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Farm-stay vacation rentals near Chesapeake Bay

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Top-rated farm-stay rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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

ValueFamilyBathroom

4.98 out of 5 average rating, 204 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.

ValueLocationBathroom

5.0 out of 5 average rating, 438 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!

LocationFamilyParking

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

FamilyLocationHospitality

4.99 out of 5 average rating, 134 reviews
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.

LocationFamilyNearby

4.97 out of 5 average rating, 315 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!

LocationValueView

4.99 out of 5 average rating, 354 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.

FamilyLocationSleep quality

5.0 out of 5 average rating, 113 reviews
Top guest favourite
Two blue Adirondack chairs are positioned on a leaf-covered area, facing a tranquil body of water. Surrounding trees provide a natural frame, with autumn foliage adding warm colors. In the background, a wooden dock and shelter are visible along the water's edge.
Cottage in Annapolis

Waterfront farm retreat for vacation & telework

Stay on 125-acre Hollywood Farm in a beautiful and quiet home surrounded by water and woods. Our airy, mid-century renovated cottage feels like a sanctuary, tucked away on a peninsula on one of the largest tracts of conservation land in Maryland. This cozy, light-filled space is small but spacious, allowing you to work peacefully from home with a full desk and excellent high-speed internet access. Plus, there's a dock, kayaks, and lots of outdoor space for children and pets to run around in.

FamilyValueKitchen

4.98 out of 5 average rating, 162 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.

LocationValueView

4.97 out of 5 average rating, 627 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

Welcome to our 1900's farmhouse. This home has been lovingly updated and maintained over the past century, and sits on 7.5 acres. While it is private and peaceful, its location is minutes away from everything making it easy to get around. Enjoy spacious living and endless outdoor fun in our dedicated game barn (ping pong, cornhole!) and large pastures (frisbee golf, soccer!). This family-friendly home blends historic charm with modern comforts, perfect for creating unforgettable memories.

LocationFamilyBackyard

4.93 out of 5 average rating, 141 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!

ValueLocationBathroom

4.98 out of 5 average rating, 156 reviews
Top guest favourite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny homes in Cape Charles

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.

FamilyLocationHeating

4.98 out of 5 average rating, 364 reviews

Popular amenities for farm-stay rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly farm stay accommodations

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

LocationFamilyQuiet

4.97 out of 5 average rating, 707 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 homes in West Point

The Cozy Cottage At Grateful Meadows

LocationFamilyKitchen

4.96 out of 5 average rating, 299 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.

FamilyValueCheckout

4.98 out of 5 average rating, 310 reviews
Guest favourite
Farm stay in Heathsville

Fleets Cove Farm *PETS STAY FREE*

ValueLocationDecor

4.98 out of 5 average rating, 125 reviews
Guest favourite
Tiny homes in Accomac

Little Red House on a Rural Farm for Stargazing

FamilyLocationBathroom

4.94 out of 5 average rating, 544 reviews
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!

FamilyLocationSleep quality

4.99 out of 5 average rating, 162 reviews
Top guest favourite
A charming cottage with a light green facade is framed by lush greenery. A set of stairs leads to the entrance. Two bicycles with bright blue frames are positioned in front, enhancing the inviting atmosphere of the outdoor space.
Cottage in Irvington

Irvington Cottage - Vineyard Birdhouse

LocationValueGetting around

4.96 out of 5 average rating, 121 reviews
Top guest favourite
A waterfront home is depicted with a blue exterior and a welcoming front porch featuring Adirondack chairs. Lush greenery surrounds the property, and a rocky shoreline is visible in the foreground. The serene setting is complemented by clear skies and distant trees.
Home in Kilmarnock

Waterman's Waypoint

LocationFamilyCheckout

4.93 out of 5 average rating, 121 reviews

Farm stay accommodations with a patio

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

FamilyLocationIndoor spaces

4.84 out of 5 average rating, 102 reviews
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

ValueFamilyCondition

5.0 out of 5 average rating, 156 reviews
Top guest favourite
A charming stone cottage is surrounded by lush greenery. The red roof contrasts with the natural landscape. A spacious deck features outdoor seating, providing a serene view of the garden and rolling grassy hills beyond.
Farm stay in Lincoln University

Pyle Cottage, circa 1750

FamilyValueSolo travel

4.97 out of 5 average rating, 203 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

FamilyLocationAccess

4.93 out of 5 average rating, 133 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.
Ranch in Selbyville

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

ValueFamilySleep quality

4.98 out of 5 average rating, 323 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

LocationFamilyLong stay

5.0 out of 5 average rating, 127 reviews
Top guest favourite
Exposed wooden beams and a high ceiling create an open atmosphere in the main area. A striking blue wall with 'JCS FARMS' lettering serves as a focal point. A staircase leads to a lower level, while natural light filters through large windows.
Home in Centreville

Modern Farmhouse near DC/Wineries/Hiking/Parks

ValueFamilyIndoor spaces

4.95 out of 5 average rating, 139 reviews
Guest favourite
The exterior of the farmhouse is presented during twilight, showcasing a charming white façade and a traditional red brick chimney. Lush greenery surrounds the home, with flowers blooming in the garden. The patio area features a dining set, enhanced by a vibrant sunset sky.
Farm stay in Elkton

Countryside-Tennis-Pool Table-Autumn Getaway!

ValueLocationWifi

4.95 out of 5 average rating, 109 reviews

Farm stay rentals with a washer and dryer

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

ValueFamilyParking

4.99 out of 5 average rating, 285 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

FamilyValueAmenities

4.92 out of 5 average rating, 197 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

ValueLocationSolo travel

4.98 out of 5 average rating, 722 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

ValueLocationWalkability

4.96 out of 5 average rating, 421 reviews
Top guest favourite
An aerial view captures the historic guest house surrounded by expansive green fields and trees. The structure features a white exterior and a dark roof. A gravel parking area accommodates several vehicles, while the rural landscape stretches into the distance.
Home in Hydes

"Merrywell"at Merryland Farm A horse lovers haven

FamilyValueGetting around

4.94 out of 5 average rating, 136 reviews
Top guest favourite
Cabin in Upperco

The Guesthouse at Downey Family Farm

ValueFamilyDecor

4.94 out of 5 average rating, 151 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

ValueLocationIndoor spaces

4.98 out of 5 average rating, 370 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

FamilyLocationQuiet

4.98 out of 5 average rating, 112 reviews

Other farm-stay vacation rentals

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 homes in Cambridge

The Little House on the Farm, Water Access

FamilyLocationLayout

4.98 out of 5 average rating, 249 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

FamilyValueQuiet

5.0 out of 5 average rating, 265 reviews
Top guest favourite
A cozy bedroom features a spacious bed adorned with a floral quilt. Nightstands with lamps sit on either side, offering soft lighting. Artwork in warm tones is displayed on the walls, complemented by a vintage mirror above the headboard. A comfortable seating area is visible in one corner.
Farm stay in Toano

Private Farm Retreat - Right Outside Williamsburg

LocationValueCheckout

4.95 out of 5 average rating, 359 reviews
Top guest favourite
The historic stone house features a large front porch with a railing and several steps leading to the entrance. Its facade includes multiple windows framed by red shutters, with a modern addition visible on one side. Lush green grass surrounds the house, adding to the rural setting.
Farm stay in Mount Airy

Poole House at Friendship Farm

FamilyLocationAccess

4.98 out of 5 average rating, 123 reviews
Top guest favourite
The image displays a wooden sign identifying Gin Lot Farms, featuring a horse silhouette. The sign is mounted on a sturdy post beside a grassy area, with a backdrop of trees and open fields visible in the distance.
Home in Fredericksburg

Private home at Gin Lot Farms

LocationFamilyParks

4.97 out of 5 average rating, 147 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

ValueLocationOutdoor spaces

4.85 out of 5 average rating, 89 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

ValueFamilyCheckout

4.96 out of 5 average rating, 79 reviews
Guest favourite
An aerial view showcases a lush landscape with rows of trees lining a pathway leading to the water. The estate is surrounded by greenery, revealing distant waterfront views that accentuate the serenity of the location.
Home in Onancock

Historic Waterfront Farmhouse and Cottage

ValueLocationView

4.9 out of 5 average rating, 92 reviews

Quick stats about farm-stay rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 60 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at $29 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,940 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Chesapeake Bay vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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