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Apartment holiday rentals in Chesapeake

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Top-rated apartment rentals in Chesapeake

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Flat

4.89 out of 5 average rating, 102 reviews

Close 2 East Beach, EOV, King Bed, Top Floor

Come relax and unwind at Max’s at 14th bay Apartment! Located only TWO blocks from the beach in the quiet East Oceanview neighborhood of Norfolk! It is the ideal getaway for families and the modern traveler. The apartment is on the third (TOP) floor and each bedroom is outfitted with a comfy memory foam mattress (1 king and 1 queen), work desk, and smart TV. In addition, there is high speed internet, washer and dryer. It is conveniently located minutes from restaurants, grocery stores, and brew

Guest favourite

Flat

4.91 out of 5 average rating, 515 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 500 mbps Wifi, internet tv. Futon-like couch.

Guest favourite

Flat

4.96 out of 5 average rating, 114 reviews

"The Ponderosa B" - Close to the Casino

Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, nice family oriented neighborhood about 1/2 mile Rivers Casino! - Get ready for great upcoming Concerts, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

Guest favourite

Flat

4.94 out of 5 average rating, 109 reviews

Large Apartment Near Busch Gardens & Military Base

Bring the whole family to this fantastic place that offers ample space for fun, along with a nearby playground in the neighborhood. This two-story home features a living room, dining room, kitchen, and laundry facilities on the ground floor, while the bedrooms are located upstairs. You can enjoy cooking, creativity, relaxation, and a wonderful vacation while visiting the Williamsburg, VA area. Busch Gardens is just a 5-minute drive away, and the military base is only 15 minutes away by car.

Guest favourite

Flat

4.96 out of 5 average rating, 268 reviews

Cozy Ground Floor Apt in Historic Home

Charming 1st floor apartment with private entrance in circa 1795 home in the Olde Towne historic neighborhood. Guests enjoy an easy walk to downtown shops, restaurants, breweries, museums, and a movie theater. The waterfront is close with marinas, restaurants, and the Elizabeth River ferry to transport you to Norfolk to enjoy events on the waterfront. Business or military travelers are two blocks from the Renaissance Hotel and a 15-minute walk from the Portsmouth Naval Hospital.

Guest favourite

Flat

4.85 out of 5 average rating, 100 reviews

2BR Haven: Modern Comforts, Timeless Charm

Welcome to our cozy 2 bedroom, 1 bathroom apartment located in the heart of the city, just steps away from the best restaurants, shops, and entertainment options. Our charming space features a fully equipped kitchen, comfortable living area with a pull-out sofa, and a bathroom with fresh towels and toiletries. With its convenient location near Buckroe Beach, our apartment is the perfect home base for your next vacation. We strive to provide our guests with the best possible experience.

Guest favourite

Flat

4.9 out of 5 average rating, 145 reviews

Spacious Recently Renovated Apartment

Fantastic freshly renovated roomy apartment smack in the heart of the Ghent district. Just a few minutes walk from EVMS, ODU, numerous neighborhood craft breweries and an endless variety of dining options, including the area's only authentic wood-fired oven bakery, several locally owned coffee houses and organic stores. The area's best supermarket is also one block away (Fresh Market) and the brand new Aldi is also just a few more steps down the street. Due to allergies-no pets. Sorry.

Guest favourite

Flat

4.94 out of 5 average rating, 102 reviews

Lovely Two Bedroom, 1 1/2 bath, King bed Townhouse

Your family will be close to everything when you stay at this centrally-located place. Beautiful re-done townhouse. New carpet and luxury vinyl, new vanities and toilets, Maytag washer and dryer, central heat and air, brand new hot water tank, small patio in back. Close to shopping, Kroger, T J Maxx, Walmart, CVS, and other shops. Plenty of take out food, like chick-fil-A, Panda Express, Wendys, Rallys, Dunkin Donuts, and more. Brand new Rivers Casino less than a mile away!

Guest favourite

Flat

4.96 out of 5 average rating, 114 reviews

Best location in Olde Towne Portsmouth

This apartment is available for up to 6 months upon request. Perfect location for traveling medical professionals. Very convenient to the Naval Medical Center. Enjoy Historic Old Towne and stay in a home built in 1850. Stroll the neighborhood where you will see houses from the late 1700's. Take a short walk to numerous restaurants or take in a movie at the historic Commodore Theater. Two blocks away is the ferry terminal to Waterside in downtown Norfolk.

Guest favourite

Flat

4.91 out of 5 average rating, 216 reviews

VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool

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

Guest favourite

Flat

4.88 out of 5 average rating, 133 reviews

Penthouse Paradise On The Harbor

Enjoy a stylish experience at our brand new, centrally-located , downtown penthouse suite. This property, directly overlooking the historic Docks @ Downtown Hampton features many attractions such as Virginia Air and Space Science Center, Hampton Coliseum, Buckroe Beach and Park. This space is also located within walking distance of many quaint restaurants and speakeasy's such as Pour Girls, Marker 20, Baked Bistro and Pizza, and Stillwater Tavern.

Guest favourite

Flat

4.92 out of 5 average rating, 103 reviews

Charming cozy apt historic in Old Towne Portsmouth

Newly renovated, newly furnished, cozy and relaxing 1 bd 1 bath apt is available for your stay. Coffee shops, museums, restaurants, bars and the Commodore Theater are all within steps. The ferry to downtown Norfolk is a quick 5 minute walk and every Saturday morning the Farmers Market is literally around the corner. If you are in town for a concert, the Amphitheater is a short walk away. Let us make your stay stress free and enjoyable.

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Popular amenities for Chesapeake apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Guest favourite

Flat

4.96 out of 5 average rating, 74 reviews

North End Beach Cottage Apt - One Block from Beach

Flat

4.9 out of 5 average rating, 105 reviews

Sojourn Guest House: Buckroe Beach Suite B

Guest favourite

Flat

4.96 out of 5 average rating, 28 reviews

2 Bdrm Condo 1 block from VB Oceanfront

Guest favourite

Flat

4.88 out of 5 average rating, 68 reviews

Comfy 3 Bedroom Hideaway Minutes From H.U. & Beach

Guest favourite

Flat

4.91 out of 5 average rating, 34 reviews

Quaint Quarters Oceana

Flat

5 out of 5 average rating, 4 reviews

Bay Haven - Suffolk Suite

Guest favourite

Flat

4.83 out of 5 average rating, 47 reviews

Portsmouth Coastguard --Large 3 Room Apartment

Guest favourite

Flat

5 out of 5 average rating, 40 reviews

Granny-Chic Suite: King Bed & Washer/Dryer

Private apartment rentals

Guest favourite

Flat

4.95 out of 5 average rating, 21 reviews

Serene Tree House Retreat | Spacious 1br/1bth Home

Guest favourite

Flat

5 out of 5 average rating, 55 reviews

Entire Apartment - No Cleaning Fees!

Guest favourite

Flat

4.98 out of 5 average rating, 96 reviews

English Basement Hide-Away

Guest favourite

Flat

4.92 out of 5 average rating, 26 reviews

Private Beach Suite

Guest favourite

Flat

4.96 out of 5 average rating, 26 reviews

Sandbridge Beach Bay Getaway

Guest favourite

Flat

5 out of 5 average rating, 7 reviews

Beach Oasis- Apartment steps from the sand!

Guest favourite

Flat

4.99 out of 5 average rating, 191 reviews

Elegant Cozy Colonial/Private/Self Check-in

Flat

4.75 out of 5 average rating, 12 reviews

Georgie's Brick Air BNB

Apartment rentals with a hot tub

Flat

5 out of 5 average rating, 3 reviews

Full Kitchen Secure Bike Racks

Flat

4.83 out of 5 average rating, 122 reviews

Poseidon - 120 Year Old Beach Cottage with Sauna

Flat

4.75 out of 5 average rating, 8 reviews

Virginia Beach Oceanfront Condo

Guest favourite

Flat

5 out of 5 average rating, 20 reviews

Sunset Retreat

Guest favourite

Flat

5 out of 5 average rating, 25 reviews

Bayside condo on the beach in Sandbridge

Quick stats about flat rentals in Chesapeake

Total rentals
160 properties
Nightly prices starting at
£8 before taxes and fees
Total number of reviews
5.4K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool

Destinations to explore