
Condo vacation rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: these condos are highly rated for location, cleanliness, and more.

Tropical 2BR Condo Getaway 1 Block from the Beach!
Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

Ocean & Bay Views - Local Family Owned & Operated
Just steps away from the sand, "Carolina on My Mind" is a 2b/2ba oceanside condo at the exclusive Sanctuary at False Cape, the only Oceanfront complex at Sandbridge in Virginia Beach. You'll enjoy a private patio with both Ocean and Bay views and you'll have access to all the exclusive amenities of the complex. The condo features a large open-concept living space and a fully equipped gourmet kitchen. The master has a king bed, the second bedroom has king bed w/ twin loft. Queen sleeper sofa.

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. Community pool area, complete with Jacuzzi tub, lounge furniture, and stainless steel gas grills. The elevator is just across from dedicated parking spot.

Spacious Captain’s Beach Suite Near Rudee Inlet
Take advantage of the seasonal rates plan a winter escape to the beach! Don’t miss all the wonderful holiday activities to include the holiday lights, holiday parade & more! This spacious beautifully decorated 2-bedroom (each with ensuite baths) condo is near Rudee Inlet and all oceanfront activities. 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.

2 Bedroom Condo One Block from the Oceanfront!
Our newly renovated 2 bedroom condo ONE block from the boardwalk accommodates 6 people and is also perfect for families. Each bedroom has a flat screen TV; one with a queen bed and the other with a king bed. There is also a pull out sofa bed in the living room along with a large TV. This is a 2nd floor unit with one designated parking spot. Plenty to do for the whole family with the beach, boardwalk, shopping, restaurants, amusement parks, and many more activities all within walking distance.

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 and you can walk to the beach in 3 minutes or less! Come have a relaxing and fun vacation at the beach.

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!

Beach Chic Remodeled Condo 1 Block from Beachfront
If a get-away is what you need, then simply "My Beach Hideout’ is what you want. Completely renovated 2 Bedroom/1 Bath condo a short one-block walk from the oceanfront. Enjoy a stylish, relaxed coastal-vibe experience. Perfectly comfortable for 4 guests or a solo long-business stay. Dining, nightlife, entertainment, events, VB boardwalk & shops all within walking distance. Immaculate condo has queen bed + TV in both bedrooms, living room, stocked kitchen, bath + parking.

Walk to beach BEAUTIFUL 2BR 1BA condo
1 block to Ocean/Boardwalk on 9th and Pacific in the heart of resort town. Beautifully furnished, 600sq ft beach-themed condo. Beds sleep 4 (1 Q, 2 Twin) and comfortable sleeper sofa adds 2 more. Also close to Convention Center, Vibe District, new Sports Complex. Perfect for family w/children or 4 adults. Free parking for 1 vehicle in front of unit. Spend a min 2 nights Sept-May and stay a week from early June to Labor Day (summers days are Sat-Sat rental).

VB Condo,Boardwalk/Oceanfront,Beach, Pool,Kitchen
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

Walk to beach lovely 2/2 in "Kingsmill on James"
Lovely, quiet, large ground floor 2 bdrm 2 full bath condo in "Kingsmill on the James". Beautiful tree and Audubon bird sanctuaries, trails. Condo backs to greenbelt, within walking distance to Kingsmill's beach, spa, marina, Café. **please note condo is in "Kingsmill on the James", not Kingsmill Resort...there's spa and beach access, for dogs too, but not pool... to use pool and resort, please book directly through the resort

*Mid/Long Term Rental* Cozy Home at Mary Roberts
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.
Popular amenities for Chesapeake condo rentals
Weekly condo rentals

Blue Ocean Getaway

OBC - 1BR/1BA - Amazing Oceanfront View!

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!

Charming 1BR Colonial Condo at Wyndham Kingsgate

21st Street Condo - 1 block from the Dome

Coastal Beach condo-amazing view and indoor pool

Prime Location: Steps to Beach & Attractions

Cozy 2BR Condo in Williamsburg
Pet-friendly condo rentals

2 bdr: Steps to Sand, Dog-Friendly!

Cozy & Fun Hampton Condo, WIFI & W/D! Dogs welcome

Ocean Bliss: Cozy Apt Retreat(D)

Toes In The Sand! 2 Bed 2 Bath and Dog Friendly

Oyster & Pearl Beautiful New Single Level Condo

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Beachfront Getaway, Pet Friendly, Dolphin Suite

NEW! Prime Location @Beach Club -Tranquil Seascape
Condo rentals with a pool

Cher's Place @ The Beach

Sandbridge Beach - DeepSeaSide Retreat

Good Vibes at the Beach

1-Bedroom Condo in Williamsburg, VA

Marriott Manor Club Luxury Studio sleeps 4

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Oceanfront - Balcony Views - Walk to Beach & Shops

Wonderful & tranquil beach retreat: 2BR/2BA Condo.
When is the best time to visit Chesapeake?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,003 GYD | G$23,003 GYD | G$22,793 GYD | G$22,375 GYD | G$21,957 GYD | G$21,330 GYD | G$21,121 GYD | G$21,539 GYD | G$22,793 GYD | G$23,212 GYD | G$26,139 GYD | G$23,212 GYD |
| Avg. temp | 6°C | 7°C | 10°C | 16°C | 20°C | 25°C | 27°C | 26°C | 23°C | 18°C | 12°C | 8°C |
Quick stats about condo rentals in Chesapeake

Total vacation rentals
Explore 40 vacation rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at G$10,456 GYD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesapeake vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

4.8 Average rating
Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Chesapeake's top spots, include Chrysler Museum of Art, Nauticus, and Cinemark Chesapeake Square
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- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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- Corolla Beach
- Water Country USA
- First Landing State Park
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