Best Holiday rentals and Airbnb offers in Chesapeake, VA
9.7 35 reviews
Chesapeake, VA
01/12 – 29/12
SG$144/nighttotal: SG$4032 (28 )
Historic Old Towne
Garden Of Lotus
2 2
apartment , Portsmouth
This charming 2-bedroom apartment is located in Old Towne Portsmouth, just a short walk from the city centre and its many restaurants, shops and attractions. The property has received excellent ratings for location, cleanliness and overall user experience. The apartment is ideal for families or groups of up to 6 guests and features a fully equipped kitchen, a private garden and parking. It also benefits from air conditioning, a dishwasher, a microwave and a private entrance, plus the added bonus of a parking pass.
9.8 355 reviews
Chesapeake, VA
17/07 – 20/07
SG$209/nighttotal: SG$627 (3 )
King Guest Suite - A Togar Vacation Rental
1 2
apartment , Chesapeake
This one-bedroom flat is located in Deep Creek South, Chesapeake, just a short drive from the Cahoon Plantation Golf Course and the Great Dismal Swamp National Wildlife Refuge. It has received excellent ratings for location, cleanliness and overall experience. The apartment has a bathroom and can accommodate up to three guests. It offers a range of amenities, including a fully equipped kitchen, a private patio, a washing machine, and a garden, making it ideal for a relaxing stay.
9.0 12 reviews
Chesapeake, VA
08/07 – 13/07
SG$555/nighttotal: SG$2775 (5 )
Spacious Chesapeake Home W/ Pool Table!
4 5
apartment , Chesapeake
This 4-bedroom Chesapeake holiday home is situated in Western Branch North, just a short distance from Chesapeake Square Mall and a drive from Portsmouth City Park and the Chesapeake Arboretum. It has received very good ratings from previous guests. The property offers 223 square metres of space, accommodating up to 8 guests, with 4 bedrooms and 3 bathrooms. It features a range of amenities, including a private yard, a deck, a pool table, a jetted tub, smart TVs, a fireplace, a washer and dryer, and free Wi-Fi.
8.0 7 reviews
Chesapeake, VA
17/07 – 20/07
SG$427/nighttotal: SG$1281 (3 )
Crown Jewel In The Neighborhood.
3 2
apartment , Portsmouth
This Portsmouth holiday home is situated approximately 2.7km from Rivers Casino Portsmouth and 3.5km from Portsmouth City Park, with the Commodore Theatre and Children's Museum of Virginia within a 9.7km radius. The three-bedroom, three-bathroom property sleeps six guests and includes amenities such as a washing machine, iron and ironing board, and air conditioning; its proximity to major roads offers easy access to other regional attractions.
10 4 reviews
Chesapeake, VA
01/07 – 31/07
SG$169/nighttotal: SG$5070 (30 )
Country House Is Perfect For Remote Work Location
2 2
apartment , Virginia Beach
This two-bedroom apartment is located in the Tri-city area of Virginia Beach, Chesapeake, and Norfolk, just 5 kilometres from Sentara Hospital at Princess Anne and the Virginia Beach Municipal Center. The property has received excellent ratings for its location, cleanliness, and overall user experience. The apartment features a spacious backyard and a furnished deck, perfect for relaxing or hosting small gatherings. Guests have access to the entire home, including a small garage, and can enjoy amenities such as air conditioning, a fully equipped kitchen, and dedicated workspaces in each bedroom.
10 35 reviews
Chesapeake, VA
17/07 – 20/07
SG$411/nighttotal: SG$1233 (3 )
Charming Quiet Carriage House
1 2
house , Virginia Beach
The Carriage House is situated in a tranquil wooded area just 8 kilometres from Virginia Beach, close to the Amphitheatre, Performing Arts Centre and a sports complex, with easy access to shops and restaurants. This charming self-catering property has consistently received excellent ratings for its location, cleanliness, and overall experience. The apartment is located above a detached garage and offers a comfortable and private space for up to four guests. The Carriage House is equipped with a fully fitted kitchen, a washing machine and dryer, and a new queen-size bed, plus a pull-out sofa for additional guests.
8.0 1 review
Chesapeake, VA
28/06 – 08/08
SG$226/nighttotal: SG$9266 (41 )
Home Away From Home! Townhome
1 1
apartment , Chesapeake
This Chesapeake townhome is ideally situated in Greenbrier, offering easy walking access to local parks, a lake, shops, restaurants, and theatres. The two-bedroom, two-bathroom property sleeps four guests, features a fully equipped kitchen with dishwasher, in-unit laundry, multiple Roku TVs, and a designated workspace; enjoy nearby outdoor recreation opportunities.
8.3 3 reviews
Chesapeake, VA
17/07 – 20/07
SG$464/nighttotal: SG$1392 (3 )
Pet-friendly Norfolk Retreat ~ 7 Mi To Beach!
3 2
house , Norfolk
This Norfolk holiday home is located just 7 kilometres from the beach, 4.5 kilometres from Topgolf Virginia Beach, and 10 kilometres from Mount Trashmore Park, offering a convenient base for exploring the area. The property is ideal for families or groups of friends, with three bedrooms, two bathrooms, and a spacious 158 square metre floor area, accommodating up to six guests. The house is fully equipped with everything you need for a comfortable stay, including a kitchen with a fridge, microwave oven, and dishwasher, as well as air conditioning, a spa, and parking. Pets are welcome, and free Wi-Fi is available throughout the property.
9.7 72 reviews
Chesapeake, VA
17/07 – 20/07
SG$300/nighttotal: SG$900 (3 )
An Entire House In Va Beach...just For Two!
1 2
apartment , Virginia Beach
This Virginia Beach ranch-style house, offering complete privacy, is conveniently located in an unspecified area of the city; precise proximity to landmarks requires further clarification. The single-bedroom property boasts two bathrooms, a full kitchen with fridge, microwave, and dishwasher, and accommodates up to two guests, with a ground-level deck and off-street parking.
Chesapeake, VA
12/10 – 18/02
SG$129/nighttotal: SG$16641 (129 )
Serene Lodging With Indoor Fireplace
2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 1.8km from Virginia Wesleyan University, within 5km of Sentara Leigh Hospital and Norfolk Premium Outlets. This 71-square-metre property offers two bedrooms, one bathroom, sleeps two guests, and includes a fully equipped kitchen, Jacuzzi, free Wi-Fi, and in-unit laundry facilities.
10 20 reviews
Chesapeake, VA
19/07 – 18/10
SG$177/nighttotal: SG$16107 (91 )
Condo Near Portsmouth Naval On Webster Avenue
1 1
apartment , Portsmouth
This Portsmouth apartment, ideal for families or groups of up to six, is situated less than 1.6km from Portsmouth Naval Hospital and 8km from the Rivers Casino. The three-bedroom, one-bathroom flat offers free internet, air conditioning, parking, and a fully equipped kitchen; enjoy easy access to local attractions and a peaceful atmosphere.
Chesapeake, VA
01/07 – 31/07
SG$212/nighttotal: SG$6360 (30 )
Sojourn At Colley Manor Unit 3 Sleeps 4
2 2
apartment , Norfolk
Colley Manor Unit 3, located in Norfolk, offers convenient access to the Norfolk Botanical Garden (10.6 km) and Topgolf Virginia Beach (14.3 km), placing guests within easy reach of key attractions. This two-bedroom apartment, spanning 81 square metres, comfortably sleeps six guests and includes amenities such as free Wi-Fi, a fully equipped kitchen with dishwasher, and parking, making it ideal for families or groups exploring Norfolk and Virginia Beach.
Best family friendly Chesapeake, VA holiday rentals
Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals
9.9 64 reviews
Chesapeake, VA
25/09 – 30/09
SG$322/nighttotal: SG$1610 (5 )
Peaceful, Private Studio Apartment.
1 2
house , Chesapeake
This detached studio apartment is located in a peaceful neighbourhood in Chesapeake, just 8 kilometres from the city centre. The self-contained studio offers a private outdoor space with a fire pit, parking for two vehicles, and modern amenities including air conditioning, a hybrid mattress, a large shower, and Wi-Fi.
10 196 reviews
Chesapeake, VA
25/09 – 30/09
SG$344/nighttotal: SG$1720 (5 )
Gorgeous Olde Towne Historic Home - Modern Updates
3 4
apartment , Portsmouth
This charming 1880s home is located in Olde Towne Portsmouth, just 1 kilometre from the Elizabeth River harbour, a 3-minute walk from the ferry to Norfolk's downtown and a 5-minute walk to High Street with its shops, restaurants, and cultural attractions. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers. The house has three bedrooms and two bathrooms, accommodating up to seven guests. It offers a range of modern amenities, including a fully equipped kitchen, air conditioning, a private garden, parking, and free internet access, as well as unique historic features like original pinewood floors, windows, doors, and antique doorknobs.
10 26 reviews
Chesapeake, VA
25/09 – 30/09
SG$330/nighttotal: SG$1650 (5 )
Historic Private Guest Apartment
1 2
apartment , Norfolk
This Norfolk apartment, situated in a historic district near the Elizabeth River, offers easy walking access to shops, restaurants, and scenic waterfront views. The self-contained flat comprises two bedrooms, one-and-a-half bathrooms, a full kitchen with dishwasher, and accommodates up to four guests, boasting a private entrance within a historic home and on-site parking.
9.4 18 reviews
Chesapeake, VA
08/07 – 13/07
SG$408/nighttotal: SG$2040 (5 )
Kene's Luxury Retreat Near Va Beach+free Parking.
3 5
apartment , Portsmouth
This family-friendly, three-bedroom, two-storey residence is located in a residential area of Portsmouth, providing convenient access to local attractions such as the Historic Dockyard, approximately 3.5 kilometres away, without being in the immediate city centre. This comfortable abode offers Wi-Fi, air conditioning, and parking, with a kitchen equipped with a freezer and dishwasher, accommodating up to eight guests and featuring a spacious backyard ideal for relaxation.
Best Chesapeake, VA holiday rentals with parking
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
SG$230/nighttotal: SG$29670 (129 )
Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located
4 2
apartment , Norfolk
This four-bedroom house in central Norfolk offers convenient access to downtown attractions and is a short drive from the Virginia Beach oceanfront, with proximity to Town Point Park and the Pagoda and Oriental Garden. This pet-friendly property accommodates up to eight guests and features a fully equipped kitchen with a microwave oven and dishwasher, air conditioning, parking, and two bathrooms, ensuring a comfortable stay with amenities such as an iron and hair dryer.
8.0 1 review
Chesapeake, VA
28/06 – 08/08
SG$136/nighttotal: SG$5576 (41 )
Gorgeous 1 Bedroom With Free Wifi & Street Parking
1 1
apartment , Chesapeake
This smoke-free apartment is located in Western Branch North, just 3.8 kilometres from Chesapeake Square Mall and within a 9.6 kilometre radius of Sentara BelleHarbour and Bon Secours Health Center At Harbour View. The surrounding area is quiet and residential, offering a peaceful retreat after exploring Chesapeake. The apartment has one bedroom and one bathroom, comfortably accommodating up to two guests. It features a private garden, a patio, a jacuzzi, a washing machine, a fully equipped kitchenette, free Wi-Fi, and a Smart TV, ensuring a comfortable and convenient stay.
9.6 110 reviews
Chesapeake, VA
08/07 – 13/07
SG$298/nighttotal: SG$1490 (5 )
Walk To The Casino! Sleeps 8, Close To Everything
1 5
apartment , Portsmouth
This Portsmouth apartment is conveniently located within walking distance of the casino and a short drive (under 10km) to Norfolk, Virginia Beach, and Chesapeake. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers. The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It comes with a fully equipped kitchen, laundry facilities, a private backyard, and smart home features, ensuring a comfortable and enjoyable stay.
9.9 129 reviews
Chesapeake, VA
08/07 – 13/07
SG$1178/nighttotal: SG$5890 (5 )
The Point! Private Waterfront Oasis!
1 5
apartment , Norfolk
This Norfolk holiday home, ideally situated near Virginia Beach, offers easy access to Oceanview Beach and attractions such as Rivers Casino and the Waterside District, with distances to these locations needing clarification. Sleeping up to 10 guests in four bedrooms and two bathrooms, this self-catering property boasts a fully equipped kitchen, air conditioning, a garden, fitness centre, parking, and excellent guest reviews, promising a comfortable stay.
Frequently asked questions about holiday rentals in Chesapeake, VA
What are the top family-friendly attractions in Chesapeake, VA?
The Chesapeake Arboretum is a great choice for families with its nature trails and gardens. The Children's Museum of Virginia is a fun place for kids of all ages, and the Chesapeake Bay Foundation's Brock Environmental Center offers educational and interactive exhibits about the bay.
What are the best Airbnb and vacation rentals in Chesapeake, VA?
When is the best time to book a vacation rental in Chesapeake, VA?
The best time to book a vacation rental in Chesapeake is during the spring or autumn. The weather is mild and pleasant, and the crowds are smaller. You'll find good deals on rentals during these seasons.
What are the most popular Airbnbs in Chesapeake, VA?
What events or festivals should visitors check out in and around Chesapeake, VA?
The Chesapeake Bay Wine Festival is a popular event in the area, held every year in the spring. The Chesapeake Arts Festival is another great choice, featuring live music, art exhibits, and food vendors. The Virginia Beach Boardwalk is a short drive from Chesapeake and hosts many events throughout the year.
What are the best vacation rentals with a pool in Chesapeake, VA?
What are the best budget-friendly activities in Chesapeake, VA?
The Chesapeake Arboretum is a great option for a free day out, with its nature trails and gardens. The Chesapeake Bay Foundation's Brock Environmental Center also offers free admission. You can also enjoy a scenic walk or bike ride along the Chesapeake Bay.
What are the best rentals for families and kids in Chesapeake, VA?
What are the best restaurants with local dishes in Chesapeake, VA?
For local seafood, try The Fish House Restaurant in the Great Bridge area. They have a great view of the water and serve fresh, delicious dishes. For a more casual option, try The Chesapeake Inn, known for its crab cakes and other local favourites.
What are the best rentals or Airbnbs with a jacuzzi in Chesapeake, VA?
What are the best walking or cycling routes in Chesapeake, VA?
The Chesapeake Bay Trail is a popular choice for walking or cycling, offering scenic views of the bay. The Dismal Swamp Canal Trail is another great option, with its historic significance and natural beauty.
Are there pet-friendly attractions in Chesapeake, VA?
The Chesapeake Arboretum is very pet-friendly, allowing dogs on leashes. The Chesapeake Bay Foundation's Brock Environmental Center also welcomes well-behaved dogs on leashes.
What are the benefits of choosing a vacation rental in Chesapeake, VA?
Vacation rentals offer more space and privacy than hotels. They are also often more affordable, especially for families or groups travelling together. Many vacation rentals offer unique features like kitchens, laundry facilities, and outdoor spaces.
Destinations nearby
Best Chesapeake, VA holiday rentals with a balcony
10 1 review
Chesapeake, VA
01/12 – 29/12
SG$286/nighttotal: SG$8008 (28 )
Cambridge Knights A 3 Bedroom Home Full Of Charm
3 2
apartment , Portsmouth
This Portsmouth holiday home is located just 3km from attractions like the Emanuel AME Church, Commodore Theatre, and the Virginia Sports Hall of Fame and Museum, making it a great base for exploring the city. The surrounding area is quiet and residential, offering a peaceful escape from the hustle and bustle of the city centre. The property has three bedrooms and two bathrooms, comfortably accommodating up to six guests. It features a fully equipped kitchen, a terrace or balcony, a spa, and free parking, as well as modern amenities like Wi-Fi and air conditioning.
10 1 review
Chesapeake, VA
12/10 – 18/02
SG$231/nighttotal: SG$29799 (129 )
Cheerful 2 Bedroom Home Near Virginia Wesleyan
2 2
apartment , Virginia Beach
This Northwest Virginia Beach holiday home is situated 0.5km from Virginia Wesleyan University, within 5km of Cypress Point Country Club, and less than 5km from Norfolk Premium Outlets. This 89 square metre property offers two bedrooms, one bathroom, sleeps four guests, and includes a fully equipped kitchen with oven and microwave, a private balcony, on-site barbecue grills, and in-unit laundry facilities.
9.6 37 reviews
Chesapeake, VA
25/09 – 30/09
SG$239/nighttotal: SG$1195 (5 )
Historic Old Towne Southern Charm
2 2
apartment , Portsmouth
This charming 2-bedroom flat is located in Old Towne Portsmouth, just a short walk from the city's restaurants, shops, and attractions. The area is known for its historic architecture and lively atmosphere, making it a great base for exploring the city. The apartment has a very good user rating, indicating a positive experience for previous guests. This spacious home can comfortably accommodate up to 7 guests. It features a well-equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a terrace, and a garden. Guests can also enjoy free Wi-Fi and the convenience of a washing machine and dryer.
10 7 reviews
Chesapeake, VA
27/06 – 04/07
SG$613/nighttotal: SG$4291 (7 )
Norfolk 3br Cozy Stay. Central To All & Comfort. Families & Contractors!
3 3
apartment , Norfolk
This charming apartment is located in Norfolk, just 2 kilometres from the Virginia Zoo and 5 kilometres from the Norfolk Scope. It has been rated excellent by previous guests. The apartment has 3 bedrooms and 2 bathrooms, providing comfortable accommodation for up to 6 guests. It comes equipped with a kitchen, air conditioning, a Jacuzzi, a terrace, parking, and Wi-Fi, allowing you to relax and enjoy your stay.
Best Chesapeake, VA holiday rentals with air conditioning
9.1 59 reviews
Chesapeake, VA
01/12 – 29/12
SG$110/nighttotal: SG$3080 (28 )
Spiral Loft
1 2
apartment , Norfolk
This Norfolk apartment is situated in the Ghent Historic District, a short walk from Norfolk's commercial centre, offering easy access to the waterfront and historical sites along former trolley routes. The self-catering flat, sleeping two guests, includes a dishwasher, air conditioning, parking, and benefits from excellent guest reviews for cleanliness and location.
9.6 4 reviews
Chesapeake, VA
12/10 – 18/02
SG$187/nighttotal: SG$24123 (129 )
Sojourn's Spacious Apartment In Colley Manor
2 2
apartment , Norfolk
This Ghent flat in Norfolk is situated near Colley Avenue's restaurants and cafes, major hospitals (CHKD, EVMS, and Norfolk General), and offers easy access to public transport, including the Tide light rail to Norfolk city centre. The 84-square-metre (904-square-foot) two-bedroom, one-bathroom property sleeps four, includes a kitchen with a fridge, microwave, and dishwasher, and provides parking, air conditioning, internet access, and a contactless self check-in; a travel cot and high chair are available for an extra charge.
8.5 21 reviews
Chesapeake, VA
27/06 – 04/07
SG$238/nighttotal: SG$1666 (7 )
Creek-side Captain's Retreat
1 3
apartment , Portsmouth
The Captain's Retreat is a three-bedroom house situated in a central Portsmouth location, offering easy access to the city's attractions. This creek-side property sleeps six, boasts a fully equipped kitchen with fridge, freezer, and dishwasher, plus air conditioning, a garden, parking, and excellent guest reviews; pets are welcome.
Chesapeake, VA
27/06 – 04/07
SG$269/nighttotal: SG$1883 (7 )
Condo ∙ 1 Bedroom ∙ 6 Guests
1 2
apartment , Chesapeake
This apartment is conveniently located near the Virginia Beach business district and General Dynamics in Chesapeake, a 40-kilometre drive from the Virginia Beach oceanfront. The surrounding area offers easy access to both business and leisure activities, making it a popular choice for travellers. This one-bedroom apartment can accommodate up to six guests comfortably, with two queen beds and a sofa bed. Guests can enjoy a range of amenities, including a fully equipped kitchen, a swimming pool, a hot tub, a fitness centre, and free parking.