
Cottage vacation rentals in Chesapeake
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Top-rated cottage rentals in Chesapeake
Guests agree: these cottages are highly rated for location, cleanliness, and more.

The Seaglass Cottage by the Chesapeake Bay
The Seaglass Cottage by the Bay is located in the charming & beautiful neighborhood of Ocean Park just a quick 5-10 minutes stroll to the Chesapeake Bay beach. Our vintage beach house from the 1940’s has been fully remodeled and decorated in local art and beach décor. There are beautiful live oaks on the property and 3 private parking spaces for you and some first-come-first-serve street parking in front of the house. Easy load in with a ramp into the house and a mudroom for all your beach toys.

The Little House on Park Avenue
Our cottage is a quiet get-away. Sit on the front porch and enjoy the birds and a cup of coffee. Small kitchen provides everything you may need for your stay, including a local yummy treat. A desk in the bedroom gives you a place to work while others in your group utilize the spaces in the living room or dining room. You can leisurely stroll by the Ruritan Park to Studio 32 Gallery and Gift shop on weekends. In 10 minutes drive to Merchants Millpond State Park. Historic Edenton only30 minutes.

Beautiful Cottage Waterfront Near Downtown Norfolk
A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

Beach Front with Paddle Boards and Kayaks
You have your own private access to the beach AND water views of the Chesapeake Bay that no other home in the area has. The sunrises and sunsets are breathtaking! Paddle boards and kayaks are provided. My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

Sanctuary on Sandpiper - Bayfront in Sandbridge
Relax in this renovated 1950's flat-top beach cottage in gorgeous Sandbridge Beach. This waterfront home, on a canal off the beautiful Back Bay, is an easy five-minute, two-block walk to the ocean and the perfect setting for your family beach vacation. With three king beds, a custom-built bunk room, two full baths, a well-equipped kitchen, a spacious backyard, saltwater pool, and all linens and beach gear included, it's got everything you need to spend quality time away with your family.

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Cozy Cottage w/ Hot Tub, Pool Table, Fenced Yard
Welcome to Wayland Beach Cottage, a relaxed beach retreat with your own private hot tub and separate game room. Unwind under the pergola, soak year-round in the 6-person hot tub, or enjoy movie nights and friendly competition around the full-size 8-foot pool table in your own entertainment space. With a fully fenced yard, smart TVs throughout, fast Wi-Fi, a long private driveway, and easy access to beaches and dining, it’s the perfect getaway for families and friends.

Positano Villa
This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Sarah's Creek Starlight
Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

The Cottage on Sarah's Creek
Nestled on the waters of Sarah's Creek, this cozy cottage is just a short drive from historic Williamsburg and Yorktown. Fully furnished with a new kitchen, dining area, 1 bedroom, 1 bathroom, and a large loft with a queen bed and a pool table. Whether spending your days relaxing on the beach, exploring historic sights, or taking a tour of a local vineyard, you can look forward to the quiet comfort this cottage has to offer during your stay.

Coastal Modern Cabin
Your coastal and modern beach getaway, with everything you need for a great stay! Discover: Across the street from the beach Huge back porch Two egg chairs Air hockey Electric fireplace 75" TV with subscriptions Retro arcade games Board games Bag toss Secluded beach access, no large crowds! Check out the picture descriptions! With 100+ views a day, a guest is on the way! So, book now and enjoy your stay at the Coastal Modern Cabin!

Horses-Views-Dog Friendly-4WD Area
Break’n Wind is a cute and cozy 3 BR/3 BA beach house located on the pristine beaches in the 4-Wheel Drive area of Corolla, NC, also known as Carova. Beautiful views! Wild horses roam free & will visit you at the house! Really! Located off road in 4-Wheel Drive area. Your vehicle must have 4WD or AWD with high clearance to get through high sand. No paved roads.
Popular amenities for Chesapeake cottage rentals
Cottage rentals with a hot tub

Kasita Barceló •Ht’d Pool HotTub Near Beach Slps10

Beautiful 1 Bedroom @ Kingscreek Resort

902C Coastal King Retreat Steps from Beach + Sauna

1-Min walk to Beach! Ocean Views, Hot Tub

Beautiful Obx Home W. Pristine Views

Jul 18-25 3-bdrm Williamsburg Kings Creek Resort

Coastal Cottage, heated pool, resort community

902 B Historical Beachfront Duplex Sauna & Hot Tub
Pet-friendly cottage rentals

The Ladybug - arcade, dog-friendly, firepit, & EV

Comfy three bedroom cottage - easy beach access

Saltwater Seaclusion- Corolla-Walk to Everything!

Key Lime Cottage - Your Beachside Retreat

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Dog friendly, large fenced yard! 1st Floor Bedroom

Quaint Beach Cottage in 4WD-OBX

Quaint 2 Bedroom Cottage in Chicks Beach
Private cottage rentals

60 Seconds 2 Beach (Duplex 2 of 2)

Vintage Cottage on Private Creek–Near Beach & Base

Life on a Sandbar right on Chesapeake Bay

Colonial williamsburg house

“Magnolia Cottage” on the River

Vintage Beach Cottage by the Chesapeake Bay

Private, quaint cottage in Historic Yorktown

WhimSea~2BR Cottage~Backyard Oasis~Luxury Bathroom
Quick stats about cottage rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 560 verified reviews to help you choose

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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- Cottage rentals Virginia
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Cape Charles Beachfront
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- Colonial Williamsburg's Merchants Square
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