Some info has been automatically translated. Show original language

Cottage vacation rentals in Chesapeake

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Chesapeake

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

%{current} / %{total}1 / 1
Top guest favorite
The front entrance features a ramp leading to a bright blue door surrounded by large windows. The white exterior of the house is complemented by landscaping with green shrubs and a sunny sky overhead, enhancing the welcoming appeal.
Cottage in Virginia Beach
4.97 out of 5 average rating, 206 reviews

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.

Top guest favorite
A cheerful cottage is framed by tall trees and surrounded by a spacious lawn. The front porch features white railings and a welcoming green door. A mailbox stands at the edge of a quiet road, highlighting the tranquil neighborhood setting.
Cottage in Sunbury
4.97 out of 5 average rating, 134 reviews

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.

Top guest favorite
A serene sunset view is captured over the Elizabeth River, with vibrant hues of orange and pink filling the sky. Silhouetted trees frame the scene, while a peaceful dock extends into the water, inviting moments of reflection and tranquility.
Cottage in Norfolk
5 out of 5 average rating, 290 reviews

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

Guest favorite
A bright sunroom features large windows that frame views of the Chesapeake Bay and surrounding natural landscape. Light-colored furnishings complemented by a wooden coffee table and a small plant enhance the airy feel. The serene atmosphere is accentuated by sunlight streaming through the glass.
Cottage in Norfolk
4.99 out of 5 average rating, 161 reviews

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.

Top guest favorite
The waterfront view captures a serene sunset over the canal, with soft golden light reflecting on the water. Lush grasses and reeds line the shore, enhancing the tranquil atmosphere. Nearby homes are silhouetted against the vibrant sky, creating a peaceful retreat.
Cottage in Sandbridge
5 out of 5 average rating, 111 reviews

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.

Top guest favorite
A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.
Cottage in East Ocean View
4.99 out of 5 average rating, 293 reviews

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.

Top guest favorite
A cozy living area is furnished with two light blue sofas and a light-colored area rug. A ceiling fan hangs above, providing air circulation. In the background, a dining area with a wooden table and blue chairs is visible through an arched entryway, framed by bright natural light from window blinds.
Cottage in Norfolk
4.93 out of 5 average rating, 142 reviews

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.

Top guest favorite
Cottage in Norfolk
4.97 out of 5 average rating, 278 reviews

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.

Top guest favorite
A serene waterscape is presented, highlighting the cottage set among lush trees. A dock extends into the water, flanked by boats, with soft ripples reflecting the clear blue sky. The tranquil environment suggests a peaceful retreat by the water's edge.
Cottage in Gloucester Point
4.99 out of 5 average rating, 161 reviews

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.

Guest favorite
A serene view of a wooden dock extending into the calm waters of Sarah's Creek, surrounded by trees. Two kayaks, one green and one blue, are positioned on the grassy shore, with a charming cottage visible in the background.
Cottage in Gloucester Point
4.94 out of 5 average rating, 309 reviews

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.

Guest favorite
A spacious dining area is highlighted by a wooden table surrounded by six white chairs. A chandelier with warm yellow bulbs illuminates the room. A world map is displayed on the wall, while large windows allow natural light to fill the space.
Cottage in Willoughby
4.88 out of 5 average rating, 117 reviews

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!

Guest favorite
A charming blue beach house features a multi-level design with large windows that invite natural light. A spacious deck offers unobstructed views of the surrounding sandy landscape. Steps lead up to the entrance, enhancing accessibility to the home. Wild grasses frame the property.
Cottage in Corolla
4.89 out of 5 average rating, 160 reviews

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

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

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake
  5. Cottage rentals