
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.

Gettin to the point. ( Cove Point Beach)
Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

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.

"Bee-Z Haven" Waterfront Cottage on the Ware River
Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

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.

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

Waterfront Cottage w Hot Tub, Kayak, Fishing
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, take a dip in the hot tub, 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!

The Laughing King Retreat Honeymoon Island Cottage
Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Tiny House Treasure on the Rappahannock River
The Riverbunk is located on the Rappahannock River in Colonial Beach, Virginia. The scenic River is home to Eagles, ospreys and great blue herons. The river offers the perfect kayaking experience and for boaters, a boat launch is within walking distance. Fishing, hunting, hiking and sightseeing are popular in this area. We are 420-friendly where smoking is allowed outside. The rural area is perfect for quiet downtime and fun activities.

Rumbley Cottage on the Tangier Sound-Private Beach
Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Beach Home | King Bds | Firepit | Backyard Dining
Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

Dinna Fash-3 BR Waterfront Log Cabin
Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.
Popular amenities for beachfront rentals near Chesapeake Bay
Pet-friendly beachfront home rentals

The Crab House - a Private, Waterfront Guest House

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

A "True" Chesapeake Bay Waterfront Experience!

Historic St. Mary's City, MD

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Charming Waterfront Home with Expansive Views

Beach Please! River cottage w/private beach & dock

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
Beachfront home rentals with a pool

Positano Villa

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

IslandCoveParadise:LuxNewlyBuilt-Brdwk pool/2CarGg

Oceanfront Gem VaB Studio Exceptional Views

Chesapeake Bay View 3BR/2BA Duplex

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool

The Barn at Pond Point - Riverfront Home

Chester Riverfront At Kent Narrows
Private beachfront home rentals

Osprey's roost: Spring and summer 2025

Cozy beach side condo

Cove Point Lighthouse Keeper's House- Side B

Little Dipper -private beach,Kayaks & paddleboards

Cape St Claire waterfront getaway "The Apartment"

Country House on the Bay

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

Sea Dreamer
Luxury beachfront home rentals

Steps to Chic’s Beach! Sleep for 12 with Garage

Red Point Lighthouse

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Beach Front with Paddle Boards and Kayaks

Waterfront Cabin on the Chesapeake

Potomac Waterfront Home and Estate

Waterfront with sweeping bay view & private beach

Coastal Farmhouse Getaway
Quick stats about beachfront rentals near Chesapeake Bay

Total vacation rentals
Explore 500 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 34,760 verified reviews to help you choose

Family-friendly vacation rentals
380 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 240 rentals that welcome pets

Vacation rentals with a pool
70 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
500 of Chesapeake Bay vacation 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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- Beachfront rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Cape Charles Beachfront
- Norfolk Botanical Garden
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