
Holiday rentals with breakfast near Chesapeake Bay
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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.

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!

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.

Designer owned Coastal getaway retreat
Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!

The Heart of Del Ray
Enjoy the best of old and new! Separate apartment in a fully renovated 1920 American Foursquare located in the eclectic Del Ray neighborhood of Alexandria, Virginia, where "Main Street Still Exists." A top-to-bottom renovation provides guests with luxury accommodations in a sparkling clean lower level suite with separate entrance. With free street parking, perfect for business or vacation, guests can easily walk to Mount Vernon Avenue's restaurants, shops, coffee houses, bars and galleries.

Urban 1-Bedrm. Apt. Overlooking Union Square Park
The south-facing, 2nd floor 1-bedroom apartment of an owner-occupied historic townhouse overlooks historic Union Square Park in Baltimore City. Located 2 doors from the author, H.L. Mencken's home place, the neighborhood is primarily residential , but very convenient to the Inner Harbor. The apartment has a full kitchen (with light breakfast items), historic details & eclectic furnishings. Street parking is easy. The space is good for couples and solo adventurers, and business travelers.

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.

"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.

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.

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 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 locked door; separate entrances).

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

Rachel's BnB

Perfect Getaway!

5-BR Home near DC Metro -Free Parking/Full Kitchen

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Entire Guest Suite/Apt in Silver Spring/FDA/NSA

VIBES! *Breakfast*Free Parking*Piano*King Bed*

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

King Bed - Center of Historic District

Just Like Home - Private Entrance Apt in DMV Area

No need to look any further!

Private B&B in Historic Fan

Spacious studio apt, Super location, Parking

Awesome studio tucked away & Centrally located !

Capitol Hill's perfect location! Bright & clean!

Heart of Sykesville! 2 Bedroom Suite! Walk to town
Bed and breakfast rentals with breakfast

Mulberry in Lewes #2

Rustic & Elegant Private Bed & Bath

Cafe on the Bay - breakfast included!

Breakfast, Free Parking & Easy Walk to Mall, Wharf

'Room J' for 1-2 guests in "Black Horse Inn"

The Inn at Dirickson Creek- Room One

Beautiful Historic Home Near Gettysburg

Falling Creek - Rm #2
Other holiday rentals with breakfast

Perfect Location by Fed Hill Park 2Bdr/2.5Ba

Modern Bayfront Escape with Sweeping Water Views

Secluded Waterfront:Kayaks, Sunrises & Unwind

Cozy 1-Bedroom Cottage close to Cape Charles

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

English Basement | Sleep 7 · Park Free + EV Charge

Hidden Gem! 6 Guests • 3 Bed • 2 Baths • Dogs

Walk to Beach, Game Room, Fire Pit, King Beds
Quick stats about holiday rentals with breakfast included near Chesapeake Bay

Total holiday rentals
Explore 310 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 13,580 verified reviews to help you choose

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

Pet-friendly accommodation
Find 90 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
280 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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- Rentals with breakfast United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Nauticus
- Town Point Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall





