
Guest house holiday rentals near Chesapeake Bay
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Moody Modern Cottage Hot Tub-Fire Pit-Creek views
Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Waterfront Guesthouse II on the Rappahannock
The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Calico Cottage Guest House, king bed, free parking
Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Nautical Charm and relaxing waterview!
Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchenette (limited-no range), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Rosses Chance Guest House
This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Cozy Retreat w/Private Beach Access
Welcome to our charming Annapolis retreat! Nestled in a quiet community on the Chesapeake bay, Barefoot Cottage offers a perfect blend of comfort and convenience. Enjoy a stroll around iconic landmarks, savor local cuisine, or unwind with a walk on the beach. Thoughtfully interiors and modern amenities, our Airbnb promises a memorable stay for your solo trip, romantic getaway, sailing enthusiasts or USNA visitor. Book now for an unforgettable experience in this historic maritime city!

Chill in The Crib! Easton, Maryland
Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Urban Cottage,MD minutes from DC/National Harbor
Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Little House by the water
Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Cute cottage studio with full kitchen and laundry
Warm and inviting private upstairs studio with off-street parking, full kitchen, laundry, electronic fireplace, rainhead shower and deck with tranquil garden in the Riderwood area of Towson. Studio is situated next to owner's stone cottage, and is tucked away at the back of 2.5 acres with private bridge and creek. Centrally located to shops, galleries, walking and biking trails, Lake Roland, Baltimore, DC and PA. Especially suitable for a restorative or romantic getaway.

Waterfront Getaway - View of bay from your bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Studio on the Bay.
This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.
Popular amenities for guest house rentals near Chesapeake Bay
Family-friendly guest house rentals

Cozy Private Cottage Near The Beach

Charming Yorktown Battlefield Cottage

Gorgeous Two-Story Guesthouse w/ Driveway & W/D

Fox Cottage *Pet Friendly*

Cozy Beach Cottage

1 large room efficiency in detached garage.

Spacious nature retreat close to city | The Bohive

Private Sunny Cottage with King Bed + Yard / Patio
Guest house rentals with a patio

Casita Del Ray — Alexandria Studio Apartment

BlueBird Nest

Private Country Guesthouse Getaway Minutes from UD

Charming Carriage House in the heart of the Fan.

DC Treehouse - Charming, private 1-bdrm ADU in DC

The Guest Suite

Sunny Guesthouse steps from Towson!

"Lofty Cottage" Adorable 1-Bedroom Guest House
Guest house rentals with a washing machine and dryer

Carriage House near Navy Stadium, parking, pets

"L'auberge du Cape Saint Claire"

Adorable Large Efficiency Getaway Retreat

Spacious Guest House 10-15 min to DC

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

Capitol Hill Carriage House

Garden View, a spacious 1 bedroom with loft.

Sun Sea and Sand
Other guest house holiday rentals

Cozy Guest House Near Park

Garden Cottage

NEWLY Renovated -- Waterfront Getaway

Patuxent River View

The Book Nook - A Private Downtown Retreat

Blue Crab Bungalow

The Garden Studio

Poolside Paradise in Monrovia, Maryland.
Quick stats about guest house rentals near Chesapeake Bay
Total rentals
150 properties
Nightly prices starting at
$52 SGD before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Rentals with an EV charger Chesapeake Bay
- Rentals with a firepit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Hotel rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Villa rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Flat rentals Chesapeake Bay
- Boutique hotel rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Loft rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a cinema Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Guest house rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Haven Beach
- Assateague Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Piney Point Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club
- Little Creek Beach
- Wallops Beach