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, 178 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).

Sep 14 – 21

G$25,621 GYD 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

G$17,193 GYD 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!

Jan 15 – 22

G$37,115 GYD 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 11 – 18

G$36,654 GYD 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 16 – 23

G$70,185 GYD per night

Guest favorite

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Nov 25 – Dec 2

G$33,308 GYD per night

Guest favorite

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!

Nov 10 – 17

G$18,327 GYD 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

G$37,623 GYD 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

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Aug 23 – 30

G$22,299 GYD 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!

Feb 5 – 12

G$25,073 GYD 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.

Mar 31 – Apr 7

G$36,028 GYD 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.

Nov 21 – 28

G$29,757 GYD 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

Cottage in Saxis

4.87 out of 5 average rating, 204 reviews

ISLAND SUNSETS Near Chincoteague Island

Dec 10 – 17

G$27,832 GYD per night

Guest favorite

Home in Heathsville

4.93 out of 5 average rating, 122 reviews

Water ft Chesapeake Bay DREaM Vacation Dock Kayaks

Nov 16 – 23

G$76,248 GYD 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

Dec 12 – 19

G$25,481 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

Nov 5 – 12

G$18,502 GYD per night

Guest favorite

Cottage in Reedville

4.95 out of 5 average rating, 114 reviews

Bull Neck Cottage

Sep 9 – 16

G$21,368 GYD per night

Guest favorite

Cabin in Reedville

4.97 out of 5 average rating, 188 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Oct 29 – Nov 5

G$35,558 GYD per night

Guest favorite

Guesthouse in Saluda

4.93 out of 5 average rating, 469 reviews

Wooded Cabin retreat on fresh water pond

Apr 7 – 14

G$20,368 GYD per night

Guest favorite

Cabin in Deltaville

4.97 out of 5 average rating, 253 reviews

"The Little Red Cabin" aka The Galley

Nov 16 – 23

G$23,069 GYD 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
G$12,509 GYD 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

Home in Crisfield

Apartment in Lexington Park

Cottage in Onancock

Tiny home in Cambridge

Cottage in White Stone

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

Cottage in Saxis

Home in Heathsville

Tiny home in Accomac

Cottage in California

Cottage in Reedville

Cabin in Reedville

Guesthouse in Saluda

Cabin in Deltaville

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