiful coastal community. Whether you are looking to buy, sell, or rent property, their dedicated staff is committed to providing personalized service to meet your unique needs. Contact Chesapeake Properties today to start your journey towards finding the perfect property in Cape Charles.

Chesapeake Dream is a charming lodging, real estate, and travel agency located at 101 Tazewell Avenue in Cape Charles, Virginia, United States. This restored three-story Victorian Four Square built in 1912 is only four houses away from the beach, making it the perfect destination for a relaxing getaway. With 4 bedrooms, 3 1/2 baths, and sleeping accommodations for up to 11 people, Chesapeake Dream offers a spacious and comfortable stay. Enjoy modern amenities such as WiFi, three televisions, a large kitchen with top-of-the-line appliances, and central heat and air conditioning. The property also features a wrap-around porch with rockers, outdoor shower, charcoal grill, and beautiful gardens. Located in the historic town of Cape Charles, guests can explore the pedestrian-friendly streets lined with historic homes and large shade trees. The town offers a variety of activities, including swimming, sunbathing, golfing, shopping, dining, and exploring nearby state parks and museums. From the 4th of July celebrations to visits from Tall Ships, there is always something exciting happening in Cape Charles.

YOLO Travel and Vacations LLC is a premier travel agency located at 852 Greenfield Lane, Chesapeake, Virginia, United States. Our dedicated team of travel experts is committed to providing exceptional service and personalized experiences for our clients. Whether you're looking for a relaxing beach getaway, an adventurous safari, or a romantic European vacation, we have you covered. Let us take the stress out of planning your next trip so you can focus on creating unforgettable memories. Contact us today to start planning your dream vacation with YOLO Travel and Vacations LLC.

Blue Crab Cottage is a charming lodging establishment located at 211 Vernon Street in the quaint town of Colonial Beach, Virginia. This cozy cottage offers a serene and comfortable retreat for guests looking to relax and unwind by the beautiful Chesapeake Bay. The Blue Crab Cottage is tastefully decorated in a coastal theme, with modern amenities and a touch of Southern hospitality. Perfect for a weekend getaway or a longer stay, this institution is the perfect escape for those looking to enjoy the beauty of Virginia's waterfront.

The Haven On The Bay is a real estate and travel agency located at 160 Shipwatch Lane, Reedville, Virginia, United States. Find your perfect vacation rental free of service fees with us. From oceanfront condos with free beach lounges to secluded cabins with stunning Blue Ridge Mountains views, we have a wide range of properties to choose from. Our beautifully renovated and newly furnished vacation villas offer everything you need for a relaxing getaway. Whether you prefer to be near the beach or surrounded by the tranquility of the North Georgia mountains, we have the perfect rental for you. Houfy, our advertising platform, offers over 60,000 vacation rentals worldwide with no booking or service fees. Guests and hosts can save money by booking directly through Houfy. Easily search for and book a property with a Houfy host anywhere in the world.

Tangier Island Cruises, located at 468 Buzzards Point Road in Reedville, Virginia, offers unforgettable trips to Tangier Island and the Chesapeake Bay. Departing from the historic fishing town of Reedville, visitors can enjoy a cruise across the bay to Tangier Island, where they can savor the freshest seafood and explore the hidden gems of this Virginia Historic Landmark. With a focus on providing fun for all ages and catering to large groups, Tangier Island Cruises has been family-owned and operated since 1970. In addition to daily ferry trips to Tangier Island, they also offer evening and sunset cruises for those seeking a more unique experience on the water.

Located at 16650 Hog Ridge Road in Tangier, Virginia, the Brigadune Inn offers a peaceful retreat from the hustle and bustle of daily life. Owned and managed by Barb & Rob Baechtel, this charming property overlooks the Chesapeake Bay and provides a serene setting for guests to relax and unwind. The Inn is just a short walk away from a nearly deserted beach, where guests can enjoy a leisurely stroll or watch a breathtaking sunset over the water. The name "Brigadune" is a nod to the timeless history of the island and the close-knit community that calls it home.

Bay View Inn B&B is a charming bed and breakfast located at 16408 West Ridge Road in Tangier, Virginia. Situated in a picturesque location with stunning views of the bay, this cozy inn offers a peaceful retreat for guests looking to relax and unwind. The rooms are beautifully decorated and equipped with all the amenities needed for a comfortable stay. Guests can enjoy a delicious homemade breakfast in the morning and explore the nearby attractions such as Tangier Island and the Chesapeake Bay. Whether you are looking for a romantic getaway or a family vacation, Bay View Inn B&B is the perfect choice for your lodging needs.

Reedville Landing is a charming waterfront institution located at 284 Morris Avenue in Reedville, Virginia. Situated in the heart of the historic town, Reedville Landing offers a picturesque setting overlooking the tranquil waters of the Chesapeake Bay. Visitors can enjoy fresh seafood, local cuisine, and a variety of dining options while taking in the stunning views of the marina and surrounding area. With its welcoming atmosphere and scenic location, Reedville Landing is the perfect destination for a relaxing meal or special event.

J&J Limousine Service is a premier car rental institution located at 135 Tilden Avenue in Chesapeake, Virginia. We offer top-of-the-line limousines for all your transportation needs, whether it be for a special event, business meeting, or airport transfer. Our fleet of luxury vehicles is meticulously maintained and our professional chauffeurs are dedicated to providing a safe and comfortable ride for our clients. Experience the ultimate in luxury transportation with J&J Limousine Service.