Condo vacation rentals in Chesapeake

Find and book unique condos on Airbnb

Top-rated condo rentals in Chesapeake

Guests agree: these condos are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Williamsburg

4.95 out of 5 average rating, 129 reviews

Kingsmill 1bed/1ba on Golf Course 9th Fairway

This beautiful 1 bed-1 bath unit is a cozy 400 sq.ft. and is located in the exclusive Kingsmill neighborhood. This first floor unit offers a king-size bed with a private patio that walks out onto the 9th Fairway of the River Course at Kingsmill. You'll enjoy the luxurious full bathroom with shower/tub combination and upgraded finishes. In the bedroom, you'll also find a computer desk, an over-sized sitting chair, a mini-fridge, a microwave, a Keurig coffee maker, and 50" Roku Smart TV w cable!

Aug 31 – Sep 7

G$32,270 GYD per night

Guest favorite

Condo in Williamsburg

4.94 out of 5 average rating, 105 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Feb 20 – 27

G$45,517 GYD per night

Guest favorite

Condo in Virginia Beach

4.93 out of 5 average rating, 244 reviews

2 bedroom condo with oceanfront one block away!

Come enjoy everything Virginia Beach has to offer. Our cozy condo has all of the comforts of home and is perfect for families and accommodates 6 adults. Bedroom 1 has a king size bed w/TV, bedroom 2 has a queen size bed w/TV and the living room has a sofa that pulls out into a full size sofa bed w/TV. The Boardwalk, Shopping, Restaurants, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach!

Sep 9 – 16

G$55,138 GYD per night

Guest favorite

Condo in Virginia Beach

4.88 out of 5 average rating, 176 reviews

Oceanfront Gem VaB Studio Exceptional Views

Newly renovated modern studio condo, owners personal getaway now open to guests. This corner unit, the largest and most private in Oceans ll Condominium complex, is on the 3rd floor and offers beautiful, expansive views at both sunrise and sunset. Just off the boardwalk with community pool, this unit sleeps three. Right on the oceanfront, you won't find a more peaceful getaway! Beach chairs and towels provided. Please note: due to the open layout of the building, there is no elevator.

Jan 14 – 21

G$37,573 GYD per night

Guest favorite

Condo in Virginia Beach

4.83 out of 5 average rating, 101 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, master bedroom. Watching ocean waves, sunrise/moonrise, dolphins swimming by. Enjoy the ocean, boardwalk, beach gym, beach playground right downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, stores, bars, beach concerts. New 65” smart QLED TV in living room, new sofa, new dining room set. Up to 45% off Winter Special Deals!

Oct 21 – 28

G$116,563 GYD per night

Guest favorite

Condo in Virginia Beach

4.94 out of 5 average rating, 103 reviews

Airy 2BR Beach Blessing Condo Near Rudee Inlet

This spacious 2 bedroom (each with en-suite baths) 2.5 bath condo is near Rudee Inlet and all oceanfront activities. Simply walk across the street & relax on the beach, dine at great restaurants, walk under the bridge next to the city parking lot to enjoy all the water activities that originate from Rudee Inlet (i.e. Dolphin/Whale Watching Tours, Sunset cocktails), or relax on the balcony. *Discounted/ Seasonal rate Oct-Feb Check beacheventsvb for upcoming events

Apr 13 – 20

G$43,095 GYD per night

Guest favorite

Condo in Virginia Beach

4.86 out of 5 average rating, 207 reviews

Ocean Escape

Ocean Escape, 4th floor condo in the luxuriously upscale Sanctuary Resort at False Cape in Virginia Beach, Virginia, breathtaking views of both the Atlantic Ocean and Back Bay and is a leisurely 100 step stroll to the beautiful beach and surf. Beach chairs, coolers, umbrellas, sand toys for the kids, boogie boards and two beach cruiser bikes. Expansive community pool area, complete with Jacuzzi tub, lounge furniture, stainless steel gas grills and picnic tables.

Oct 17 – 24

G$35,591 GYD per night

Guest favorite

Condo in Virginia Beach

4.94 out of 5 average rating, 253 reviews

Beach Condo Block Off Boardwalk

Come enjoy everything Virginia Beach has to offer. Our condo has all of the comforts of home and accommodates 4 adults or perfect for families. Bedroom has a king size bed and living room has sofa that pulls out into a full size sofa bed. TVs in both rooms. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family. Come have a relaxing and fun vacation at the beach.

May 20 – 27

G$48,070 GYD per night

Guest favorite

Condo in Virginia Beach

4.9 out of 5 average rating, 182 reviews

Va Beach Oceanfront Studio, Boardwalk, Pool, Beach

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Nov 14 – 21

G$33,524 GYD per night

Guest favorite

Condo in Virginia Beach

4.93 out of 5 average rating, 196 reviews

2 Bedroom Condo ONE Block from the Oceanfront

Come enjoy a Virginia Beach vacation ONE block from the oceanfront and boardwalk. Our 2 bedroom condo accommodates 4 adults and is also perfect for families. Bedroom 1 has a queen size bed and bedroom 2 has a king size bed. There is also a pull out sofa bed in the living room. The Boardwalk, Shopping, Restaurants, Amusement parks, and many more activities are all within walking distance. There is plenty to do for the whole family.

Sep 29 – Oct 6

G$56,059 GYD per night

Guest favorite

Condo in Virginia Beach

4.85 out of 5 average rating, 109 reviews

NEW! Beach Paradise Studio on the Boardwalk w/Pool

Enjoy a piece of the Oceanfront with this gorgeous updated condo! Walk out your front door to the beach, pool, boardwalk, the historic Cavalier hotel, restaurants, shops and many entertainments on the beach! Newly renovated, this beachy North End paradise is the perfect getaway for a couple. One parking spot, deck area , a lawn on the beach with lounge chairs and coin operated laundry available on premises.

Sep 24 – Oct 1

G$41,934 GYD per night

Guest favorite

Condo in Newport News

4.9 out of 5 average rating, 127 reviews

Cozy Home Away from Home at Mary Robert Lane

Bring the whole family to this great place with lots of room for fun. Less than 10 minutes away from Fort Eustis Military Base. Less than 15 min away from Newport News Airport, Christopher Newport University, and plenty of shopping and dining. Short drive to Williamsburg with shopping at the outlet mall, dining and entertainment for the family at Busch Gardens and Water Country USA theme parks.

Mar 5 – 12

G$31,972 GYD per night