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Tiny house holiday rentals in Delmarva Peninsula

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Top-rated tiny house rentals in Delmarva Peninsula

Guests agree: These tiny house rentals are highly rated for location, cleanliness and more.

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Tiny home in Cambridge

4.89 out of 5 average rating, 498 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

8–15 Jul

$155 NZD per night

Guest favourite

Tiny home in Accomac

4.93 out of 5 average rating, 441 reviews

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a tiny house with big charm. This rural cottage on a 50 acre farm is nestled between peaceful fields, woods, marsh and creek. Curated with hygge comfort and efficiency in mind, you'll love the natural light and serene decor. • Epic stargazing • Heavenly private outdoor shower • Firepit with wood provided • Ample open spaces • Peace and quiet for sleeping • Comfy patio seating for chilling, coffee, and cocktails • Fast Starlink WIFI. • Proud Superhost for 10+ years!

23–30 Mar

$247 NZD per night

Guest favourite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 294 reviews

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

Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs 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.

8–15 Aug

$156 NZD per night

Guest favourite

Houseboat in Grasonville

4.99 out of 5 average rating, 116 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

10–17 Feb

$345 NZD per night

Guest favourite

Tiny home in Snow Hill

4.89 out of 5 average rating, 226 reviews

Private cottage and gardens/comfortable queen bed.

Private cottage and gardens, comfortable Queen bed, full bath and kitchenette, within walking distance to historic Snow Hill. 30 min. drive to Ocean city and Assateague Island National park. This cottage was once a old school woodworking shop which is now on display at the old iron furnace town museum nearby. This beautiful three hundred year old town sits on the beautiful Pocomoke river with canoe, kayak, and bike rentals. Museums, art galleries, speciality shops, food and entertainment.

14–21 Aug

$234 NZD per night

Guest favourite

Guesthouse in White Stone

4.98 out of 5 average rating, 145 reviews

Waterfront Guesthouse I on the Rappahannock

The “Marsh 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 beautiful water views and includes access to our private beach & dock with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and attached 1/2 bath.

5–12 Mar

$388 NZD per night

Guest favourite

Home in Ocean View

4.92 out of 5 average rating, 530 reviews

Tiny House at Good Earth, near Bethany Beach

A custom-built "Tiny House" located right between our new dinner theater and our garden dining area. True to the show "Tiny House Nation"; cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TVs and internet in the units but the quality of service is not guaranteed. We are in a rural area and sometimes it's slow or not working at all. If TV and internet are super important for your stay we may not be the right fit.

27 Dec – 3 Jan

$231 NZD per night

Guest favourite

Tiny home in Selbyville

4.98 out of 5 average rating, 213 reviews

Destination Location! Farm Animals, Tours, Beaches

Scratch staying in a tiny house off your bucket list! Escape the Ocean City crowds and slow life down at this Garden Hideaway. Situated on a ranch just minutes from the beach, this unique home has a barnyard of fuzzy animals ready to greet you each day. Curated to both inspire joy and create presence, enjoy a simple morning and sip coffee with Fonzie the alpaca, Charlotte the mini-pig and a front yard of silly goats sure to entertain. This is a magical stay that we know you'll love!

12–19 Oct

$251 NZD per night

Guest favourite

Guesthouse in Onancock

4.93 out of 5 average rating, 205 reviews

NEWLY Renovated -- Waterfront Getaway

Renovation - Siding, windows, doors, landing/stairs, flooring, foam insulation, paint, min-split AC/heat unit. Nestled comfortably on an acre along Onancock Creek, this quiet one-room guest house boasts a full kitchen, Serta queen size bed, TV/internet, and incredible scenery of the creek. Spend a weekend exploring historic Onancock, with its unique shops and variety of cuisine, or rent kayaks in town for a relaxing cruise on the creek to watch the sunset over the Chesapeake Bay.

11–18 Feb

$239 NZD per night

Guest favourite

Tiny home in Cape Charles

4.98 out of 5 average rating, 275 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.

21–28 Jan

$491 NZD per night

Guest favourite

Cottage in Saint Michaels

4.99 out of 5 average rating, 137 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.

6–13 Aug

$985 NZD per night

Guest favourite

Cottage in Onancock

4.97 out of 5 average rating, 198 reviews

Escape to the Eastern Shore - Upscale Waterfront

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

24 Nov – 1 Dec

$347 NZD per night

Holiday rentals for every style

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Popular amenities for Delmarva Peninsula tiny house rentals

Free parking on premises

Air conditioning

Family-friendly tiny house rentals

Home in Rehoboth Beach

4.79 out of 5 average rating, 621 reviews

Contemporary 1 Bedroom 2 level home

3–10 Feb

$217 NZD per night

Guest favourite

Cabin in Lovettsville

4.97 out of 5 average rating, 120 reviews

Rustic cabin + modern luxury in Lovettsville

20–27 Oct

$265 NZD per night

Guest favourite

Tiny home in Purcellville

4.96 out of 5 average rating, 314 reviews

Remote Tiny House in Purcellville

5–12 Mar

$288 NZD per night

Guest favourite

Guest suite in Richmond

4.97 out of 5 average rating, 589 reviews

Forest Hill Modern Guest House

30 Jul – 6 Aug

$317 NZD per night

Guest favourite

Apartment in Lewes

4.97 out of 5 average rating, 522 reviews

Sandy Blessings

15–22 Oct

$275 NZD per night

Guest favourite

Castle in Fredericksburg

4.95 out of 5 average rating, 552 reviews

Little Castle

1–8 Nov

$210 NZD per night

Guesthouse in Washington

4.9 out of 5 average rating, 411 reviews

Ingraham Alley Inn - A Quiet & Cozy Micro House

5–12 Sep

$217 NZD per night

Guest favourite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

22–29 Oct

$355 NZD per night

Tiny house rentals with a patio

Guest favourite

Guesthouse in Myersville

4.93 out of 5 average rating, 191 reviews

Spruce Run Cottage, Farm stay on Catoctin Mountain

1–8 Jul

$182 NZD per night

Guest favourite

Guesthouse in Yorktown

4.97 out of 5 average rating, 203 reviews

Charming Yorktown Battlefield Cottage

26 Sep – 3 Oct

$202 NZD per night

Guest favourite

Barn in Richmond

4.92 out of 5 average rating, 224 reviews

Cozy Carriage House Conversion

13–20 Jul

$265 NZD per night

Guest favourite

Tiny home in Purcellville

4.98 out of 5 average rating, 130 reviews

King Bed-Tiny Home-Fire Pit-Historic Farm Stay

10–17 Sep

$363 NZD per night

Guest favourite

Treehouse in Richmond

4.88 out of 5 average rating, 121 reviews

Romantic Treehouse for 2 (No Kids) in Little Farm

5–12 Feb

$214 NZD per night

Guest favourite

Tiny home in Fredericksburg

4.87 out of 5 average rating, 136 reviews

Delightful Tiny Cottage in Historic Downtown

13–20 Jul

$280 NZD per night

Guest favourite

Guesthouse in Richmond

4.95 out of 5 average rating, 106 reviews

Not-so-Tiny Home by Scotts Addition w/ Pvt Parking

13–20 Sep

$340 NZD per night

Guest favourite

Loft in Pocomoke City

4.98 out of 5 average rating, 57 reviews

Cozy Barn Loft: Country Views & Central to Beaches

18–25 Jan

$288 NZD per night

Tiny house rentals with outdoor seating

Guest favourite

Cabin in Cape Charles

4.96 out of 5 average rating, 100 reviews

Ultimate Cabin Farm Stay Cape Charles

12–19 Jan

$427 NZD per night

Guest favourite

Cottage in Lower Township

5.0 out of 5 average rating, 146 reviews

Octopus Cottage: Hot Tub | Kayaks | Fire Pit

4–11 Mar

$919 NZD per night

Guest favourite

Tiny home in Deltaville

4.99 out of 5 average rating, 143 reviews

Teenie Weenie Luxury Guest House in Deltaville

29 Nov – 6 Dec

$247 NZD per night

Guest favourite

Tiny home in West Point

4.95 out of 5 average rating, 241 reviews

The Cozy Cottage At Grateful Meadows

31 Jul – 5 Aug

$307 NZD per night

Guest favourite

Guesthouse in Annapolis

4.9 out of 5 average rating, 209 reviews

Calico Cottage Guest House, king bed, free parking

26 Mar – 2 Apr

$203 NZD per night

Guest favourite

Cottage in Urbanna

4.99 out of 5 average rating, 134 reviews

Little Dipper -private beach,Kayaks & paddleboards

24–31 Oct

$410 NZD per night

Guest favourite

Guesthouse in Dennis

4.94 out of 5 average rating, 288 reviews

Shore Cottage~minutes to beach, wine, brews

14–21 Jan

$310 NZD per night

Guest favourite

Guesthouse in Hammonton

4.99 out of 5 average rating, 221 reviews

The Little House

8–15 Nov

$166 NZD per night

Destinations to explore