
Tiny house holiday rentals near Chesapeake Bay
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Top-rated tiny house 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. • 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 12+ years

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

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Waterfront Guesthouse I on the Rappahannock
The “Bay 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 a beautiful Bay view and includes access to our private beach & dock (w/ guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath w/ jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and 1/2 bath.

Stargazer Tiny Cabin
(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

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.

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.

Long Beach Cottage, Hot Tub, Beachfront
The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

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.

Tiny House Treasure on the Rappahannock River
The Riverbunk is located on the Rappahannock River in Colonial Beach, Virginia. The scenic River is home to Eagles, ospreys and great blue herons. The river offers the perfect kayaking experience and for boaters, a boat launch is within walking distance. Fishing, hunting, hiking and sightseeing are popular in this area. We are 420-friendly where smoking is allowed outside. The rural area is perfect for quiet downtime and fun activities.
Popular amenities for tiny house rentals near Chesapeake Bay
Family-friendly tiny home rentals

"ON THE ROCKS CABIN" the perfect getaway for 2!

The Bohemian Rhapsody

🌅🎢Bungalow 1 block to boardwalk on 4th st!

Marshfield Guesthouse on river near Williamsburg

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

Private cottage and gardens/comfortable queen bed.

Tiny A-Frame Retreat in the Woods

Forest Hill Modern Guest House
Tiny home rentals with a patio

Cozy Woodland Cottage

Log Out

Summer Camp Tiny Cottage Walk to the beach & shops

*Peaceful *Newly *Renovated 2 Bedroom 1 Bath

Tree house resort spa with sauna

Private Cottage * 1 bedroom+loft * Rehoboth Beach

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Carriage House Conversion
Tiny home rentals with outdoor seating

Tiny House at Good Earth, near Bethany Beach

Calico Cottage Guest House, king bed, free parking

Unique, luxurious creekside stay in Cape Charles

Nautical Charm and Relaxing Waterview!

Historic St.Mary's City at the Lazy Bear Cottage

Tiny house w/ Pool on water near Beaches / turf

NEWLY Renovated -- Waterfront Getaway

The Barkin’ B & B
Other tiny house holiday rentals

Luxurious 1Bed Carriage House, 1.5 Blocks to Metro

Private Small Apt with parking spot.

Home away from home

The Little House

Rehoboth Beach Farmhouse Studio *Pet Friendly*

Sunnyside Up - Dog Friendly Waterfront Cottage

Ingraham Alley Inn - A Quiet & Cozy Micro House

Eastern Shore Romantic Waterfront Getaway Upscale
Quick stats about tiny house rentals near Chesapeake Bay

Total holiday rentals
Explore 50 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 5,410 verified reviews to help you choose

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.9 Average rating
Chesapeake Bay stays are highly rated by guests – averaging 4.9 out of 5!
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- Tiny house rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- The Mariners' Museum
- Nauticus
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- Hampton University
- Cape Henry Light House
- Chrysler Hall





