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

Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

Quiet Coastal Cottage Escape with Water Views
Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Waterfront Cottage w Private Beach, 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!

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.

The Crab Shack
Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

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.

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach
Fall/Winter promo: Book two nights, get one free on midweek stays (Monday thru Thursday)! Book two nights, get 50% off third night on weekend stays. Send a message after booking, and the promo night will be added. Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) Message for multi-night and monthly rates.

"Bee Haven" Cottage Retreat
Curious about what makes Gloucester so wonderful? Live like a local at "Bee Haven Retreat" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

"Dragonfly" Waterfront Cottage on Chesapeake Bay
Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Peaceful Haven: nature & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

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.
Popular amenities for cottage rentals near Chesapeake Bay
Cottage rentals with a hot tub

Riverside Haven w/ Hot Tub

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Hideaway in the city. Walk 2 harbor, eateries.USNA

Mom's Cottage

Dog friendly *HOT TUB* Close to outlets, Sleeps 7

Bay cottage 🏖on the beach. Stunning views🏝

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
Pet-friendly cottage rentals

Cottage with Modern Updates - Walk to Waterfront!

Hobbs & Rose | A Peaceful Cottage Escape

Creek cottage getaway

A "True" Chesapeake Bay Waterfront Experience!

The Middle Point Cottage at Saint Michaels

Lovely Ocean View Cottage

Cottage on Prentice Creek

Home away from home
Private cottage rentals

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

The Moore Cottage

Charming Waterfront on Chesapeake Bay

White Heron Cottage

A-mazing Beach Cottage on Canal & Trolley Route

Potomac River Freedom Cottage

Cozy Little Cottage

Waterfront Cottage on the Potomac River
Luxury cottage rentals

Villa Positano

Fenced In Backyard, W/Fire pit, Dog Friendly

Beach Front with Paddle Boards and Kayaks

Sanctuary on Sandpiper - Bayfront in Sandbridge

Weems Creek Cottage, Annapolis Waterfront

Waterfront Bay Cottage w/ Your Own Private Beach

Ebb & Flow Beach House - Lewes Bay Beach Retreat

Downtown, walk to everything!
Quick stats about cottage rentals near Chesapeake Bay

Total vacation rentals
Explore 350 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at G$8,352 GYD per night before taxes and fees

Verified guest reviews
Over 28,100 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 170 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wi-Fi availability
340 of Chesapeake Bay vacation rentals include wi-fi 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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