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Tylerton Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Tylerton vacation rentals

A marina at sunset with boats docked and buildings in the background.

1. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$303 nightly
The price is $334
Oct 16 - Oct 17
Total with taxes and fees
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A row of white houses by a lake with American flags.

2. Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
Smith Island
9.4 out of 10, Exceptional, (3 reviews)
"This is a great place to stay on Smith Island. Easy access to most areas. The Golf cart is also nice to have. The house has everything you need and many extras too! Highly recommend a visit here."
United States
Margaret A.
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

3. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
$176 nightly
The price is $187
Oct 18 - Oct 19
Total with taxes and fees
Cottage near the Bay
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

4. Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (27 reviews)
"I always stay here when I come for work it’s a pretty nice place quiet and clean I highly recommend it to everyone it’s visiting"
United States
Luis A.
$237 nightly
The price is $254
Oct 18 - Oct 19
Total with taxes and fees
Newly updated 3 bedroom cottage with Solo Stove fire pit
A sandy beach with footprints, a pier in the distance, and a clear sky.

5. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$233 nightly
The price is $247
Oct 22 - Oct 23
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

6. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
Tangier
10.0 out of 10, Exceptional, (22 reviews)
"Ken & and family were wonderful hosts, his communication was perfect! The house was clean and a great place to stay. We had a wonderful weekend and can't wait to come back."
United States
Tim B.
$368 nightly
The price is $406
Oct 16 - Oct 17
Total with taxes and fees
Unique Tangier Cottage w/ Chesapeake Bay Views!
A white door with a glass panel and a sunflower decoration, flanked by two wall-mounted lanterns.

7. Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom

Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
Reedville
10.0 out of 10, Exceptional, (29 reviews)
"The host was amazing and the house was just as amazing."
United States
Mark R.
$344 nightly
The price is $369
Oct 18 - Oct 19
Total with taxes and fees
Reelin&Relaxin Spacious Farmhouse Reedville, VA Sleeps 8: 3 Bdrm 2 full bathroom
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$245 nightly
The price is $259
Oct 18 - Oct 19
Total with taxes and fees
Deal Island Bay Cottage
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

9. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
3.0 star property
Tangier
$358 nightly
The price is $395
Oct 16 - Oct 17
Total with taxes and fees
Unique Tangier Cottage w/ Chesapeake Bay Views!
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

10. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (20 reviews)
"Was very cozy and comfortable."
United States
sandi c.
$394 nightly
The price is $435
Oct 26 - Oct 27
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
A covered outdoor deck with a view of a lake, wooden furniture, and a ceiling fan.

11. Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!

Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Reedville
9.0 out of 10, Wonderful, (2 reviews)
"We had a great time. The host was very welcoming and helpful. Hope to go back again."
United States
holly u.
$1,271 nightly
The price is $1,363
Oct 21 - Oct 22
Total with taxes and fees
Bayfront Oasis with Heated Pool, Hot Tub & Playground! Family & Pet friendly!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Tylerton Hotel Reviews

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

10/10 Excellent
"The cottage was very clean and well appointed! Cozy and relaxing with the bay mere steps away! We enjoyed the beach and the fishing was good. Great communications with Missy, checkin and checkout were a breeze. We will consider this cottage for our annual trip next year. We highly recommend staying at Bay Side Retreat!"
Keith B. 3-night trip
Posted 1 day ago
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Find out more about Tylerton

Everything you need to know about Tylerton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tylerton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tylerton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tylerton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tylerton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tylerton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tylerton rentals

At Expedia, we put the best Tylerton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tylerton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tylerton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tylerton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Tylerton?

Yes, we give you a choice of vacation rentals near top local attractions in Tylerton, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Tylerton?

Beautiful Bayfront with Sanctuary Private Beach : This vacation home near Tylerton offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Tylerton?

While you're exploring the area, Smith Island and Tangier Island Beach are a couple of picturesque spots to get outside and enjoy nature. Tylerton County Dock and Crisfield City Dock are a couple of places you'll find in the larger area.

What’s a vacation rental in Tylerton like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Tylerton. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a small group gathering.