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

Little Red House on a Farm - Quiet Rural Waterview
The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

Guesthouse at Vessel Farm & Winery, Waterfront
Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

The Little House on the Farm, Water Access
Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

Sunset Breezes - quiet waterfront retreat
Enjoy our waterfront home styled after historic bay lighthouses. Relax by the water in a hammock under the tall pines. Gather with family and friends around the fire pit. Take in the beautiful water sights while paddling in a kayak, canoe, or paddleboard. Laugh with family and friends while playing corn hole, croquet, or bocce ball waterside. Photograph abundant wildlife - bald eagles, blue herons, osprey, deer, turkey and numerous waterfowl. Dine on the deck while enjoying beautiful sunsets.

Private romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

19th Century Coastal Cottage with Modern Amenities
Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Waterfront Farmhouse Meets Modern Luxury
Enjoy all that the Eastern Shore has to offer while staying at the neoclassical 19th-century "Osprey's Reach" farmhouse. Osprey's Reach blends the original character of Kent Island with modern comforts of a full house restoration, all while enjoying stunning sunsets over the Chesapeake, from the private dock or poolside. Kent Island is centrally located for short day trips to Annapolis, Easton, St. Michael's or Chestertown, with family-friendly dining and shopping options on-island.

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.

Waterfront Getaway with Dock
Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

La Casita on Harris Creek, St. Michaels
Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Peaceful Haven: nature & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.
Popular amenities for farmstay rentals near Chesapeake Bay
Family-friendly farm stay rentals

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Farm Stay - Guest Suite w/ Private Entrance

-Scenic Historic Charm- Spruce Edge Guest House

Bell Farm Cottage LLC - quiet and peaceful

Dorothy's Chesapeake Delight

Beach Highway Hobby Farm

Fall foliage, Alpaca Views + Hot Tub Getaway

Lovely space above barn on a working farm!
Farm stay rentals with a patio

Lg 2bd/1ba | Chef's Kitch | Peaceful Parklike Yard

Outrange at Blue Heron Farm

Pyle Cottage, circa 1750

Creek front home *heated pool open year round!*

Spruce Run Cottage, Farm stay on Catoctin Mountain

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Cozy Barn Loft: Country Views & Central to Beaches

Historic Farmhouse. Peace & Quiet on 5 acres
Farmstay rentals with a washer and dryer

Cozy Riverside Cottage in the Woods

Historic St. Mary's City, MD

"Queen Bee “ WATERVIEW & WALK TO ACCESS the River

The Rosé Retreat: Kayaks-Screened Porch-RELAX

Cozy Waterfront Apartment Chester, MD

Watch Deer from a Farm Cottage

The Williamsburg Retreat Gorgeous Private Acreage

Bohemia Vista CC Horse Farm Apartment
Other farmstay vacation rentals

Waterfront Modern Guest Barn

Waterfront Cabin on the Chesapeake

Private Country Beach Retreat

Barn Apt on Tranquil Historic Farm--Amazing Views

Creekside Forest Nature Retreat : Mongolian Yurt

1765 Log Home in a Peaceful Setting

The Cock and Feather Guesthouse

3 BR Cottage on Mallardee Farm in Williamsburg
Quick stats about farmstay rentals near Chesapeake Bay
Total rentals
60 properties
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
Total number of reviews
4.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 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 fire pit Chesapeake Bay
- Rentals with a washer and dryer Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Beach condo 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
- Apartment 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
- RV 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 home theater 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
- Condo rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Farmstay 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