Vacation rentals in Smith Island

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Top-rated vacation rentals in Smith Island

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Guest favorite

Cottage in Heathsville

4.94 out of 5 average rating, 179 reviews

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

Mar 4 – 11

ﺩ.ﺇ450 per night

Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 293 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.

Aug 1 – 8

ﺩ.ﺇ303 per night

Guest favorite

Farm stay in Onancock

4.99 out of 5 average rating, 174 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!

Oct 16 – 23

ﺩ.ﺇ654 per night

Guest favorite

Home in Reedville

4.97 out of 5 average rating, 118 reviews

Sunkissed Cottage-private, natural waterfront home

Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

Aug 13 – 20

ﺩ.ﺇ634 per night

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 181 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Feb 3 – 10

ﺩ.ﺇ1,236 per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 316 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!

Nov 21 – 28

ﺩ.ﺇ323 per night

Guest favorite

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

Sep 1 – 8

ﺩ.ﺇ663 per night

Guest favorite

Cottage in White Stone

4.91 out of 5 average rating, 298 reviews

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Oct 6 – 13

ﺩ.ﺇ442 per night

Guest favorite

Cabin in Reedville

4.97 out of 5 average rating, 188 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.

Nov 19 – 26

ﺩ.ﺇ590 per night

Guest favorite

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

Dec 11 – 18

ﺩ.ﺇ490 per night

Guest favorite

Home in Tangier

4.98 out of 5 average rating, 139 reviews

Watermans Hideaway, Tangier Island, Chesapeake Bay

The Waterman’s Hideaway is a two story, coastal inspired home located on main street at the center of town and a short walk from Tangier’s restaurants, gift shops and tour boat docks. Guests can enjoy the deck overlooking the spacious backyard or lounge under the shade tree at the front of the property where they can interact with the locals passing bye as they go about their daily routines.

Apr 1 – 8

ﺩ.ﺇ635 per night

Guest favorite

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.

Apr 17 – 24

ﺩ.ﺇ524 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Smith Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Smith Island

Guest favorite

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Aug 21 – 28

ﺩ.ﺇ587 per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

Sep 16 – 23

ﺩ.ﺇ326 per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

Aug 31 – Sep 7

ﺩ.ﺇ395 per night

Guest favorite

Home in Heathsville

4.93 out of 5 average rating, 122 reviews

Water ft Chesapeake Bay DREaM Vacation Dock Kayaks

Jan 1 – 8

ﺩ.ﺇ1,370 per night

Guest favorite

Cottage in Reedville

4.95 out of 5 average rating, 114 reviews

Bull Neck Cottage

Oct 4 – 11

ﺩ.ﺇ378 per night

Guest favorite

Tiny home in Accomac

4.93 out of 5 average rating, 440 reviews

Little Red House on a Farm - Quiet Rural Waterview

Apr 11 – 18

ﺩ.ﺇ453 per night

Guest favorite

Guesthouse in Saluda

4.93 out of 5 average rating, 469 reviews

Wooded Cabin retreat on fresh water pond

Feb 27 – Mar 6

ﺩ.ﺇ355 per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 312 reviews

Coastal Treetop Retreat w/ Private Beach Access

Jan 19 – 26

ﺩ.ﺇ467 per night

Show all

Quick stats about vacation rentals in Smith Island

Total rentals
10 properties
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
740 reviews
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Smith Island?
Experience the best of Smith Island with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Smith Island?
Smith Island has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Smith Island

Top-rated vacation rentals in Smith Island

Cottage in Heathsville

Tiny home in Saint Inigoes

Farm stay in Onancock

Home in Reedville

Cottage in Westover

Apartment in Lexington Park

Cottage in Onancock

Cottage in White Stone

Cabin in Reedville

Cottage in Saxis

Home in Tangier

Tiny home in Solomons

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Smith Island vacation rentals

Other great vacation rentals in Smith Island

Home in Crisfield

Cottage in California

Tiny home in Cambridge

Home in Heathsville

Cottage in Reedville

Tiny home in Accomac

Guesthouse in Saluda

Loft in Lusby

Quick stats about vacation rentals in Smith Island

Total rentals

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Smith Island?

Are there family-friendly vacation rentals in Smith Island?

Destinations to explore