Holiday houses in Assawoman

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Assawoman

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Tiny home in Accomac

4.93 out of 5 average rating, 440 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!

5 – 12 Dec

$1,600 AUD total

Guest favourite

Farm stay in Onancock

4.99 out of 5 average rating, 173 reviews

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!

27 Nov – 4 Dec

$2,131 AUD total

Guest favourite

Home in Chincoteague Island

4.97 out of 5 average rating, 179 reviews

★ Jay’s Waterfront Retreat: Private Dock- Kayaks-Fire Pit-Bikes-Beach-Pet Friendly ★

Fully equipped 1000 sf home-3 Bdrm residence-with fire pit, 2 kayaks, 4 bikes & Private Dock. Linens & towels included Jay's Retreat is at nature's front door within a few miles from Assateague National Seashore (the beach), home of the world famous Chincoteague Ponies. Enjoy: Swimming in the bay and ocean Bicycling Fishing, crabbing, clamming Kayaking, paddle boarding; boating Hiking Bird Watching Nature photography Hunting Nature Trails Great Restaurants & Brew Pub Boat Tours Ponies

29 Jan – 5 Feb

$1,699 AUD total

Guest favourite

Home in Accomac

4.98 out of 5 average rating, 218 reviews

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.

12 – 19 Nov

$2,024 AUD total

Guest favourite

Home in Cape Charles

4.99 out of 5 average rating, 104 reviews

Modern Private Beach House close to Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

17 – 24 Dec

$10,530 AUD total

Guest favourite

Guesthouse in Onancock

4.94 out of 5 average rating, 204 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.

7 – 14 Aug

$1,506 AUD total

Guest favourite

Cottage in Onancock

4.97 out of 5 average rating, 195 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

1 – 8 Sept

$2,246 AUD total

Guest favourite

Apartment in Lexington Park

5.0 out of 5 average rating, 315 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

1 – 8 Oct

$1,097 AUD total

Guest favourite

Guest suite in Chincoteague

4.93 out of 5 average rating, 224 reviews

Baywatch North-Waterfront & Roaming Ponies

This is a lovely space! 2 queen bedroom unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, patio cooking area shared with upstairs unit, bbq grill, fantastic view, beach items, plenty of parking, private lane, very quiet out of the way of everything, super laid back host living in the other portion of the house. Labrador and cat on premises, ponies on premises!

21 – 28 Oct

$1,341 AUD total

Guest favourite

Cottage in Saxis

4.87 out of 5 average rating, 204 reviews

ISLAND SUNSETS Near Chincoteague Island

1 - Story Near Chincoteague Island Virginia Assateague Beach NASA Wallops Island, Va. Onancock, Va Waterman’s Fishing Village Surrounded by Water on three sides & Virginia Wildlife Refuge on fourth side. 400 ft. Walking distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, Ice Cream Shop, 2 Restaurants, Museum, Multiple Seafood Shantys

8 – 15 Dec

$1,684 AUD total

Guest favourite

Tiny home in Solomons

4.95 out of 5 average rating, 538 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

4 – 11 Dec

$1,753 AUD total

Guest favourite

Tiny home in Machipongo

4.98 out of 5 average rating, 254 reviews

Machipongo Glamper

Close your eyes. Imagine a salty breeze and a view of a vineyard from your spot tucked into the back of our rural 5 acre spot. The stars are brighter, the clams are saltier, and the pace is slower. At night, the stars go on forever and in morning a perfect view of the sun rising over the neighbor’s field.

21 – 28 Nov

$851 AUD total