Vacation Rentals in Chesapeake, VA

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Chesapeake, VA holiday rentals
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939 Holiday rentals and Airbnb in Chesapeake, VA

Outstanding Family Holiday Rentals in Chesapeake, VA

Compare family holiday rentals in Chesapeake, VA with space and amenities for all.

Waterfront Oasis: Fishing Pier, Pool, Beach Access - Chesapeake, VA
10 10 reviews

Waterfront Oasis: Fishing Pier, Pool, Beach Access

house, Chesapeake
This Chesapeake flat is located in the Deep Creek district, directly on the Elizabeth River, offering waterfront living with private marina club access, a fishing pier, docks, and beach access.
This 3-bedroom, 2-bathroom residence accommodates up to 8 guests and features air conditioning, internet, a kitchen, swimming pool, fitness centre, parking, and a dedicated dog park.
Modern, Homely 3-bdrm|wparking|centrally  Located. - Chesapeake, VA
9.4 246 reviews

Modern, Homely 3-bdrm|wparking|centrally Located.

apartment, Portsmouth
This apartment is situated in Portsmouth, within walking distance of shops, restaurants and amenities, and just a few kilometres from the historic downtown area and the Norfolk Zoo. The apartment has received excellent ratings for cleanliness and user experience, with a very good location rating.
The apartment offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It comes equipped with a kitchen including a fridge, freezer, microwave and dishwasher, as well as air conditioning, a garden and parking.
Cozy Quarters Near Nmcp - Chesapeake, VA
10 4 reviews

Cozy Quarters Near Nmcp

apartment, Portsmouth
This two-bedroom duplex flat is situated in Portsmouth, a short distance from the Naval Medical Center and surrounding shipyards, making it an ideal base for professionals working in the area.
This family-friendly accommodation offers a garden, air conditioning, and a kitchen equipped with a fridge and microwave, providing comfort for up to four guests with one bathroom.
Luxury Lakefront Estate & Guest House W/ Pool - Chesapeake, VA
10 12 reviews

Luxury Lakefront Estate & Guest House W/ Pool

apartment, Portsmouth
This luxurious lakefront estate sits on Crystal Lake, offering a tranquil retreat just 10km outside of Portsmouth, providing easy access to the city's attractions. The property has received excellent ratings for its cleanliness, location, and overall experience, making it a top choice for discerning travellers.
The estate features a grand main house and a separate guest house, accommodating up to 16 guests. Guests can enjoy a refreshing dip in the pool, relax in the Jacuzzi, or prepare meals in the gourmet kitchen, all while taking in stunning lake views.

Best Chesapeake, VA holiday rentals with parking

Fully Renovated And Modernized Home In Chesapeake - Chesapeake, VA
10 22 reviews

Fully Renovated And Modernized Home In Chesapeake

apartment, Chesapeake
This Chesapeake apartment is conveniently located just 2 kilometres from Portlock Galleries at SoNo and an 8-minute drive from Greenbrier Mall. It has received excellent guest reviews, making it a popular choice for travellers. The apartment has 3 bedrooms and 3 bathrooms, comfortably accommodating up to 8 guests. The property comes with a range of features, including a Smart TV, Wi-Fi, parking, and a barbecue area, providing everything you need for a comfortable stay.
Your Home Away From Home And Near Va Beach - Chesapeake, VA
8.8 12 reviews

Your Home Away From Home And Near Va Beach

apartment, Portsmouth
This four-bedroom Portsmouth house, sleeping up to ten guests, is situated in a quiet neighbourhood, approximately 24km from Portsmouth Naval Hospital and 40km from Virginia Beach.
The property boasts a spacious interior with a large living room, dining room, office, fully equipped kitchen including dishwasher, two bathrooms (one with Jacuzzi), Wi-Fi, Roku TVs, and private gardens with parking; ideal for families or groups visiting the area's military bases.
Condo Near Portsmouth Naval On Webster Avenue - Chesapeake, VA
10 25 reviews

Condo Near Portsmouth Naval On Webster Avenue

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.
Perfect Getaway In Chesapeake - Chesapeake, VA
No reviews

Perfect Getaway In Chesapeake

apartment, Chesapeake
This Chesapeake apartment is centrally located, offering easy access to local shops and restaurants, and a 32km drive to the Virginia Beach Boardwalk.
The three-bedroom, three-bathroom property sleeps up to 10 guests and includes a private swimming pool, parking, and Wi-Fi; two sitting areas and a patio add to its appeal.

Frequently asked questions about holiday 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 shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are often lower. The summer months, June to August, are popular with tourists, so expect higher prices and larger crowds.
  • What are the best Airbnb and holiday rentals in Chesapeake, VA?

  • What are the best budget-friendly activities in Chesapeake, VA?

    Chesapeake offers many budget-friendly activities, including a visit to the Chesapeake Arboretum, exploring the Chesapeake Bay waterfront, or taking a walk or bike ride on the Chesapeake Bay Trail. You can also enjoy a picnic lunch at the Chesapeake City Park or spend an afternoon browsing the shops and restaurants in the Greenbrier area.
  • What are the most popular Airbnbs in Chesapeake, VA?

  • What are the best restaurants with local dishes in Chesapeake, VA?

    For a taste of local seafood, try the Chesapeake Bay Bridge-Tunnel Seafood Restaurant. If you prefer something a bit more casual, try the Chesapeake Bay Brewing Company, which offers a range of craft beers and pub grub. For a more upscale dining experience, try the Chesapeake Inn, which offers a fine-dining menu with a focus on fresh, local ingredients.
  • What are the best holiday rentals with a pool in Chesapeake, VA?

    Modern Condo In Western Branch, The Peaceful Oasis and Cheshire Retreat are the best holiday rentals with a pool in Chesapeake, VA.

  • What are the best walking or cycling routes in Chesapeake, VA?

    The Chesapeake Bay Trail is a popular choice for walking and cycling, offering scenic views of the Chesapeake Bay. The trail is over 160km long and runs through various parts of the city, including the Chesapeake Arboretum and the Chesapeake City Park. For a shorter walk, you can explore the trails at the Chesapeake Arboretum or the Chesapeake Botanical Gardens.
  • 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.

  • Are there pet-friendly attractions in Chesapeake, VA?

    Yes, Chesapeake is a pet-friendly city. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake City Park has a dedicated dog park. Many restaurants also have outdoor seating where you can bring your furry friend.
  • What are the best rentals or Airbnbs with a jacuzzi in Chesapeake, VA?

    The best holiday 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 benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer a more spacious and comfortable alternative to hotels. They are often located in residential areas, which can provide a more authentic experience of the city. They also offer more privacy and flexibility than traditional accommodations, allowing you to prepare your own meals and set your own schedule.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    Chesapeake is home to the Chesapeake Regional Healthcare YMCA, which offers a range of fitness and sports facilities, including a swimming pool, a gymnasium, and a fitness centre. For outdoor activities, the Chesapeake City Park offers a variety of sports facilities, including baseball fields, tennis courts, and a skate park.

Popular destinations

Top-Rated Holiday Rentals with a Balcony in Chesapeake, VA

Relax outdoors and watch the town come alive from the elevated vantage of holiday rentals with a balcony in Chesapeake, VA.

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental - Chesapeake, VA
9.0 53 reviews

Historic Olde Towne 2 Bedroom 1 Bath 1100sq Ft Vacation Rental

apartment, Portsmouth
This Portsmouth apartment, a short walk from the Commodore Theatre and the Virginia Sports Hall of Fame, enjoys a riverfront location offering scenic views and is within 2.4km of the Children's Museum of Virginia and the Portsmouth Naval Shipyard Museum.
The two-bedroom, one-bathroom flat sleeps four, features free WiFi, a DVD player, a fully equipped kitchen, on-site parking, and a terrace; board games and books are also provided for guests' entertainment.
Bright Chesapeake Home Near Shopping & Dining - Chesapeake, VA
No reviews

Bright Chesapeake Home Near Shopping & Dining

house, Chesapeake
Holiday house to rent. You will stay in Chesapeake.
Services and facilities include a fridge, free parking and air conditioning.
Beautiful Home In Chesapeake - Chesapeake, VA
10 5 reviews

Beautiful Home In Chesapeake

house, Chesapeake
This Chesapeake property is conveniently located near Mount Trashmore Park (13km), the Norfolk Botanical Garden (20km), and Virginia Beach (a short drive away), offering easy access to local attractions and Norfolk International Airport (18km).
The 136 square metre house boasts three bedrooms, two bathrooms, sleeps twelve guests, and includes a fully equipped kitchen, free Wi-Fi, private parking, and air conditioning.
Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8

apartment, Portsmouth
This holiday home is located in Portsmouth, just 1.5 km from Rivers Casino Portsmouth, and within 10 km of Portsmouth City Park and Frank D Lawrence Stadium. It has consistently received excellent user ratings, making it a popular choice for travellers.
The property offers 93 square metres of space and can comfortably accommodate up to 6 guests in its 3 bedrooms. The kitchen comes equipped with a fridge, microwave, oven, and dishwasher, while the garden provides a relaxing outdoor space. Guests can also enjoy free Wi-Fi, air conditioning, a terrace, and parking.

Best Chesapeake, VA holiday rentals with air conditioning

The Mermaids Lair ‍️ - Chesapeake, VA
9.0 15 reviews

The Mermaids Lair ‍️

apartment, Portsmouth
This Portsmouth waterfront apartment offers stunning Crystal Lake views and private dock access, situated approximately 16km from Norfolk's attractions, 32km from Norfolk Naval Base, and 40km from Virginia Beach.
The self-catering studio, sleeping two guests, features a kitchenette with microwave and fridge, a custom shower, a shared fire pit, and automatic gate access for enhanced security.
Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse - Chesapeake, VA
9.9 66 reviews

Stylish Two Bdrm, 1 1/2 Bth, King Bed Townhouse

apartment, Portsmouth
This two-bedroom apartment in Portsmouth is situated less than a mile from the new Rivers Casino, offering easy access to entertainment and dining options. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The property can comfortably accommodate up to four guests and features a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher. The apartment also benefits from air conditioning, a garden, and parking, ensuring a comfortable and convenient stay.
Central Chesapeake Stay Near Mall, Trails & Parks - Chesapeake, VA
No reviews

Central Chesapeake Stay Near Mall, Trails & Parks

apartment, Chesapeake
This three-bedroom flat in Chesapeake is situated in the Greenbrier district, offering convenient access to Greenbrier Mall, Waterside District, and the Veterans United Home Loans Amphitheater at Virginia Beach, with major highways readily available for exploring the wider Hampton Roads area.
This accommodation accommodates up to eight guests and provides air conditioning and internet, making it a comfortable base for exploring local attractions such as Jillian's Billiards and the Chesapeake Arboretum.
The Western Branch Professionals Townhome - Chesapeake, VA
9.6 27 reviews

The Western Branch Professionals Townhome

house, Chesapeake
This Chesapeake townhome, situated in a quiet residential neighbourhood, is conveniently located within 16km of Chesapeake Square Mall, 32km from Downtown Norfolk, and under 80km from Busch Gardens Williamsburg.
The three-bedroom, two-and-a-half-bathroom property sleeps six guests and features a fully equipped kitchen with stainless steel appliances, a private first-floor master bedroom with en-suite, a washer/dryer, and outdoor seating; nearby attractions include Virginia Beach's oceanfront and Ocean Breeze Park, both within a 56-72km radius.

Top Rated Luxury Holiday Rentals in Chesapeake, VA

Treat yourself to smart-home features, high-end interiors, and curated artwork at luxury holiday rentals in Chesapeake, VA.

5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room - Chesapeake, VA
9.5 180 reviews

5 Minutes To The Casino!family Sized Home 3 Bedroom With Patio And A Game Room

apartment, Portsmouth

Top-Rated Downtown Holiday Rentals in Chesapeake, VA

Find centrally located holiday rentals in Chesapeake, VA close to attractions and transport.

Simply Amazing In Chesapeake - Chesapeake, VA
10 40 reviews

Simply Amazing In Chesapeake

apartment, Chesapeake
Tush And Mane - Chesapeake, VA
9.3 9 reviews

Tush And Mane

house, Chesapeake
The Refresh Experience - Chesapeake, VA
9.2 74 reviews

The Refresh Experience

house, Chesapeake
Entire Apartment In Chesapeake, Virginia - Chesapeake, VA
9.8 11 reviews

Entire Apartment In Chesapeake, Virginia

apartment, Chesapeake