Vacation home rentals near Chesapeake Bay

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Top-rated vacation home rentals near Chesapeake Bay

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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.

Superhost
A welcoming porch features two Adirondack chairs positioned on a wooden deck. A tall planter filled with purple flowers adds a touch of greenery beside the door, and light shines softly from wall fixtures, enhancing the cottage's entrance.
Vacation home in Lower Township
4.85 out of 5 average rating, 143 reviews

Teal on Teal Ave - Dog Friendly Getaway by the Bay

Kick back and relax in this calm, stylish and tech enabled cottage. Enjoy the fully fenced in yard and close proximity to Cape May’s best breweries and wineries! Your dogs will love the yard, stocked toys and designated pot filler for their water bowl. The kids who will enjoy the fire pit, close proximity to the bay and custom build bunk beds (with a TV in each bunk). Not your average beach cottage - brand new TVs / appliances. Sonos audio and customizable Philips Hue lighting throughout.

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..

Top guest favorite
A view from the balcony features a beach scene with sand dunes and scattered beach umbrellas in the distance. A traffic signal stands at the corner, while a bench and bicycles are visible along the roadside. The sky is clear with a few clouds.
Vacation home in Cape May
4.94 out of 5 average rating, 86 reviews

Best Beach Block in Cape May

Steps to the beach, mall, restaurants. Steps to it all. Please also note: this is a second floor unit above two VERY BUSY businesses (hot dog stand/clothing) Last note:once you park your car, you will have a designated parking spot about 3 blocks away (or you can choose to pay the meter and keep it closer). When we lived here, we parked our cars blocks away. You are on the two most popular streets in town…Jackson and Beach. We lived here for years. It truly is the best location in town.

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
Two red Adirondack chairs are positioned on a wooden dock overlooking calm waters. Lush trees surround the area, providing a serene backdrop. A spacious multi-story home is visible in the background, contributing to a peaceful outdoor setting.
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 kitchen features modern stainless steel appliances, including a gas stove and a spacious fridge. Marble countertops contrast with white cabinetry, and overhead glass cabinets provide storage while allowing visibility of dishes. Natural light floods in from a window above the sink.
Vacation home in Cape May
5 out of 5 average rating, 35 reviews

The Cape May House

Newly renovated 1917 Historical Home nestled by the Marina District on one of Cape May's most iconic tree lined streets. This stand-alone home has just been completed with high end finishes, lots of natural light and colorful, cozy, coastal décor. Enjoy the beach, an abundance of attractions and outdoor activities, or go wine/beer tasting. The home offers a gorgeous chef's kitchen and an outdoor eating area in its spacious backyard that includes an outdoor table and grill.

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
4.96 out of 5 average rating, 103 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.

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!

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