Compare Vacation Rentals & Airbnb in Chesapeake, VA

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Chesapeake, VA vacation rentals
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677 Rentals and Airbnb in Chesapeake, VA

Sojourn At Colley Manor Unit 4 Sleeps 4 - Chesapeake, VA
Chesapeake, VA
01/07 – 31/07
$231/nighttotal: $6930 (30 )

Sojourn At Colley Manor Unit 4 Sleeps 4

2 2
apartment, Norfolk
Colley Manor Unit 4, situated in Norfolk, is conveniently located 10.6 km from the Norfolk Botanical Garden and 14.3 km from Topgolf Virginia Beach, offering easy access to Virginia Beach attractions.
This two-bedroom apartment, sleeping four, boasts a 93 square metre floor area, a fully equipped kitchen including a dishwasher, free Wi-Fi, and parking, making it ideal for families or small groups visiting Norfolk.
The Hideaway, A Super Cozy Cottage In Portsmouth - Chesapeake, VA
9.3 15 reviews
Chesapeake, VA
29/06 – 03/08
$114/nighttotal: $3990 (35 )

The Hideaway, A Super Cozy Cottage In Portsmouth

2 2
apartment, Portsmouth
This two-bedroom apartment is located in Portsmouth, just 2.4 kilometres from the historic Old Town and its waterfront, offering easy access to the city's attractions.
The apartment, which can accommodate up to three guests, features a fully equipped kitchen, air conditioning, parking, and internet access, making it ideal for a comfortable and convenient stay in Portsmouth.
Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!! - Chesapeake, VA
9.2 28 reviews
Chesapeake, VA
27/06 – 30/06
$380/nighttotal: $1140 (3 )

Charming 2 Bedroom, 2 Bath Townhome Located In Portsmouth, Simple And Elegant!!

2 3
apartment, Portsmouth
This Portsmouth townhouse, centrally located in Hampton Roads, offers easy access to the Rivers Casino (distance unspecified) and Virginia Beach Boardwalk (driving distance unspecified).
The 84-square-metre (904 sq ft) property sleeps four guests in two bedrooms with queen-size beds and smart TVs, and includes a fully equipped kitchen, private garden, parking, and excellent Wi-Fi.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers! - Chesapeake, VA
Chesapeake, VA
14/08 – 16/08
$664/nighttotal: $1328 (2 )

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great For Business Travelers!

1 2
apartment, Chesapeake
This Chesapeake, Virginia aparthotel offers a convenient location, a 9-minute walk from the Chesapeake Conference Centre and a 1.8km drive from Greenbrier Mall, with easy beach access.
The self-catering apartment features a fully equipped kitchen, one bedroom, one bathroom, sleeps two guests, and includes a swimming pool, jacuzzi, and on-site parking.
Beachy And Chic 3 Bedroom Townhome Near Towncenter - Chesapeake, VA
10 3 reviews
Chesapeake, VA
29/06 – 03/08
$359/nighttotal: $12565 (35 )

Beachy And Chic 3 Bedroom Townhome Near Towncenter

1 2
apartment, Virginia Beach
This three-bedroom, two-bathroom townhouse is situated near Virginia Beach's Towne Centre, offering convenient access to Interstate 264, local military bases, and the Chesapeake Bay.
The property, sleeping up to seven guests, boasts a fully equipped kitchen, a downstairs workspace, and a large fenced backyard; nearby attractions include the Chesapeake Bay for water activities.
The Cozy Dominion Suite In Chesapeake - Chesapeake, VA
8.5 78 reviews
Chesapeake, VA
30/06 – 02/07
$144/nighttotal: $288 (2 )

The Cozy Dominion Suite In Chesapeake

1 2
apartment, Chesapeake
This Chesapeake condo, situated near shops and restaurants with Downtown Norfolk a 16km drive away, offers convenient access to local amenities and city attractions.
The one-bedroom, one-bathroom apartment sleeps three, featuring a queen-size bed, fully equipped kitchen with dishwasher, smart TV, super-fast WiFi, and a Ring Doorbell for added security; parking is also provided.
Newly Remodeled 2 Bedroom Duplex - Chesapeake, VA
10 3 reviews
Chesapeake, VA
31/07 – 31/08
$187/nighttotal: $5797 (31 )

Newly Remodeled 2 Bedroom Duplex

1 2
apartment, Chesapeake
This newly remodelled two-bedroom duplex apartment is situated in a peaceful Chesapeake neighbourhood, with the exact location and distances to landmarks unspecified.
The property, offering a king-size bed in the master and twin beds in the second bedroom, sleeps three guests and includes a fully equipped kitchen, in-unit laundry, Smart TVs, free Wi-Fi, and ample parking; this special offer includes a significant monthly discount.
Downtown Corner Of W. Bute & Dunmore Streets - Chesapeake, VA
9.4 145 reviews
Chesapeake, VA
01/07 – 31/07
$185/nighttotal: $5550 (30 )

Downtown Corner Of W. Bute & Dunmore Streets

1 2
apartment, Norfolk
This one-bedroom flat is situated in a historic neighbourhood in Norfolk, just a few hundred metres from cobblestone streets, gourmet restaurants and the YMCA, and within easy walking distance of the Chrysler Museum of Art. It has received excellent ratings for its location, cleanliness and overall user experience.
The flat can accommodate up to four guests and offers a range of amenities including a well-equipped kitchen, air conditioning, parking, and internet access. Guests can enjoy the outdoor space with benches on three sides of the building, perfect for relaxing or people-watching, and the flat also welcomes small, well-behaved pets.
Norfolk 3br Cozy Stay. Central To All & Comfort. Families & Contractors! - Chesapeake, VA
10 7 reviews
Chesapeake, VA
27/06 – 04/07
$667/nighttotal: $4669 (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.
Cozy Sailboat Stay In Olde Towne Portsmouth - Chesapeake, VA
Chesapeake, VA
17/07 – 20/07
$319/nighttotal: $957 (3 )

Cozy Sailboat Stay In Olde Towne Portsmouth

1 2
boat, Portsmouth
This classic Pearson sailboat offers a unique waterfront camping experience docked in historic Olde Towne Portsmouth, just steps from shops, restaurants, museums, and nightlife, with the Elizabeth River Ferry to Norfolk only a few minutes away. This accommodation for up to three guests includes onboard amenities such as a small fridge, a Keurig coffee maker, and access to two paddle boards for exploring the marina and river, with nearby bathhouses and showers available.
Cute 4 Bed / 2.5 Bath Home W/ Pool - Sleeps 12! 30 Night Min - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$235/nighttotal: $30315 (129 )

Cute 4 Bed / 2.5 Bath Home W/ Pool - Sleeps 12! 30 Night Min

4 2
apartment, Virginia Beach
This four-bedroom home is located in a peaceful neighbourhood just 2 kilometres from Town Centre and the Virginia Beach Oceanfront, and a short distance from Mount Trashmore Park. The property is ideal for families or groups of friends, comfortably sleeping 12 guests across its six beds.
The apartment offers a range of amenities, including a fully equipped kitchen, air conditioning, a private swimming pool, a Jacuzzi, and parking for four cars. Guests can also enjoy the spacious backyard with a barbecue area, perfect for relaxing evenings.
Serene Lodging With Indoor Fireplace - Chesapeake, VA
Chesapeake, VA
12/10 – 18/02
$140/nighttotal: $18060 (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.

Best family friendly Chesapeake, VA vacation rentals

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

Walkable To The Casino And Family Friendly! 3 Bd/2 Ba, Full House, Sleeps 8 - Chesapeake, VA
9.2 7 reviews
Chesapeake, VA
25/09 – 30/09
$461/nighttotal: $2305 (5 )

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

4 2
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.
Spacious Home In Chesapeake - Chesapeake, VA
8.6 4 reviews
Chesapeake, VA
25/09 – 30/09
$622/nighttotal: $3110 (5 )

Spacious Home In Chesapeake

4 4
apartment, Chesapeake
This spacious four-bedroom flat in the Greenbrier district of Chesapeake is located approximately 40 kilometres from Virginia Beach, offering convenient access to Greenbrier Mall and Waterside District for shopping, as well as the Veterans United Home Loans Amphitheater for entertainment.
This family-friendly residence spans 186 square metres and accommodates up to eight guests, featuring a dedicated home theatre with a popcorn maker, a master suite with double vanities and a soaking tub, air conditioning, a garden, and parking.
The Bird’s Nest - Chesapeake, VA
9.8 59 reviews
Chesapeake, VA
08/07 – 13/07
$604/nighttotal: $3020 (5 )

The Bird’s Nest

4 5
apartment, Chesapeake
This apartment is located in the Great Bridge area of Chesapeake, just 32 kilometres from the oceanfront, 8 kilometres from the interstate, and 10 kilometres from Greenbriar Mall, offering a peaceful retreat with a country feel despite its proximity to urban amenities. The property has received excellent ratings for location, cleanliness, and user experience.
The self-catering property can accommodate up to 8 guests and boasts a spacious outdoor area with a large fenced yard and an open field. It also features a tree house, a gazebo with an extension cord for lighting, and a variety of amenities including a Jacuzzi, a garden, and parking.
The Chesapeake Guesthouse - Chesapeake, VA
9.7 61 reviews
Chesapeake, VA
25/09 – 30/09
$348/nighttotal: $1740 (5 )

The Chesapeake Guesthouse

1 2
apartment, Chesapeake
This apartment is situated in the Greenbrier area of Chesapeake, just a short distance from major highways, hospitals, shopping centres, restaurants, entertainment venues, and military bases. It has consistently received excellent ratings for its cleanliness, location, and overall user experience.
The property offers three bedrooms and two and a half bathrooms, comfortably accommodating up to five guests. The apartment features a fully equipped kitchen, a spacious living area, a versatile "Green Room", a large backyard, off-street parking for four vehicles, and a keyless entry system.

Best Chesapeake, VA vacation rentals with parking

Spacious 3 Bedroom Virginia Beach Getaway  30 + Night Stays - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
$386/nighttotal: $13510 (35 )

Spacious 3 Bedroom Virginia Beach Getaway 30 + Night Stays

3 2
apartment, Virginia Beach
This three-bedroom Virginia Beach apartment is situated in Northwest Virginia Beach, approximately 1.6km from Apex Entertainment, 3.2km from Cinema Cafe, and 4km from Mount Trashmore Park.
The 3-bedroom, 2-bathroom property sleeps six guests, boasting a fully equipped kitchen, high-speed Wi-Fi, Smart TV, in-unit laundry, and a fenced backyard; exterior security cameras and a decibel monitor ensure peace of mind.
Monthly, Dog-friendly Home At Orange Blossom - Chesapeake, VA
Chesapeake, VA
31/07 – 31/08
$336/nighttotal: $10416 (31 )

Monthly, Dog-friendly Home At Orange Blossom

3 2
apartment, Virginia Beach
This three-bedroom, four-bathroom apartment is situated in Virginia Beach's Green Run neighbourhood, approximately 24 kilometres from various beaches and close to Norfolk.
The self-catering property offers a spacious open-plan layout, sleeping up to five guests, and boasts a fully fenced backyard, on-site parking, and a fully equipped kitchen including a dishwasher; nearby attractions include Lynnhaven Mall, Landstown Commons, Town Centre, and Mount Trashmore Park.
Waterfront Portsmouth Home  Dock Access - Chesapeake, VA
9.6 4 reviews
Chesapeake, VA
31/07 – 31/08
$565/nighttotal: $17515 (31 )

Waterfront Portsmouth Home Dock Access

3 2
apartment, Portsmouth
This waterfront property is located in Portsmouth, just a short distance from the Waterside Festival Marketplace and Greenbrier Mall, offering easy access to shopping and entertainment. The apartment is also close to the Norfolk Scope and Ted Constant Convocation Center, ideal for those looking to attend events or games.
This spacious apartment can comfortably accommodate up to six guests and features three bedrooms and two bathrooms. Guests can enjoy the stunning views of Hull Creek/Elizabeth River from the terrace or balcony, and relax in the garden or on the dock. The apartment also offers a range of amenities, including a fully equipped kitchen, air conditioning, parking, and internet access.
Sojourn At Colley Manor Unit 4 - Chesapeake, VA
10 1 review
Chesapeake, VA
31/07 – 31/08
$203/nighttotal: $6293 (31 )

Sojourn At Colley Manor Unit 4

2 2
apartment, Norfolk
This Ghent flat in Norfolk is centrally located near Colley Avenue's restaurants and cafes, within easy reach of major hospitals (CHKD, EVMS, Norfolk General) and a short drive (approximately 20 km) from Virginia Beach and Ocean View.
The 93 square metre self-catering property sleeps four, offering two bedrooms, one bathroom, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, parking, and internet access; a travel cot and highchair are available for an extra charge.

Frequently Asked Questions about 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 shoulder seasons, from April to May and September to October. You'll avoid the crowds and enjoy pleasant weather, with temperatures ranging from 15 to 25 degrees Celsius.
  • 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.

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

    Take a walk or bike ride along the Chesapeake Bay Trail, a scenic trail that stretches for over 160 km. You can also visit the Chesapeake Arboretum, a beautiful green space with free admission. And if you're looking for a fun and affordable way to spend an evening, check out the Chesapeake Farmers Market, held every Saturday from May to October.
  • What are the most popular Airbnbs in Chesapeake, VA?

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

    For a taste of Chesapeake's local seafood, try The Crab Pot, a popular spot known for its fresh blue crabs and other seafood dishes. Another great option is The Chesapeake Inn, a waterfront restaurant serving classic Chesapeake Bay dishes like crab cakes and oyster stew.
  • What are the best vacation rentals with a pool in Chesapeake, VA?

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

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

    The Chesapeake Bay Trail is a great option for walking or cycling. It stretches for over 160 km, offering scenic views of the Chesapeake Bay and its tributaries. You can also explore the Chesapeake Arboretum, which has a network of walking trails and a beautiful garden.
  • 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, there are plenty of pet-friendly attractions in Chesapeake. The Chesapeake Arboretum welcomes dogs on leash, and the Chesapeake Bay Foundation's Brock Environmental Center has a dog-friendly outdoor area. Many restaurants also have outdoor seating areas that are pet-friendly.
  • 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 benefits of choosing a vacation rental in Chesapeake, VA?

    Vacation rentals offer more space and privacy than hotels, and they often come with amenities like kitchens and laundry facilities. They can also be more affordable, especially for families or groups. Plus, you'll have the chance to experience life like a local, with access to neighbourhood amenities and a more authentic experience.
  • What are the top sports attractions and facilities in Chesapeake, VA?

    The Chesapeake Sportsplex is a popular destination for sports enthusiasts, with a variety of fields and courts for baseball, softball, soccer, and more. The Chesapeake YMCA also offers a range of sports activities and facilities, including a swimming pool, gym, and fitness classes.

Destinations nearby

Best Chesapeake, VA vacation rentals with a balcony

Luxe Lakefront Portsmouth Home: Fish, Swim & Play! - Chesapeake, VA
10 2 reviews
Chesapeake, VA
01/12 – 29/12
$676/nighttotal: $18928 (28 )

Luxe Lakefront Portsmouth Home: Fish, Swim & Play!

3 2
house, Portsmouth
This lakefront holiday home is located in Portsmouth, just 24km from the Norfolk Botanical Garden and 40km from the King Neptune Statue on the Boardwalk, offering a peaceful retreat close to attractions.
This spacious property has 3 bedrooms, 3 bathrooms, and can comfortably accommodate up to 15 guests. The home is equipped with a range of amenities, including a fully equipped kitchen, air conditioning, a swimming pool, a spa, a garden, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay for all.
Cambridge Knights A 3 Bedroom Home Full Of Charm - Chesapeake, VA
10 1 review
Chesapeake, VA
16/08 – 27/08
$374/nighttotal: $4114 (11 )

Cambridge Knights A 3 Bedroom Home Full Of Charm

3 4
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.
Centrally Located Hampton Roads Home W/ Game Room! - Chesapeake, VA
Chesapeake, VA
25/09 – 30/09
$557/nighttotal: $2785 (5 )

Centrally Located Hampton Roads Home W/ Game Room!

4 2
house, Portsmouth
This centrally located Hampton Roads detached house in Portsmouth offers easy access to attractions, situated 16 kilometres from Norfolk Botanical Garden and 35 kilometres from the King Neptune Statue on the Boardwalk.
This spacious 269 square metre property provides accommodation for up to 15 guests across four bedrooms, featuring a fully equipped kitchen, three bathrooms, air conditioning, a patio, a game room, and complimentary WiFi, with parking and a garden available.
Beach Family Time Enjoy The Backyard Pool And Sunroom - Chesapeake, VA
8.6 36 reviews
Chesapeake, VA
25/09 – 30/09
$986/nighttotal: $4930 (5 )

Beach Family Time Enjoy The Backyard Pool And Sunroom

3 4
apartment, Virginia Beach
This three-bedroom apartment in Virginia Beach is conveniently located just minutes from the beach and waterways, with easy access to Interstate 64. It has received very good ratings from previous guests and is ideal for families and groups.
The 260 square metre apartment comfortably sleeps up to 10 guests and comes with a range of amenities including a private pool, sunroom, top-deck bath, and a garden. Guests can enjoy activities such as jet skiing, kayaking, cave exploring, and mountain biking, as well as exploring the nearby cultural attractions and family-friendly activities.

Best Chesapeake, VA vacation rentals with air conditioning

Charming Quiet Carriage House - Chesapeake, VA
10 35 reviews
Chesapeake, VA
31/07 – 31/08
$158/nighttotal: $4898 (31 )

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.
Bright & Cozy Condo Near Everything - Chesapeake, VA
Chesapeake, VA
29/06 – 03/08
$199/nighttotal: $6965 (35 )

Bright & Cozy Condo Near Everything

1 2
apartment, Virginia Beach
This two-bedroom, two-bathroom condominium is centrally located in Virginia Beach, offering convenient access to shopping, dining, and local attractions.
This bright and airy apartment features vaulted ceilings, a skylight, and a fully equipped kitchen, accommodating up to four guests with in-unit laundry and reserved parking.
Charming Efficiency! - Chesapeake, VA
9.8 51 reviews
Chesapeake, VA
14/08 – 16/08
$274/nighttotal: $548 (2 )

Charming Efficiency!

1 2
apartment, Chesapeake
This Chesapeake flat boasts a central location offering easy access to major attractions such as Virginia Beach, Colonial Williamsburg, and Busch Gardens, with convenient interstate connections.
The self-catering studio apartment sleeps two, features a queen-size DreamCloud Premier mattress, 50" smart TV, full bathroom, and stainless steel appliances, and is close to various seafood restaurants and historical sites including the Battleship Wisconsin and the Hampton Roads Naval Museum.
3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia. - Chesapeake, VA
10 47 reviews
Chesapeake, VA
25/09 – 30/09
$321/nighttotal: $1605 (5 )

3-bedroom Home Away From Home In Fabulous Chesapeake, Virginia.

3 2
apartment, Chesapeake
This three-bedroom Chesapeake house, located in the Great Bridge area, is 14 kilometres from Naval Station Norfolk and 39 kilometres from Virginia Beach's seafront.
The 148-square-metre property offers a king-size bed, a queen-size bed, and flexible twin beds (convertible to a king), accommodating up to six guests, and includes a full kitchen, washer/dryer, Wi-Fi, and a screened patio with a large fenced garden.
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