Holiday Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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Best Holiday rentals and Airbnb offers in Chesapeake, VA

Best family friendly Chesapeake, VA holiday rentals

Among the 677 accommodations in Chesapeake, VA, here are the 4 best family friendly rentals

Peaceful, Private Studio Apartment. - Chesapeake, VA
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.
Gorgeous Olde Towne Historic Home - Modern Updates - Chesapeake, VA
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.
Historic Private Guest Apartment - Chesapeake, VA
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.
Kene's Luxury Retreat Near Va Beach+free Parking. - Chesapeake, VA
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

Cozy 4 Bed 2 Bath Home - Norfolk, Centrally Located - Chesapeake, VA
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.
Gorgeous 1 Bedroom With Free Wifi & Street Parking - Chesapeake, VA
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.
Walk To The Casino! Sleeps 8, Close To Everything - Chesapeake, VA
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.
The Point! Private Waterfront  Oasis! - Chesapeake, VA
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?

    King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Econo Lodge Chesapeake Route 13 And I-464 are the most popular Airbnb and vacation rentals in Chesapeake, VA among travelers.

  • 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?

    Modern Condo In Western Branch, Comfortable Home | Long Stay Discount Available and The Peaceful Oasis 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?

    The best rentals for families and kids in Chesapeake, VA are King Guest Suite - A Togar Vacation Rental, Townhome In Convient Location and Modern Luxury Peace & Quiet.

  • 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?

    The best vacation rentals or Airbnb with a jacuzzi in Chesapeake, VA are Rock Star Mansion, Peace On The Lake and Gorgeous 1 Bedroom With Free Wifi & Street Parking.

  • 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

Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
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.
Cheerful 2 Bedroom Home Near Virginia Wesleyan - Chesapeake, VA
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.
Historic Old Towne Southern Charm - Chesapeake, VA
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.
Norfolk 3br Cozy Stay. Central To All & Comfort. Families & Contractors! - Chesapeake, VA
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

Spiral Loft - Chesapeake, VA
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.
Sojourn's Spacious Apartment In Colley Manor - Chesapeake, VA
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.
Creek-side Captain's Retreat - Chesapeake, VA
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.
Condo ∙ 1 Bedroom ∙ 6 Guests - Chesapeake, VA
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.
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