Tiny house vacation rentals near Chesapeake Bay

Tiny home in Saint Inigoes

The sun is seen shining through the branches of a tree, casting rays of light over a calm river. The water reflects the sunlight, creating a sparkling effect. A wooden pier extends into the water, surrounded by lush greenery.

4.98 out of 5 average rating, 379 reviews

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

Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

4.95 out of 5 average rating, 254 reviews

The exterior of Westview Cottage is shown, featuring a well-maintained lawn with lush greenery. Floor-to-ceiling glass doors are visible, reflecting the surrounding landscape and allowing natural light into the cottage. Trees and shrubs frame the view, enhancing the serene atmosphere.

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

4.95 out of 5 average rating, 121 reviews

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

Home in Lusby

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.

4.98 out of 5 average rating, 217 reviews

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

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!

Houseboat in Kent Narrows

A modern houseboat is anchored at the dock, featuring a covered deck with two lounge chairs. Large windows offer views of the waterfront and allow natural light into the interior. The structure sits on wooden stilts above calm waters, showcasing a serene boating environment.

4.97 out of 5 average rating, 175 reviews

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

4.95 out of 5 average rating, 140 reviews

A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.

Cottage in Hacksneck

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!

Guesthouse in White Stone

A serene sunset is captured over the water, with warm hues of orange and pink blending into a vibrant sky. Silhouettes of individuals can be seen on a dock, reflecting a peaceful evening setting near the Rappahannock River.

4.99 out of 5 average rating, 210 reviews

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.

4.95 out of 5 average rating, 225 reviews

Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and has a CHRISTMAS TREE, a PERFECT spot for a WINTRY 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

Tiny home in Cape Charles

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.

4.98 out of 5 average rating, 339 reviews

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.

Cottage in Saint Michaels

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.

4.97 out of 5 average rating, 177 reviews

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.

4.96 out of 5 average rating, 207 reviews

A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.

Cabin in Cape Charles

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 home in Westmoreland County

A charming exterior view of The Riverbunk reveals a one-bedroom house surrounded by green grass. A wooden deck is furnished with a small table and chairs, while plants are arranged in a circular bed. Bright blue skies enhance this rural setting.

4.99 out of 5 average rating, 102 reviews

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly tiny house rentals

4.9 out of 5 average rating, 317 reviews

The entrance of the guest cottage is framed by a charming picket fence, featuring a blue door and a welcoming porch. A small table with two chairs and an umbrella is situated on a wooden deck, surrounded by lush greenery.

Guesthouse in Annapolis

Calico Cottage Guest House, king bed, free parking

4.97 out of 5 average rating, 388 reviews

A treehouse is elevated among lush greenery, supported by sturdy wooden posts. A small deck extends from the entrance, leading to a spiral staircase. The exterior features dark blue siding and a metal roof, harmonizing with the surrounding forested environment.

Treehouse in Leesburg

Romantic Secluded Treehouse Stay in the Sky

4.95 out of 5 average rating, 182 reviews

A welcoming covered porch features two white chairs at the entrance of a pink home. Well-maintained shrubs and seasonal flowers border the porch area, while natural light streams through large windows, enhancing the cheerful exterior surrounded by greenery.

Guesthouse in Galesville

Nautical Charm and relaxing waterview!

Guesthouse in Fort Washington

The interior of the cottage features a vaulted wooden ceiling with beams, creating an open atmosphere. A spacious sectional sofa faces a wood-burning stove. The kitchen is equipped with modern appliances, while light streams through large windows draped in sheer curtains.

4.93 out of 5 average rating, 755 reviews

Urban Cottage,MD minutes from DC/National Harbor

4.93 out of 5 average rating, 170 reviews

A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.

Guesthouse in Bushwood

Little House by the water

4.99 out of 5 average rating, 135 reviews

Tiny home in Richmond

The Barkin’ B & B

4.94 out of 5 average rating, 513 reviews

A quaint tiny house presents a welcoming exterior with a red facade and inviting black door. Comfortable seating is arranged on green grass under a large white umbrella, surrounded by planters with flowers. Lush greenery and a pathway enhance the serene outdoor setting.

Tiny home in Accomac

Little Red House on a Farm - Quiet Rural Waterview

4.96 out of 5 average rating, 280 reviews

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

Tiny house rentals with a patio

4.95 out of 5 average rating, 186 reviews

A cozy sleeping area features a spacious bed with a quilted grey coverlet. Two decorative yellow pillows are positioned at the head of the bed. A small bedside table holds a lamp and books, while a colorful area rug adds warmth to the space.

Tiny home in Lewes

Cozy Woodland Cottage

4.8 out of 5 average rating, 187 reviews

A renovated camper features a wooden façade with a shingled design, complemented by a green door. Two outdoor chairs are positioned on a wooden deck, inviting relaxation. A flag is displayed, and trees create a natural backdrop.

Camper/RV in Ocean View

Renovated Camper at Good Earth near Bethany Beach

4.96 out of 5 average rating, 188 reviews

The cabin's entrance features a wooden gable with a distinct bird emblem. The backdrop showcases vibrant autumn foliage, with trees displaying a blend of warm orange and yellow hues against a clear sky.

Cabin in Fredericksburg

Loft Cabin *HotTub* WiFi*Firepit*Deck

Tiny home in Falls Church

The interior features a cozy living area with wooden accents and a rug centered beneath a table and chairs. An air conditioning unit is mounted above the space. A staircase leads to a lofted sleeping area, while large windows provide views of surrounding greenery.

4.98 out of 5 average rating, 169 reviews

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Tiny home in Cape Charles

A quaint 1920s house with a charming front porch is visible, featuring white siding and decorative trim. The entrance showcases a pink door framed by green foliage, with steps leading up to the porch. The front is bordered by lush greenery, adding to its inviting appearance.

4.91 out of 5 average rating, 148 reviews

Summer Camp Tiny Cottage Walk to the beach & shops

4.94 out of 5 average rating, 255 reviews

A two-story cottage is set amidst lush greenery, featuring a large upper deck that offers views of the surrounding woods. Colorful azaleas and shrubs enhance the entrance, while a gravel drive leads to the property, surrounded by trees exhibiting signs of spring.

Guesthouse in Myersville

Spruce Run Cottage, Farm stay on Catoctin Mountain

4.79 out of 5 average rating, 114 reviews

A charming blue home is captured from an angled perspective, featuring a screened porch at the front. Lush greenery surrounds the property, and even skies punctuated by clouds can be seen above. Neighboring homes are visible in a tranquil neighborhood setting.

Home in Williamsburg

*Peaceful *Newly *Renovated 2 Bedroom 1 Bath

4.96 out of 5 average rating, 175 reviews

The log cabin features a warm wooden exterior with a blue metal roof, nestled among trees. A screened porch allows for outdoor enjoyment while a fire pit is positioned nearby, surrounded by natural stone. The peaceful setting invites relaxation amidst the greenery.

Cabin in Myersville

Sleepy Hollow Log Cabin

Tiny house rentals with outdoor seating

Guesthouse in Westminster

An aerial view captures a serene landscape featuring a red barn, a charming house, and a pond. Lush green fields and trees surround the property, creating a tranquil retreat. A winding path leads through the area, emphasizing the open space and natural beauty of the surroundings.

4.87 out of 5 average rating, 359 reviews

The Pig Shed Writer’s Retreat at Barter Lady Farm

Tiny home in Cape Charles

A modern kitchen is complemented by sleek gray cabinetry and quartz countertops. Natural light fills the space through multiple windows, revealing a cozy living area with a light-colored sofa. The open loft bed above adds to the home’s efficient design.

4.89 out of 5 average rating, 201 reviews

Unique, luxurious creekside stay in Cape Charles

4.99 out of 5 average rating, 185 reviews

An outdoor patio area is shown with a wooden picnic table and several blue chairs arranged for seating. A grill is positioned nearby under a blue umbrella, with a pergola providing partial shade. Colorful flowers and greenery enhance the surrounding landscape.

Home in Leesburg

Willow’s View

4.99 out of 5 average rating, 160 reviews

The timber-framed chalet is surrounded by vibrant flower gardens, showcasing various colorful blooms. Large windows and a balcony enhance the exterior, framed by trees creating a natural backdrop. A patio area with seating is visible in the foreground, inviting guests to enjoy the peaceful surroundings.

Guesthouse in Hamilton

Trailside Chalet (A storybook chalet with hot tub)

Loft in Gloucester Courthouse

The studio apartment interior features a bright, open layout with warm wooden flooring. A dining table is set for four, illuminated by natural light from large windows. A library ladder leads to the sleeping loft, while the kitchen area is visible in the background.

4.98 out of 5 average rating, 339 reviews

Marshfield Guesthouse on river near Williamsburg

4.93 out of 5 average rating, 253 reviews

A white stairway leads to the entrance of the guest house, surrounded by trees and natural landscaping. The calm waters of Onancock Creek are visible in the background, with a glimpse of moored boats and the shoreline beyond.

Guesthouse in Onancock

NEWLY Renovated -- Waterfront Getaway

Guesthouse in Williamsburg

4.97 out of 5 average rating, 399 reviews

Freedom Cottage /King Bed-Jamestown/ Busch Gardens

4.95 out of 5 average rating, 148 reviews

A charming yellow cottage is surrounded by well-kept green grass and flower beds. The screened front porch features open spaces for seating, while a stone pathway leads to the entrance. An American flag is displayed, and trees provide a natural border around the property.

Home in Colonial Beach

Sunnyside Up - Dog Friendly Waterfront Cottage

Other tiny house vacation rentals

4.95 out of 5 average rating, 431 reviews

An aerial view captures a charming cabin nestled among trees, with a sloped roof and green accents. The landscape features a grassy area leading to a fire pit, while the surrounding woods create a serene backdrop bathed in warm afternoon light.

Cabin in Boonsboro

Little Lodge

4.95 out of 5 average rating, 125 reviews

A charming cottage is framed by a mature tree with autumn leaves. The exterior is painted in calming blue and white, featuring a welcoming porch supported by columns. A gravel path leads to the entrance, surrounded by vibrant greenery and fallen leaves.

Cottage in Aldie

Patent House at the Little River Inn

4.9 out of 5 average rating, 441 reviews

The cabin exterior features a rustic log design with a metal roof. A star motif is displayed prominently above the front porch, enhanced by flower boxes and decorative accents. The yard includes a garden area and several trees, creating a peaceful outdoor setting.

Cabin in Middletown

Charming vintage cabin in the ❤️ of Middletown.

4.97 out of 5 average rating, 352 reviews

A wooden bear sculpture stands beside the green front door, holding a carved sign that reads 'WELCOME.' The bear is positioned on a log stump, with a stone pathway and partially visible wooden porch nearby, creating an inviting entrance.

Guesthouse in Frederick

The Shady Bear Cabin

4.91 out of 5 average rating, 215 reviews

The entrance features double glass doors framed by a wooden deck. Seasonal potted plants, including vibrant flowers and greenery, are arranged on either side, while a small pumpkin adds a festive touch. A decorative light fixture hangs nearby, enhancing the welcoming appearance.

Cottage in Glen Burnie

Home away from home

Tiny home in Ellicott City

A colorful living space features a turquoise sectional sofa adorned with yellow and white pillows. A patterned area rug lies beneath a glass coffee table. Natural light filters through sheer curtains, highlighting shelves with decorative items. A spiral staircase leads to the upper level.

4.93 out of 5 average rating, 246 reviews

The Duchess of Font Hill {a tiny house}

Place to stay in Frederick

A tranquil outdoor seating area features two wooden Adirondack chairs facing a fire pit made of stone. The tiny A-frame cabin is visible in the background, surrounded by tall trees in a lush woodland setting.

4.9 out of 5 average rating, 143 reviews

Tiny A-Frame Retreat in the Woods