Vacation home rentals near Chesapeake Bay

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Top-rated vacation home rentals near Chesapeake Bay

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

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Guest favorite
The exterior of a blue, single-story home is presented, featuring a welcoming front porch with white railings. The front yard is landscaped with shrubs and flowers. A charcoal grill is positioned on the right, and ample parking space is visible in the driveway.
Vacation home in Frankford
4.89 out of 5 average rating, 72 reviews

Charming Beach/Bay Escape with Activities for All!

There's much to do from our comfortable and clean Ocean View vacation home! The beautiful Delaware beaches are a given (10 minute drive to Bethany depending on traffic.) But within a short drive there's fishing, crabbing, hiking, kayaking, golf, putt-putt and more. Just minutes to shopping, antiquing, outlet malls, and superb restaurants. Home amenities as well: large yard, game room, hammock and swings, grill, etc. The very low traffic, private road loops offer safe jogging and biking. Enjoy!

Guest favorite
A welcoming home features large windows overlooking a glistening pool, which invites relaxation. Several lounge chairs are positioned around the pool area, and an umbrella provides shade. The wooden deck extends from the house, enhancing the outdoor space.
Vacation home in Burgess
4.89 out of 5 average rating, 18 reviews

Northern Neck Waterfront

Relax with the whole family at this peaceful waterfront retreat. Nestled along Coles Creek and the Great Wicomico River, this 3-bedroom house is a perfect waterfront getaway with all the amenities you need for a comfortable stay. Savor the beauty of nature from our backyard, where a glistening pool takes center stage, inviting you to unwind and bask in the sun. If you're an aquatic enthusiast or simply someone in search of serenity, our house in Burgess offers an idyllic haven to vacation.

Top guest favorite
The open living area features a cozy seating arrangement with a plush sofa and armchairs, complemented by a rustic wooden dining table that seats six. A flat-screen television is mounted on the wall, and a decorative plant adds a touch of greenery.
Vacation home in Washington
4.99 out of 5 average rating, 105 reviews

Designer apt with high end finishes and furnishing

Located in a large, historic townhouse in the Historic District near Lincoln Park and the Eastern Market this professionally decorated English basement apartment includes original artwork; designer furnishings chosen for comfort; and an open concept living/dining/kitchen accented by a rustic antique dining table that seats up to 6. Lush front garden with cafe' table and seating for 6. The new bathroom features double sinks, lighted medicine cabinets and an extra-large shower. Parking permit..

Guest favorite
A seasonal outdoor pool is surrounded by a sunlit concrete patio, featuring a stone border. White lounge chairs are positioned nearby, with a gas grill visible in the background, set against a backdrop of mature trees and greenery.
Vacation home in Fredericksburg
4.9 out of 5 average rating, 87 reviews

Cheerful 3 bedroom home with a pool and sauna

Tucked next to the Frederal civil war park in very quiet 2 acres land at a dead end street but very close to the historic Fredericksburg downtown (In 2026, the pool opens on May 22nd). You can take 5 minutes short walk to access the civil war park and enjoying more than 10 miles of historical beautiful federal civil war park land. Or you can just stay in the house and relax with the tranquility or the sauna. Or visit the historical Fredericksburg downtown or George Washington boyhood home.

Top guest favorite
A comfortable living area boasts a gray sofa adorned with bright yellow decorative pillows. A wooden coffee table rests in front of the sofa, complemented by an antique trunk nearby. The warm yellow walls are accented with artwork and natural wood doors, creating a welcoming environment.
Vacation home in Milton
5 out of 5 average rating, 47 reviews

Serene Cozy Couples Getaway

Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

Top guest favorite
A compact in-law suite is displayed, featuring a full kitchen with stainless steel appliances. A comfortable pull-out couch sits adjacent to a wooden coffee table on a patterned rug. A small dining table with two chairs is present, along with a stacked washer and dryer.
Vacation home in Washington
4.96 out of 5 average rating, 285 reviews

In-Law Suite in Van Ness/Cleveland Prk/free parkin

Bright new in-law suite with a separate entrance, full kitchen, washer & dryer, fast internet, pull-out couch, laptop desks, and a pack n' play for little ones. Easy access to National Mall via Van Ness metro stop four minutes away. Flexible check in and check out, no cleaning fees (though smoking, marijuana and incense are a firm no). We've been hosting people from all over the world for several years, and we're happy to help you have a great time in Washington, for leisure or work!

Top guest favorite
Vacation home in Severna Park
5 out of 5 average rating, 46 reviews

Waterfront 5 Bedroom Home Close to Annapolis

Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Top guest favorite
The exterior of a two-story garage apartment is shown, featuring beige siding and contrasting dark shutters. A distinctive teal sign is mounted above the entrance, while two white garage doors are visible at the base. A tree with green leaves is partially displayed on the right.
Vacation home in Ocean City
4.98 out of 5 average rating, 53 reviews

Vacay Stay-2BR/1Bath, Family Groups Only

Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Top guest favorite
Vacation home in Gettysburg
4.97 out of 5 average rating, 100 reviews

New The Ridge is a Cozy 2-bedroom apartment

The Ridge is a Cozy 2 Q Bedrooms, 1 bath with walk in shower first floor apartment. It is located in Historic Gettysburg, Pa. just 2 blocks to downtown Gettysburg and 4 blocks to Gettysburg College. It is also located within walking distance to Restaurants, Wineries, Museums and Quaint shops and everything else that Gettysburg has to offer. We have everything to make you feel right at home. Early check in and late checkout (if possible) is $25.00 an hour.

Top guest favorite
A modern dining area features a large white table surrounded by upholstered chairs. A vase with fresh flowers sits at the center, and sliding glass doors allow natural light to enter, providing a view of the outdoor space.
Vacation home in Dewey Beach
4.99 out of 5 average rating, 111 reviews

Luxury, Ocean Block 4B/3B Condo at Van Dyke Villas

Come stay at our stunning 4 bedroom, 3 full bathroom, ocean block condo with direct ocean views. This rental has every convenience for the perfect vacation. Located on the same block as the beach, you can have your feet in the warm sand within minutes. Newly renovated, this rental features modern amenities, including a fully upgraded kitchen and bathrooms, a gas fireplace, smart TVs throughout and an amazing, oversized screened-in porch with Ocean views.

Guest favorite
Vacation home in Heathsville
4.98 out of 5 average rating, 95 reviews

Beachfront Getaway on the Chesapeake Bay!

Recharge, reconnect, and reset by staying at our waterfront home. Spend time with your crew while relaxing in this beautiful, well appointed home featuring stunning wide water views of the Chesapeake Bay. "Almost Heaven" is located at the end of a gravel lane, amongst trees, making it the perfect getaway. The expansive patio and beachfront yard offer infinity views of your private beach. Grab a glass, take a sip and put your toes in the sand!

Superhost
Vacation home in Rockville
4.95 out of 5 average rating, 111 reviews

One Bedroom Guest Studio Suite

Come stay at our newly renovated guest suite in the heart of Rockville, MD. The 1-bedroom studio suite is fully furnished with a fully equipped kitchenette and bathroom. Our suite is steps away from public transportation (Route 48) which takes you to the red-line metro (Wheaton or Rockville), and a walkable distance from a shopping center featuring a grocery store, restaurants, etc. There is ample space for parking in front of the property.

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