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Farmstay holiday rentals near Chesapeake Bay

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Top-rated farmstay rentals near Chesapeake Bay

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Top Guest favourite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

La Casita on Harris Creek is an architecturally unique guest house situated on a private 40-acre farm in the heart of the Chesapeake Bay, 5 min by car to Saint Michaels, MD. The guesthouse, adjacent to the owner's main farm house, features an upstairs loft, open plan first floor TV/WiFi, full bath/shower, galley kitchen/ cook top stove, microwave, stainless refrigerator, microwave, stainless refrigerator. An adjacent private pool is available for guests. TALBOT COUNTY LICENSE NUMBER STRN 26-39

4.98 out of 5 average rating, 204 reviews
Guest favourite
Tiny home in Accomac

Little Red House on a Rural Farm for Stargazing

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. • Pets are welcome • Escape the noise, reset in nature • Epic stargazing • Peaceful sleep • Thoughtful interior design • Large full bath • Comfy patio for coffee, wine, reading • Firepit with wood onsite • Large private outdoor shower in woods • Wide open spaces • Fast WIFI • Superhost 13+ years

4.94 out of 5 average rating, 542 reviews
Top Guest favourite
The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.
Farm stay in Cape Charles

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.

5.0 out of 5 average rating, 435 reviews
Guest favourite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross

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

Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

4.93 out of 5 average rating, 130 reviews
Top Guest favourite
Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

4.99 out of 5 average rating, 134 reviews
Top Guest favourite
The Airstream is surrounded by tall trees, with a spacious deck featuring comfortable seating arrangements. Oversized Adirondack chairs and a large sofa face the natural scenery. Soft lighting adds warmth, enhancing the outdoor experience in a peaceful, wooded setting.
Farm stay in Cape Charles

Ultimate Airstream Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning Airstream retreat 10 mins from Cape Charles. The 1969 Airstream has been converted into a contemporary studio with all the comforts of a luxury hotel room. Wake up to the birds singing in the trees that completely surround the huge deck. Take a walk on our trails. Enjoy watching the animals. Feed the Alpacas. Take a trip into Cape Charles for restaurants and shopping, then enjoy a movie in the Airstream at night.

4.97 out of 5 average rating, 312 reviews
Top Guest favourite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock

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!

4.99 out of 5 average rating, 350 reviews
Top Guest favourite
The image displays The Tiny Red Barn, featuring white rocking chairs on a welcoming porch. Lush green grass surrounds the entrance, while trees create a serene woodland backdrop. To the right, a wooden dock extends into the calm waters of the Diascund Reservoir, with an American flag gently waving.
Farm stay in Lanexa

Tiny Red Barn on The Reservoir-Near Williamsburg

Important: NO 3RD PARTY RES. Tiny Red Barn is a labor of love built by us for you on the Diascund Reservoir with water views, wooded trails and sunsets. We feel like we're on vacation every day of the year and look forward to sharing our 26 acres with you. Heavily wooded land with rolling trails, birds, deer, squirrels, turtles, chickens, mini donkeys and bees. A large amount of our property sits on the Diascund Reservoir which provides a whole other side of nature. Opened April 1, 2021.

5.0 out of 5 average rating, 113 reviews
Top Guest favourite
The exterior of a two-story wooden structure is presented, featuring a staircase leading to a covered balcony. The building is surrounded by trees displaying fall foliage, creating a serene outdoor atmosphere. A gravel area is noted at the base, with a vibrant red and white camper positioned nearby.
Apartment in Greenwood

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

4.97 out of 5 average rating, 701 reviews
Top Guest favourite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

4.97 out of 5 average rating, 626 reviews
Top Guest favourite
Home in Deale

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

4.98 out of 5 average rating, 155 reviews
Top Guest favourite
A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.
Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

Heartsong Farmhouse was completely renovated in 2019. Beautiful hardwood floors, brand new furniture, in a modern farmhouse style with a Boho vibe. The entire home is filled with beautiful natural light and the brick walls ensure a peaceful nights sleep. The yard is completely surrounded by a 15ft hedgerow of holly, magnolia and camellias, like walking into a secret garden. You will feel welcome from the moment you drive up. The Farmhouse is also beautifully decorated for the holidays.

4.98 out of 5 average rating, 310 reviews

Popular amenities for farmstay rentals near Chesapeake Bay

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-Friendly farm stay rentals

Top Guest favourite
The exterior of a large black barn is shown under a clear blue sky. Two wooden doors are open, revealing a welcoming entrance. Flower pots are arranged along the path, while two wooden chairs are positioned in front, inviting relaxation amidst a tranquil rural setting.
Farm stay in Charles City

Lovely space above barn on a working farm!

4.99 out of 5 average rating, 162 reviews
Guest favourite
Farm stay in Heathsville

Fleets Cove Farm *PETS STAY FREE*

4.98 out of 5 average rating, 123 reviews
Top Guest favourite
A cozy cottage stands amidst lush green trees, showcasing a welcoming front porch with a circular doormat. Large windows allow natural light to filter in, complemented by the inviting wooden door, creating a harmonious blend with the surrounding forest.
Tiny home in West Point

The Cozy Cottage At Grateful Meadows

4.96 out of 5 average rating, 299 reviews
Guest favourite
An attic bedroom features two spacious beds, each adorned with warm-toned pillows and throws. Bright overhead lights accentuate the light-colored walls and wooden floor, while a decorative area rug adds texture. A window provides natural light, enhancing the peaceful atmosphere.
Home in Salisbury

1900's Modern Farmhouse on 7.5 private acres

4.93 out of 5 average rating, 141 reviews
Top Guest favourite
A rustic outdoor scene features several alpacas grazing and exploring a spacious area. A weathered barn is visible in the background, surrounded by trees and open land. A black water trough is placed nearby, reflecting the clear blue sky with scattered white clouds.
Farm stay in Bel Air

Watch Deer from a Farm Cottage

4.98 out of 5 average rating, 201 reviews
Top Guest favourite
A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.
Farm stay in Princess Anne

Farmhouse located on a horse farm

4.95 out of 5 average rating, 124 reviews
Guest favourite
A charming 1930's farmhouse is framed by lush greenery and a spacious lawn. The exterior is enhanced by a welcoming front porch and surrounded by mature trees, providing a serene rural setting. A gravel path leads to the house, indicating easy access.
Home in Park Hall

Rolling Stone Farmhouse 2m Historic St. Marys City

4.93 out of 5 average rating, 136 reviews
Guest favourite
An airy living area features a large curved sectional sofa on a textured rug, complemented by two elegant lamps. Floor-to-ceiling windows provide ample natural light, and a tall stone fireplace is accentuated by wood detailing. The open layout includes a glimpse of the kitchen in the background.
Cabin in Greenwich

The Hepburn-Hot Tub & Fire Pit

4.93 out of 5 average rating, 268 reviews

Farm-stay accommodation with a patio

Top Guest favourite
A serene outdoor view showcases a blue cottage with large windows and a covered deck. Bright orange daylilies bloom in the foreground, complementing the lush greenery surrounding the property.
Guest suite in Machipongo

Peaceful Suite in Machipongo

5.0 out of 5 average rating, 154 reviews
Guest favourite
The exterior of a two-story cottage is shown, featuring a blue metal roof and white siding. Blue shutters frame the windows. A small deck is visible in front, furnished with two adirondack chairs in bright green. A door centrally accesses the home.
Cottage in Wingate

Blue Crab Cottage: Remote+Nature+Fishing+Views

4.84 out of 5 average rating, 102 reviews
Top Guest favourite
A welcoming space is featured, showcasing a luxurious jacuzzi with a wooden tray holding candles and decor. Nearby, a cozy living area with a modern couch is highlighted against an artistic forest mural. An adorable Highland cow stands nearby, adding a touch of rustic charm.
Farm in Selbyville

Sleep in a One-of-a-Kind Barn near Ocean City Mary

4.98 out of 5 average rating, 320 reviews
Top Guest favourite
The custom-built home features a blend of stone and siding, set within a grassy landscape. A covered front porch invites relaxation, while large windows allow ample natural light. Solar panels are visible on the roof, integrating sustainable energy solutions.
Farm stay in Centreville

3 bedroom home with pool and game room

4.93 out of 5 average rating, 131 reviews
Top Guest favourite
Aerial view of a spacious cottage surrounded by lush green pastures and woodlands. The property features a large, circular driveway and open lawn areas, with fields stretching into the distance. The landscape showcases a blend of farmland and natural surroundings.
Farm stay in Damascus

Large countryside escape

5.0 out of 5 average rating, 127 reviews
Top Guest favourite
The exterior of the cabin displays a rustic design with wooden accents and large windows that invite natural light. A spacious grassy area surrounds the structure, complemented by trees and landscaping. A small patio area is visible, offering a place to sit outdoors.
Farm stay in Chestertown

Outrange at Blue Heron Farm

4.96 out of 5 average rating, 164 reviews
Guest favourite
A comfortable living area features a cozy gray sofa facing a stone fireplace. A wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Light enters through a nearby window, illuminating the space.
Guesthouse in Dover

Country Guest House

4.84 out of 5 average rating, 212 reviews
Guest favourite
The farmhouse exterior is showcased, featuring a white façade with brown shutters. A wide path leads to the front entrance, framed by landscaped gardens and a spacious lawn. The metal roof and symmetrical design contribute to the country charm against a backdrop of blue sky and fluffy clouds.
Farm stay in Thurmont

Private Farmhouse Escape w/ Mountain Views

4.96 out of 5 average rating, 169 reviews

Farmstay rentals with a washing machine and dryer

Top Guest favourite
A serene cottage, surrounded by lush greenery, features a welcoming front porch with chairs and warm lighting. A gravel pathway leads to the entrance, highlighting the harmony between the home and its natural surroundings.
Farm stay in Smithfield

Cozy Farm Cottage with Horses, Fire Pit, & Trails

5.0 out of 5 average rating, 194 reviews
Top Guest favourite
An aerial view showcases the expansive riverfront property surrounded by lush green fields and waterways. The deep Cohansey River meanders through the landscape, reflecting the sky. Various shades of green and water create a tranquil and serene environment.
Home in Bridgeton

THE SORA with Disco, Hot Tub & Pool

4.99 out of 5 average rating, 285 reviews
Top Guest favourite
A single-story cottage is surrounded by lush greenery and vibrant flower beds. A wooden deck extends around the front, providing access to the home. The well-maintained lawn features a variety of plants and shrubs, enhancing the inviting outdoor space.
Cottage in North East

Persimmon Pastures

4.97 out of 5 average rating, 715 reviews
Top Guest favourite
Home in Milton

BeachHaven: STEPS TO SAND, Pet-Friendly, +Linens

4.99 out of 5 average rating, 121 reviews
Guest favourite
The side view of a historic brick house is shown, featuring a gabled roof with multiple chimneys. The whitewashed brick exterior contrasts with the green trim around the windows and door. The well-maintained lawn surrounds the structure, complemented by mature trees in the background.
Guesthouse in Stevensville

Circa 1700 Chesapeake Colonial Home

4.92 out of 5 average rating, 197 reviews
Top Guest favourite
The interior features a festive living area with a reflective mirror and decorated Christmas tree, accompanied by a cozy fireplace. An outdoor deck showcases inviting seating areas and a porch swing, while a hot tub offers relaxation. Three friendly alpacas graze nearby, adding to the rustic charm.
Place to stay in Nokesville

Fall foliage, Alpaca Views + Hot Tub Getaway

4.98 out of 5 average rating, 367 reviews
Top Guest favourite
A lush field is filled with blooming yellow flowers under a clear blue sky. In the background, a red barn is situated near a fence, surrounded by trees that provide a natural border to the landscape.
Farm stay in Williamsburg

3 BR Cottage on Mallardee Farm in Williamsburg

4.97 out of 5 average rating, 419 reviews
Top Guest favourite
A charming white farmhouse is set against a backdrop of rolling hills, with a vibrant row of sunflowers blooming in the foreground. The open pasture offers a serene landscape, enhanced by the warm light of the setting sun casting a gentle glow.
Farm stay in Mount Airy

Sunsets from a Haven on a Hill

4.98 out of 5 average rating, 110 reviews

Other farmstay holiday rentals

Top Guest favourite
The interior of the cottage features rustic wooden beams and stone walls, creating a charming ambiance. A staircase leads to a lofted area. An inviting dining table sits at the center, surrounded by open living and workspace areas, equipped with various comfortable furnishings.
Cottage in Port Deposit

The River Cottage

4.94 out of 5 average rating, 357 reviews
Top Guest favourite
The little house is nestled in a serene rural setting, surrounded by greenery and farmland. A gravel pathway leads up to the front door, flanked by simple flower pots. The landscape features open fields in the background, enhancing the peaceful ambience.
Tiny home in Cambridge

The Little House on the Farm, Water Access

4.98 out of 5 average rating, 247 reviews
Top Guest favourite
The historic log home features a stone chimney and a welcoming porch with wooden railings. The structure showcases a blend of logs and stone, with large windows allowing for natural light. Surrounding green landscapes enhance the rural charm of the property.
Cabin in Forest Hill

1765 Log Home in a Peaceful Setting

5.0 out of 5 average rating, 262 reviews
Top Guest favourite
The exterior of the cottage is framed by lush greenery and features a welcoming white facade with green trim. Soft outdoor lighting illuminates the entrance, while flower bushes add a touch of nature to the charming setting.
Cottage in Reisterstown

Unique Tiny House Getaway on An Historic Farm

4.92 out of 5 average rating, 106 reviews
Guest favourite
A wooden pier extends over the calm waters, flanked by lush greenery. Small boats are visible moored along the dock. The sky is bright with a few scattered clouds, creating a peaceful atmosphere at the shoreline.
Home in Lusby

Spacious Lakefront Cottage w/ Private Pier

4.85 out of 5 average rating, 86 reviews
Top Guest favourite
Two white Adirondack chairs are positioned on a grassy area, offering a view of a calm river. A private dock extends into the water, surrounded by natural greenery and a tree. Clear skies and distant figures can be seen near the dock.
Home in Dunnsville

Holly Bluff Bungalow

4.96 out of 5 average rating, 78 reviews
Superhost
Home in Stevensville

Kent Island Luxury Waterfront

4.63 out of 5 average rating, 38 reviews
Top Guest favourite
Home in Centreville

Family Retreat at Historic Lansdowne Manor

5.0 out of 5 average rating, 63 reviews

Quick stats about farmstay rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 60 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $17 NZD per night before taxes and fees

  • Verified guest reviews

    Over 4,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chesapeake Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore