
Cottage rentals near Chesapeake Bay
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Top-rated cottage rentals near Chesapeake Bay
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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!

Eastern Shore Romantic Waterfront Getaway Upscale
A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

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.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
The cottage is waterfront and a PERFECT spot for a romantic couples getaway! honeymoon/celebrations Designed with that in mind, it has a hot tub,kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed,a chandelier & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity,a large soaking tub,a tile shower with a soothing 3 function rain shower, is complete with luxury linens, cozy robes & soft towels

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.

"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!

La Casita on Harris Creek, St. Michaels
Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

The Moore Cottage
The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

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.

Waterfront Cottage on the Potomac River
Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.
Popular amenities for cottage rentals near Chesapeake Bay
Cottage rentals with a hot tub

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Riverside Haven w/ Hot Tub

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

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

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Hays Beach House - Hot Tub - Private Beach

902 CH Historic Carriage House + Hot Tub Access
Pet-friendly cottage rentals

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Relaxing Water Views - Mill Creek Cottage

19th Century Coastal Cottage with Modern Amenities

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Creek cottage getaway

"Bee Haven" Cottage Retreat

Rockhold Creek Cottage

Creeks End Farmhouse
Private cottage rentals

The Little Anchor Cottage, St. Michaels, MD

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Charming Waterfront on Chesapeake Bay

Chesapeake Bay Cottage

Little Dipper -private beach,Kayaks & paddleboards

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Beautiful Cottage Waterfront Near Downtown Norfolk
Luxury cottage rentals

Private Beach Access at The OV Beach House

Sanctuary on Sandpiper - Bayfront in Sandbridge

A "True" Chesapeake Bay Waterfront Experience!

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

Sea Salt Cottage: Tranquil Getaway 5 min to beach

A Min. to St.Michaels.Waterfrnt Cottage, Views!

The Good Vibe Cottage

The Potomac House: 13 acre riverfront property
Quick stats about cottage rentals near Chesapeake Bay

Total holiday rentals
Explore 340 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 28,060 verified reviews to help you choose

Family-friendly holiday rentals
270 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wifi availability
330 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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