
Holiday rentals with breakfast near Chesapeake Bay
Find and book unique Holiday Accommodation with Breakfast on Airbnb
Top-rated breakfast rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Beautiful and spacious 3 bedroom
Beautifully decorated and spacious home in a charming, Alexandria neighborhood near the King Street metro and the shops and restaurants of Old Town. Just a 16 minute drive to downtown Washington DC, with a chef's kitchen and a relaxing great room. The house is also just a 10 minute drive to the new MGM Casino or the Gaylord Resort and Convention Center at National Harbor. The "no parties in house" rule is strictly followed. If you want to have a party or an event, this is not the place for you.

RetroLux Guest Suite 20 min to Downtown Baltimore
Retro-Lux Suite has the feel of a luxurious separate apartment with all the necessities you may need during your stay; from a warm and cozy bedroom, a clean and airy bathroom, to an inviting bright living room/kitchenette combo well stocked for your needs. The icing on the cake is a fantastic zen-like sunroom to enjoy your morning coffee/tea, or a glass of wine in the evening. Best of all, it's on the first floor, easy to get in and out; you can't go wrong staying at this unique guest suite.

Old Bay Bungalow
This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Annapolis Garden Suite
Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a private ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a deadbolt; no shared indoor spaces; separate entrances).

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🥰

Lil’ House - A Serene Tiny Home Experience
Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

The Forge on Sunnyside Farm
Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

"No Bad Days" in this Fabulous Beachhouse w/ Dock!
You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Eye-popping private studio guest suite w/ patio.
Art filled studio guest suite on quiet wooded lot. Minutes from DC yet feels amazingly private. Enter through charming tiled gate into private patio. Great sleep experience with hypo-allergic organic bedding. Perfect for romantic getaway or base for tourism. Bookshelves stacked with guidebooks and games. Off street parking. South Arlington known for diversity, ethnic restaurants and Amazon HQ2. Close to bus/metro and we comply with AirBnB's COVID-19 cleaning protocol.

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.

Elm Grove Farm Guest Cottage
Our guest cottage is the perfect retreat for a quiet getaway or a quick commute to local historical sites. We are located on a family farm property dating back to the 1880's. Although the old farmhouse is gone our home with attached cottage is filled with decor built by the owner with reclaimed wood from the original home. We are adjacent to Beaverdam Park and located 2 miles from Main Street which boasts the historic Gloucester Courthouse dating back to 1651.

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.
Popular amenities for breakfast rentals near Chesapeake Bay
Holiday House Rentals with breakfast

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Rachel's BnB

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL

Perfect Getaway!

Gorgeous home in lively Chevy Chase/DC location

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

A clean, safe, house full of steel balls and games
Apartment rentals with breakfast

Modern One BR in a Great Location .

THE INN ON CAPITOL HILL

No need to look any further!

Capitol Hill's perfect location! Bright & clean!

King Bed - Center of Historic District

Enchanted! 1BR Apt near DCA in quiet neighborhood

Heart of Sykesville! 2 Bedroom Suite! Walk to town

Historic Church Hill Gracious Apt-Balcony & Garden
Bed and breakfast rentals with breakfast

Breakfast, Free Parking & Easy Walk to Mall, Wharf

Charming bdrm in 110+yr home w/wood fireplace

Military - Active/Retired/Family at Cape Defoe B&B

Private 2BR Cottage with Breakfast - Cedars B&B

Mulberry in Lewes #2

Quilt Room

The Inn at Dirickson Creek- Room Two

Beautiful Historic Home Near Gettysburg
Other holiday rentals with breakfast

Cozy Cottage near the Ocean and Wild Horses

Perfect Location by Fed Hill Park 2Bdr/2.5Ba

Farm House Stay on the Eastern Shore of Maryland

English Basement | Sleep 7 · Park Free + EV Charge

Maple Hollow Farm - A Little Piece of Heaven

Heron's Nest Dover Suite B

Modern Bayfront Escape with Sweeping Water Views

Cozy 1-Bedroom Cottage close to Cape Charles
Quick stats about holiday rentals with breakfast included near Chesapeake Bay

Total holiday rentals
Explore 330 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $51 NZD per night before taxes and fees

Verified guest reviews
Over 14,240 verified reviews to help you choose

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

Pet-friendly accommodation
Find 110 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

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

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

4.7 Average rating
Chesapeake Bay stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with breakfast United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
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