Private suite holiday rentals near Chesapeake Bay

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Top-rated private suite rentals near Chesapeake Bay

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

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Top guest favourite
A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.
Guest suite in Chestertown
4.99 out of 5 average rating, 242 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Top guest favourite
Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.
Guest suite in Lusby
4.98 out of 5 average rating, 367 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Top guest favourite
A scenic view of the Rappahannock River reveals a wide pathway lined with paving stones leading towards a wooden dock. Lush green grass frames the waterfront, complemented by flowering plants in a decorative pot. The sky above is partly cloudy, enhancing the tranquil setting.
Guest suite in Dunnsville
5 out of 5 average rating, 286 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Guest favourite
The living and dining area features a white sofa facing a mounted television. Two round chairs and a circular table with teal chairs create a dining space. Light-colored tiles extend across the floor, complemented by a decorative area rug. Three images of tranquil waters are hung on the wall.
Guest suite in Washington
4.86 out of 5 average rating, 153 reviews

Convenient, private basement apt near downtown DC

Keep it simple at this private English basement apartment. In-unit washer/dryer, full kitchen, spacious living/dining area. Walking distance to Medstar, Children's National, & VA Hospitals; Catholic, Howard & Trinity Universities. city bus stop 1 block away; metro train (red & green lines) 1 mile away. Less than 5 miles to Union Station, Capitol, White House, & National Mall. We live upstairs with an excitable dog & active toddler. Please book expecting modest city & neighbor noise =)

Guest favourite
A studio apartment is displayed, featuring a spacious bed and a blue sofa. Modern furnishings include a light-colored dining table with two chairs. A framed black-and-white photograph adorns the wall, complementing the neutral tones of the decor. Soft lighting brightens the warm ambiance.
Guest suite in Bowie
4.94 out of 5 average rating, 103 reviews

Modern studio near UMD hospital

Stylish studio basement apartment located 3 minutes from UM Capital Region hospital. As you pull up to our quiet neighborhood you can park right in the drive. The entrance is around the corner to enter your private space. We offer all the essentials needed to have a relaxing stay. The full service kitchen is well equipped and inviting. A large over sized sink for a quick clean up. Come unwind after a long day in this private studio with rainshower and jets. Long stays are welcome.

Top guest favourite
Guest suite in Annapolis
4.95 out of 5 average rating, 118 reviews

Annapolis Garden Suite

Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Top guest favourite
A spacious room features a king-sized bed framed by framed photographs. A wooden chair sits beside a small table with a plant. Sliding glass doors open to a private balcony, allowing natural light to fill the space.
Guest suite in Peach Bottom
5 out of 5 average rating, 166 reviews

Conowingo Creek Casual

Kick back and relax in this handicap accessible, clean and stylish country charm efficiency apartment, complete with two outdoor seating spaces, walking paths and beautiful scenery located in rural southern Lancaster County. The area is surrounded by country and Amish charm, with nearby hiking trails, while a 30 minute drive will have you in downtown historic Lancaster City where you can stroll, shop and on Tuesday, Friday and Saturday visit the historic Central Market.

Top guest favourite
The spacious studio features a white, wooden bed with dark blue bedding, complemented by a bedside table and lamp. A kitchenette is visible, along with a dining area set for two. Light pours in through sliding glass doors, leading to a small outdoor area.
Guest suite in Fredericksburg
4.99 out of 5 average rating, 338 reviews

Spacious studio apartment - The Inn at Dewberry

The Inn at Dewberry. Our roomy studio apartment is located in a quiet friendly neighborhood just 4 miles from downtown historic Fredericksburg. For traveling medical personnel, Mary Washington Hospital is less than 4 miles away. Our area is rich in Civil War history with lots of great places to dine, shop, or catch a Fredericksburg National game at the ballpark. Close to I95 for a trip to Washington, DC (60 mi) or south to Richmond. Kitchenette but no stove. Microwave.

Superhost
The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.
Guest suite in Crisfield
4.77 out of 5 average rating, 244 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Top guest favourite
Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.
Guest suite in Norfolk
4.93 out of 5 average rating, 627 reviews

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay.

Guest favourite
Guest suite in Arnold
4.94 out of 5 average rating, 202 reviews

Coastal Comfort Suite Near Annapolis, Hottub, EV

Our pool and hot tub are closed for the season. Ideal for a couple's retreat, this king suite guest room has a seating area, mounted TV, and coffee bar, microwave, and mini-fridge. An ensuite bathroom provides a luxurious shower and a spacious closet. The pool and hot tub are seasonal. Please don’t hesitate to reach out with any questions, concerns, or expectations so that we can address them prior to your stay.

Guest favourite
The sleeping area features two queen beds, one with a wooden headboard and layered bedding. A small table is positioned nearby. Decorative wall art and a patterned area rug add visual interest to the hardwood floor, complemented by recessed lighting in the ceiling.
Guest suite in Lusby
4.84 out of 5 average rating, 166 reviews

New Light suite, appartment comfortable living

Guest Suite apartment , on the ground floor. located on the back side of the house. The apartment includes 2 queen beds, 50 inch TV, kitchenette, living room dining area, and full bath. This apartment is fully private with a private entrance on the backside of the house. (no shared spaces). Please include total number of guests.

Popular amenities for private suite rentals near Chesapeake Bay

Quick stats about private suite rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 150 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 17,180 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    150 of Chesapeake Bay holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.9 Average rating

    Chesapeake Bay stays are highly rated by guests – averaging 4.9 out of 5!

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