Vacation home rentals near Chesapeake Bay

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Top-rated vacation home rentals near Chesapeake Bay

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Top guest favorite
A cozy living area features a dark gray sectional sofa adorned with bright yellow and patterned throw pillows. A wooden coffee table sits in front, complemented by a sleek remote. The space is brightened by soft overhead lighting and tasteful wall decor.
Vacation home in Arlington
4.98 out of 5 average rating, 164 reviews

1 BDRM Beaut-5 min walk to Metro/10 min from DC

Whether you are traveling for work or pleasure, look no further than this centrally located 1-bedroom/1-bath apartment, just minutes and perfectly located from DC's museums, monuments, & more! This metro accessible, luxuriously decorated apartment can accommodate your every need while in our beautiful city. Travel with ease & take advantage of a fully equipped kitchen, fast WIFI and during downtime, step outside to enjoy a relaxing evening in the shared space under the gazebo with a fire pit!

Guest favorite
A cozy living area features a comfortable gray sofa adorned with patterned cushions, positioned near a stylish coffee table. A colorful area rug lies on the floor, complementing the modern kitchenette equipped with a microwave and stainless-steel appliances. Large windows allow natural light to brighten the space.
Vacation home in Stafford
5 out of 5 average rating, 22 reviews

Stunning one-bedroom private suite

Hi I'm a professional software engineer and a proud father of 3 beautiful children. I'm optimistic, and cheerful, and love communicating with others. Having just started hosting, excited to be a part of this community and to be able to help people feel right at home. Being an explorer myself, I find it really enlightening to discover new places and learn about local cultures. It would be my pleasure to have you as a guest on my new build property and ensure that you have a pleasant stay with me.

Top guest favorite
A charming bungalow is embraced by lush greenery and colorful flowers, featuring a welcoming front porch with seating. A palm tree adds a tropical touch, while the pathway leads to the entrance, inviting guests to explore the comforts within.
Vacation home in Cape Charles
5 out of 5 average rating, 75 reviews

Down By The Bay - Cape Charles -1st Floor Primary

🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 1st floor Primary bed 2026, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June - August

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.

Guest favorite
Four navy blue Adirondack chairs are positioned on the lawn facing the expansive water view of the Chesapeake Bay. The serene outdoor space is framed by trees, offering a peaceful setting to relax while enjoying the scenery.
Vacation home in Heathsville
4.98 out of 5 average rating, 91 reviews

Tranquil Beachfront Getaway on the Chesapeake Bay!

Recharge your battery and reset your mind by staying at our waterfront paradise. Spend time with your tribe 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. Bait a crab pot to catch your own dinner or enjoy a meal from one of the local restaurants.

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, 45 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, 252 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
A charming waterfront home is set amidst lush greenery, featuring a welcoming porch and a two-car garage. Vibrant foliage surrounds the property, while soft sunlight filters through the trees, highlighting the serene landscape.
Vacation home in Severna Park
5 out of 5 average rating, 42 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!

Superhost
The farmhouse features a light blue exterior with white trim, complemented by a prominent gabled roof. A front porch, supported by decorative columns, offers seating, while the surrounding yard is lush with grass and various shrubs, creating a spacious and welcoming entrance.
Vacation home in Onley
4.89 out of 5 average rating, 62 reviews

Stylish Farmhouse - porch, firepit

Beautiful rural farmhouse with stylish decor and a lovely front porch overlooking a serene field. This homey space is chic and elegant with a modern kitchen, bath and amenities. Step outside for a 2 mile wooded walk/bike ride to a tiny secluded BEACH. Watch the stars from the front porch, grill outside, fire pit, or chill out with ROKU tv. Modern plus old-fashioned gives you a nostalgic, stylish, and comfortable rural getaway. Great central base for exploring the entire Shore!

Guest favorite
The living room area features a comfortable gray couch complemented by decorative pillows. A glass coffee table sits in front, accompanied by a green floral chair and an upholstered footstool. The space is well-lit, showcasing an open design that connects to the dining area.
Vacation home in Takoma Park
4.91 out of 5 average rating, 67 reviews

Spacious Garden Apartment on Delightful Street

This delightful apartment is on the ground floor of a large single family house in a charming neighborhood, just 2 blocks from the center of Takoma Park, a 15 minute walk to the Metro. With its open floor plan, you will enjoy the large living room and windowed alcove, a fully-equipped kitchen, dining room and ample-sized bedroom with wall-to-wall closets. There is a separate entrance and laundry room. The house has a large front yard, with shade trees and nice gardens.

Superhost
A vibrant sunset casts a warm glow over the water, with rich hues of orange, pink, and purple reflected in the calm surface. A dock extends into the scene, framed by grassy edges, contributing to the serene atmosphere along the river.
Vacation home in Gloucester County
4.8 out of 5 average rating, 56 reviews

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

Superhost
A comfortable bedroom features a spacious bed with floral bedding, complemented by three framed botanical prints on the wall. A cozy chair is positioned next to the bed, and a light rug creates a soft contrast against the wood-like flooring.
Vacation home in Rockville
4.95 out of 5 average rating, 110 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.

Popular amenities for vacation home rentals near Chesapeake Bay

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