TOP 30 Best Vacation rentals in Chesapeake, Virginia

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.

Comfort Suites Chesapeake - Norfolk is a charming lodging institution located at 1550 Crossways Boulevard in Chesapeake, Virginia, United States. This cozy hotel offers spacious and comfortable suites, perfect for both business and leisure travelers. Guests can enjoy amenities such as free Wi-Fi, a complimentary hot breakfast, a fitness center, and an indoor pool. The convenient location provides easy access to nearby attractions and businesses in both Chesapeake and Norfolk. Whether visiting for work or pleasure, Comfort Suites Chesapeake - Norfolk is the ideal choice for a relaxing and enjoyable stay.

Delta Hotels by Marriott Chesapeake Norfolk is a modern and stylish lodging option located at 725 Woodlake Drive in Chesapeake, Virginia, United States. This upscale hotel offers comfortable and well-appointed rooms, a fitness center, a restaurant, and meeting facilities for business travelers. Guests can enjoy the convenience of being located near popular attractions in the Chesapeake and Norfolk area, making it an ideal choice for both leisure and business travelers. With top-notch service and amenities, Delta Hotels by Marriott Chesapeake Norfolk ensures a memorable and enjoyable stay for all guests.

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 Golf Club is a premier golfing destination located at 1201 Club House Drive in Chesapeake, Virginia, United States. Our beautifully landscaped course offers a challenging and enjoyable experience for golfers of all skill levels. With well-maintained fairways, lush greens, and stunning views, Chesapeake Golf Club is the perfect place to tee off and unwind. Our clubhouse provides a welcoming atmosphere where golfers can relax and socialize after a round. Whether you're a seasoned pro or a beginner looking to improve your game, Chesapeake Golf Club is the ideal spot for a day on the links. Come visit us and discover why we are a favorite among golf enthusiasts in the area.

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.

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.

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.

Candlewood Suites Chesapeake/Suffolk, an IHG Hotel, is a comfortable and convenient lodging option located at 4809 Market Place in Chesapeake, Virginia, United States. This modern hotel offers spacious suites equipped with full kitchens, free Wi-Fi, and a 24-hour fitness center. Guests can enjoy a relaxing stay with amenities such as a business center, laundry facilities, and a convenience store. Whether traveling for business or leisure, Candlewood Suites provides a welcoming and home-like environment for guests to enjoy during their stay in Chesapeake/Suffolk.

SpringHill Suites by Marriott Chesapeake Greenbrier is a modern and stylish lodging option located at 1446 Crossways Boulevard in Chesapeake, Virginia, United States. This hotel offers spacious suites with separate living and sleeping areas, as well as convenient amenities such as complimentary breakfast, free Wi-Fi, and a fitness center. Guests can also enjoy the indoor pool and easy access to nearby shopping and dining options. Whether traveling for business or leisure, SpringHill Suites by Marriott Chesapeake Greenbrier provides a comfortable and convenient stay for all guests.

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.

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.

SailTime Chesapeake Bay South is a premier sailing school and store located at 8172 Shore Drive in Norfolk, Virginia, United States. Offering a range of courses and certifications for sailors of all levels, SailTime Chesapeake Bay South is the perfect destination for those looking to improve their sailing skills or start their sailing journey. With experienced instructors and top-of-the-line equipment, students can expect a high-quality learning experience. Additionally, the store offers a variety of sailing gear, equipment, and accessories for purchase, ensuring that sailors are well-equipped for their time on the water. Whether you're a seasoned sailor or a beginner, SailTime Chesapeake Bay South has everything you need to make the most of your sailing adventures.

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.

Tattersall Chesapeake is a premier real estate agency located in the heart of Chesapeake, Virginia. Situated at 504 Cap Stone Arch, our team of experienced and knowledgeable agents are dedicated to helping clients find their dream homes in this beautiful coastal city. Whether you are looking to buy, sell, or rent property in Chesapeake, our agency is here to provide exceptional service and guidance every step of the way. Contact us today to start your real estate journey with Tattersall Chesapeake.

Homewood Suites by Hilton Chesapeake-Greenbrier is a comfortable and welcoming lodging option located at 1569 Crossways Boulevard in Chesapeake, Virginia, United States. This hotel offers spacious suites with separate living and sleeping areas, fully equipped kitchens, and complimentary Wi-Fi. Guests can enjoy a complimentary hot breakfast each morning and unwind in the evening at the evening socials held on select weeknights. The hotel also features a fitness center, indoor pool, and outdoor patio with a fire pit. With its convenient location near shopping, dining, and attractions, Homewood Suites by Hilton Chesapeake-Greenbrier is the perfect choice for both business and leisure travelers.

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.

Chesapeake Campground is a picturesque retreat located at 693 George Washington Highway South in Chesapeake, Virginia, United States. This charming institution offers a range of accommodations, from campsites for tents and RVs to cozy cabins for those seeking a more luxurious stay. Surrounded by lush greenery and peaceful nature, Chesapeake Campground provides a serene and relaxing atmosphere for guests to unwind and connect with the great outdoors. With amenities such as picnic areas, hiking trails, and a playground, this campground is perfect for families, couples, and solo travelers alike. Whether you're looking to escape the hustle and bustle of city life or simply enjoy a weekend getaway, Chesapeake Campground is the ideal destination for a memorable and rejuvenating experience.

Extended Stay America - Chesapeake - Greenbrier Circle is a comfortable and convenient lodging option located at 809 Greenbrier Circle in Chesapeake, Virginia, United States. This institution offers spacious rooms with fully equipped kitchens, free Wi-Fi, and on-site laundry facilities, making it perfect for both short-term and long-term stays. Guests can also enjoy complimentary breakfast and access to a fitness center during their stay. With its convenient location near shopping, dining, and entertainment options, Extended Stay America - Chesapeake - Greenbrier Circle is the ideal choice for travelers looking for a home away from home in Chesapeake.

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.

Extended Stay America - Chesapeake - Churchland Blvd. is a comfortable and convenient lodging option located at 3214 Churchland Boulevard in Chesapeake, Virginia, United States. This institution offers spacious and well-equipped rooms for extended stays, making it ideal for both business travelers and tourists. Guests can enjoy amenities such as fully equipped kitchens, free Wi-Fi, and on-site laundry facilities. The location is also convenient, with easy access to local attractions, dining options, and shopping centers. Whether you're staying for a few nights or a few weeks, Extended Stay America - Chesapeake - Churchland Blvd. provides a home away from home experience.

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.

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.

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.

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.

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.

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.

Chesapeake Bay Properties Inc is a real estate agency located at 850 Brammer Drive in Heathsville, Virginia. Specializing in properties in and around the beautiful Chesapeake Bay area, our team of experienced professionals are dedicated to helping clients find their dream waterfront homes, vacation getaways, or investment properties. With a focus on personalized service and attention to detail, Chesapeake Bay Properties Inc is committed to providing the highest level of customer satisfaction. Contact us today to start your journey towards finding the perfect property in this stunning coastal region.