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

Rachel's BnB
A well outfitted home away from home! A fully stocked kitchen with everything you need to cook for yourselves and your guests. Close to historic downtown Annapolis, the US Naval Academy, St. John's College and MD Statehouse are less than 10 minutes away There are king and queen beds in the rooms, and the 3rd bed is a comfortable pullout couch in the living room. All linens are Egyptian cotton and the beds have real down duvets. Additional cot beds and linens (up to 4) can be provided ($20 each)

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).

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.

Perfect Location by Fed Hill Park 2Bdr/2.5Ba
Our spacious home is waiting for you! You'll love this home's unbeatable & safe location in the heart of Baltimore’s Inner Harbor! Located within walking distance of Federal Hill Park, Convention Center, Orioles & Raven's Stadiums, National Aquarium, Maryland Science Center, M8 Beer, Sagamore Distillery, Fort McHenry, Restaurants/Nightlife/Bars, Farmer’s Market, Shopping, Breweries, Business District, & MARC Train/Metro/Lightrail. Ideal for singles, couples, families, & 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.

Your Hideaway awaits/1-bedroom downtown pad.
There is no place like home when you visit our cozy 1 bed/1 bath abode! This 2nd floor unit is nestled in the rear of a historic home that has been converted into condo living. This space checks all the boxes for a weekend getaway or long-term stay. Enjoy an open living/dinning area, a new memory foam king bed, & a fully furnished bathroom! We offer a keyless entry & 1 parking spot - a rarity for downtown living. Residents live above & below. NO pets, loud music, or parties.

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.

King Bed - Center of Historic District
This cute 1 bedroom apartment is located at the HEART of our lovely town. Steps away from some of the most historic places in the entire United States. Come near the weekend and you can tour our informative museums and wayside exhibits while taking in the local culture. We are a close-knit town and are happy to show out-of-towners "the way". On days we are open enjoy a $15/day credit to our cafe next door. Please enjoy your stay! We are so sorry but no pets allowed.
Popular amenities for rentals with breakfast near Chesapeake Bay
House rentals with breakfast

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Cozy DT Silver Spring Free breakfast and 2 parking

HideawayOasis/VSU/95/FortGreggAdams/FirePT/PoolTBL

Perfect Getaway!

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

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

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

Alice’s DelRay Cottage-Elegant/EV enabled Retreat
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!

Enchanted! 1BR Apt near DCA in quiet neighborhood

Cozy Downtown Suite + Coworking (3S)

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

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

Mulberry in Lewes #2

Comfortable bdrm in 110+ yr old home w/large desk

Quilt Room

Five Red Doors: Historic Hann House

Peaceful Haven

Falling Creek - Rm #4
Other holiday rentals with breakfast

Eye-popping private studio guest suite w/ patio.

Catoctin Comforts, Trails, & Tales

English Basement | Sleep 7 · Park Free + EV Charge

Maple Hollow Farm - A Little Piece of Heaven

Walk to H Street From an Upscale Apartment

Marshfield Guesthouse on river near Williamsburg

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 €26 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 & child-friendly amenities

Pet-friendly holiday rentals
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

Wifi availability
310 of Chesapeake Bay holiday rentals include wifi 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
Destinations to explore
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- Rentals with breakfast United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
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- Chrysler Hall





