
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.

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!

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.

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🥰

"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.

Annapolis Garden Suite
Welcome! We’re tucked away on a forested residential street, roughly a 7 minute drive from restaurants, coffee shops and all that Annapolis has to offer. 15m from the coast, 30m from Baltimore and 35m from DC. Tl;dr: this is a private ground-level guest suite with 3 beds, 2 bedrooms, 1 desk (optional standing desk), 1 kitchen with oven, dishwasher + Nespresso/pour over, 2 tvs, laundry room with washer/dryer, fast wifi, a pool, patio and a forest view. We live on the top floor.

Modern 3-Level Stay| Hot Tub | Game Room | Parking
Spacious 5BR home near D.C. with hot tub, fire pit, and game room—perfect for families or groups! Enjoy 3 levels of comfort, a full kitchen, fast Wi-Fi, smart TV, and self check-in. Relax in the private backyard, grill out, or unwind in the hot tub. Pet-friendly and sleeps 12 comfortably. Located in a quiet neighborhood just minutes from downtown Silver Spring and Washington, D.C. Free parking, kid-friendly, and ideal for work trips or weekend getaways. Book your stay today!

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.

Walk to Georgetown - Glover Park Guest Suite
Covid-19 safe and separate entrance suite, with no shared utilities (radiator in winter and wall unit AC in summer). The space is bright and has windows facing East and South. The apartment has direct access to a private patio, where you can relax with a cup of coffee in the morning sun. The general atmosphere is cozy yet it has a contemporary feel thanks to its bamboo floors in the bedroom and modern tiles in the bathroom and kitchen. No smoking is allowed in the unit.

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.

Serene Flat at U/14th St in Shaw on Quaint Swann
Luxurious, private and comfortable retreat in the heart of the most bustling part of DC in the U Street/14 Street corridor. Steps to the best of city living, while on one of the most beautiful, quiet streets in DC, enjoy this award winning, sunny 1 BR penthouse flat. As architects, we've designed beautiful spaces in DC, so expect gorgeous finishes and thoughtful touches throughout. Beautiful modern renovation to historic brick walled home.
Popular amenities for rentals with breakfast near Chesapeake Bay
House rentals with breakfast

Ghent on the Corner: Cozy 3 bed 2.5 bath home

Perfect Getaway!

Gorgeous home in lively Chevy Chase/DC location

Luxury 4 Bedroom - Pool/HotTub/Fire Pit

Modern Bayfront Escape with Sweeping Water Views

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

RetroLux Guest Suite 20 min to Downtown Baltimore

Alice’s DelRay Cottage-Elegant/EV enabled Retreat
Apartment rentals with breakfast

Modern One BR in a Great Location .

THE INN ON CAPITOL HILL

Perfect DC stay with parking! Sanitized 100%

Capitol Hill's perfect location! Bright & clean!

King Bed - Center of Historic District

Enchanted! 1BR Apt near DCA in quiet neighborhood

Spacious studio apt, Super location, Parking

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

Breakfast, Free Parking & Easy Walk to Mall, Wharf

Cozy private room in Annapolis home

Suburban Sanctuary

Private 2BR Cottage with Breakfast - Cedars B&B

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

Quilt Room

Mulberry in Lewes

Cafe on the Bay 2- breakfast included!
Other holiday rentals with breakfast

Gorgeous Designed 2-bedroom in DC, with parking!

Eye-popping private studio guest suite w/ patio.

Piankatank Riverfront Perch B, Mathews VA

No need to look any further!

Trust-n-travel

The Perfect View Virginia Tiny Home

Elegant Garden Suite | Walk to Union Market/Metro

Maple Hollow Farm - A Little Piece of Heaven
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 € 25 per night before taxes and fees

Verified guest reviews
Over 14,230 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
300 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
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- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
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