
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.

ManeStay Island Beach Cottage - Wild Horses Roam
Embrace the untethered vibes of Modern Island Retreat along 11 mile barrier island Ocean coastline where wild horses roam free. Ideal for romantic couples getaway, honeymoon or to reconnect with your inner writer, photographer, artist or nature enthusiast. Bring a good book for the hammock or shower outdoors and relax under the stars. Getting here is part of the adventure – 4WD vehicle needed to drive down the ocean beach... Reliable Wi-Fi, Internet and Roku TV. Beach parking pass included

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

Cozy Cottage - NEW hot tub, dogs OK, fenced yard
Welcome to Wayland Beach Cottage, your home away from home! Here are some of the things you can look forward to: - queen beds - smart TVs in each room - fully equipped kitchen & laundry room - fully fenced backyard - 6-person hot tub *new!* - outdoor seating under a pergola - 4-burner gas grill - long, private driveway - speedy Wi-Fi We're nearby to so many fun things to do, shop, and eat! Bring the family, see the sights, and come relax at Wayland Beach Cottage. We'd love to have you!

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.

Carriage House at the Historic Church Point Manor
Relax in the luxurious Carriage House: a 3-bedroom French-country style retreat at the historic Church Point Manor (circa 1860). Restored in 2021 with modern amenities, the Carriage House features a king bedroom and two queen bedrooms, each with its own private, full bathroom. Enjoy our private nature trail, tennis court, and lush gardens. The Manor has hosted some of Virginia Beach’s most VIP guests, including President Obama, and is also listed on the city's Historic Register.

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!

Nostalgia, WATER front Dream escape w/pier
Cozy WATER FRONT getaway with screened porch, pier, BEACH and open concept living situated on the banks of the Chowan river. Quiet, Serene location 12 miles outside historic downtown EDENTON on the Chowan River. Enjoy the beautiful sunsets and tranquil mornings on the River. Kayak available for guest use. Enjoy RELAXING by the fire pit roasting marshmallows while enjoying the MOST BEAUTIFUL sunsets!
Popular amenities for Chesapeake cottage rentals
Cottage rentals with a hot tub

Horses-Views-Dog Friendly-4WD Area

Kasita Barceló | Pool, HotTub, Near Beach, Slps 10

Beautiful 1 Bedroom Penthouse @ Kingscreek Resort

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

Jul 18-25 $1800 3-bedroom Williamsburg

Old Bay Hideaway Oceanfront Cottage 4 bdrm, 2 bath

Coastal Cottage, heated pool, resort community

Waterfront Gloucester Cottage w/ Private Boat Dock
Pet-friendly cottage rentals

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

Historic 3BR • Xmas Ready • First Firewood On Us!

Cooter's Cabin

Cozy North Duck Beach Cottage – Walk to Beach + Pr

Comfy three bedroom cottage - easy beach access

Saltwater Seaclusion- Corolla-Walk to Everything!

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Quaint Beach Cottage in 4WD-OBX
Private cottage rentals

Riverfront Oasis | Kayaks, Private Beach, & More

Secluded, water views, private pool, 1 mi to beach

Beach Music Chesapeake Bay Getaway for all Seasons

Private, quaint cottage in Historic Yorktown

Key Lime Cottage - Your Beachside Retreat

Carova Beach Crash Pad

Vintage Beach Cottage by the Chesapeake Bay

WhimSea
Quick stats about cottage rentals in Chesapeake

Nightly prices starting at
Chesapeake vacation rentals start at € 87 per night before taxes and fees

Verified guest reviews
Over 390 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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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Carova Beach
- Buckroe Beach
- Corolla Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
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