
Beachfront rentals near Chesapeake Bay
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Top-rated beachfront rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Waterfront Cottage w Water Access, Sauna, Hot Tub
Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, relax in our hot tub, sweat in the sauna, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

Waterfront with sweeping bay view & private beach
Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Osprey's roost: Spring and summer 2026
Hidden treasure! Come join the osprey along the Potomac River in the Northern Neck of Virginia! This 4 bedroom/3 bath custom home is at the end of a quiet lane and sits on a point of land between the Potomac River and Blackbeard’s Pond, making for magnificent river views from sunrise to sunset. Enjoy swimming, canoeing, Bocce on the lawn, barbecue on the deck! Osprey’s Roost is the perfect retreat to rest and recharge, ideal for a romantic week away, a girls’ weekend or a family gathering!

Waterfront Guesthouse II on the Rappahannock
The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

A "True" Chesapeake Bay Waterfront Experience!
Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!

Beach Front and 'Perfectly Placed'
Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Waterfront Home on the Chesapeake Bay-Pvt Beach
A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Osprey's Retreat Waterfront w/ private beach/dock
Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage
Popular amenities for beachfront rentals near Chesapeake Bay
Pet-friendly beachfront home rentals

The Laughing King Retreat Honeymoon Island Cottage

Charming Waterfront Home with Expansive Views

Huge 4 BR Beach House | Fire Pit | Fenced Yard

The Crab House - a Private, Waterfront Guest House

Stunning Beachfront Cottage on the Chesapeake

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

The Little Gypsy BoHome

Red Point Lighthouse
Beachfront home rentals with a pool

Chester Riverfront At Kent Narrows

Villa Positano

Private Pool at the Oceanfront in a Spacious Home

Mid century vacation condo newly renovated.

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

OceanfrontJewel|DirectOceanView•NewlyRenovatedPool

Oceanfront Condo with Spectacular Beach View

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Private beachfront home rentals

Waterfront Cabin: beach, kayaks, hot tub & firepit

Chesapeake Bay Retreat | Private Dock + Beach

Private beach retreat in historic St. Mary's City

"The Little Red Cabin" aka The Galley

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

Private Beach Front w/ Dock Colonial Beach Water

Charming Historic 2 Bedrooms on the Chesapeake Bay

Cove Point Lighthouse Keeper's House
Luxury beachfront home rentals

Sunrise Waterfront Potomac Beach Haus

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

Potomac Waterfront Home and Estate

Beachfront stay with kayaks & paddleboards

Chic’s Beach Oceanfront 3BR Home With Deck Views

Beachfront Home with Unobstructed Water Views

Stylish Beach House, Hot Tub, Pet Friendly

Long Beach Wellness Retreat Hot tub/Sauna/Plunge
Quick stats about beachfront rentals near Chesapeake Bay

Total holiday rentals
Explore 510 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $50 NZD per night before taxes and fees

Verified guest reviews
Over 35,160 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 230 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
500 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.8 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!
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