A beach with several boats and people fishing.

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13 Aug - 14 Aug
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Stay near popular Deal Island attractions

Crab Island

Commune with nature and explore the great outdoors at Crab Island during your travels in Deal Island. Discover the sunsets in this relaxing area.
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Franks Island

Commune with nature and explore the great outdoors at Franks Island during your travels in Deal Island. Discover the sunsets in this relaxing area.
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Rock Island

Commune with nature and explore the great outdoors at Rock Island during your travels in Deal Island. Discover the sunsets in this relaxing area.
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Learn more about Deal Island

Watermen's heritage tours reveal the authentic Chesapeake Bay lifestyle while you learn about the island's historic skipjack fleet. Explore pristine marshlands by kayak or visit the Deal Island Wildlife Management Area where birdwatchers spot rare migratory species.

See all hotels in Deal Island
A beach with several boats and people fishing.

Top Deal Island Hotel Reviews

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

10/10 Excellent
"Perfect location to all the seafood spots"
Sunshine 1-night trip
Posted 1 day ago
Rodeway Inn at Somers Cove Marina
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

10/10 Excellent
"Was a wonderful stay, our daughter got married on the island and reception at the fire hall, all we needed was right on the island and our daughter was able to get ready and the house and all went perfectly. P.S. her husbands grandmother and uncle leave right across the street, which was unbelievable."
Jesse 3-night trip
Posted 3 days ago
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

10/10 Excellent
"The owner, Chris, was very helpful with what we needed to bring, which was so helpful. Would definitely recommend. House was clean and well stocked."
Denise B. 2-night trip
Posted 11 days ago
Historic home on Smith Island w/ dock!
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10/10 Excellent
"This was a return trip for me, as always the property was clean, comfortable, quiet, The communication with the host was excellent, and we’ll definitely be back in the future to enjoy the gem that Hoopers Island is. Thank you for sharing your property again."
John M. 2-night trip
Posted 1 month ago
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Beautiful Bayfront with Sanctuary Private Beach

Beautiful Bayfront with Sanctuary Private Beach

8/10 Good
"Place is nice and big. It’s in a quiet town which is what we were looking for. The place has well water but when you turn it on it smells like straight rotten eggs. It was definitely hard to shower because that’s all you can smell. During our stay we had some electrical issues but the owner was very attentive to it. Just wish it was caught before our stay. Overall we had a nice stay!"
Annamae N. 4-night trip
Posted 1 month ago
Beautiful Bayfront with Sanctuary Private Beach
Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

10/10 Excellent
"I've been a vrbo rentee for 10 years and have rented different waterfront houses and so far this house was the best in terms of the ff:-The layout of the is excellent. If this was my house, I would design it same way.-dock is close enough but could have been bigger but it's ok also the way it is.-3 bathrooms is superb!- 2 living rooms, an enclosed patio and open patio with hot pool are extra perks.- it's not so isolated and next door neighbors are friendly enough - kayaks x2 was great as some houses don't even have one or only have one-their shed are full of stuff like bicycle, fishing rods, nets, etc which we didn't have to use as we brought ours-tv x3 excellent -internet connection was reliable - Air con is centralized and no problem especially when heat was at it's highest - grill was gas and loaded-linens provided n toiletries lasted for 3 days and that's ok.- this is the best: there was a wooden path to the docking area. We don't need to walk to moist grass especially in the morning.- this is the first house where I didn't even experience bugs around the house including the dock area. There were so many dragonflies that kept mosquitoHere are a few of improvements I can suggest but definitely not a deal breaker:-sink at the dock can be useful if water is running and sink is cleared of old stuff clutter. We couldn't use it.-area around house can be cleaned of old grass -the 2 patios can be cleaned better. I think the cleaners just omit to clean these."
Alicia J. 4-night trip
Posted 1 month ago
Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District
Deal Island Bay Cottage

Deal Island Bay Cottage

10/10 Excellent
"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!!"
Harold B. 5-night trip
Posted 2 months ago
Deal Island Bay Cottage
 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.

10/10 Excellent
"Helpful host, clean house, peaceful location! "
Jennifer P. 2-night trip
Posted 9 months ago
Tangier Escape, great place get away from it all on Deal Island, MD.

More cheap stays in Deal Island

Econo Lodge Princess Anne

Econo Lodge Princess Anne

10936 Market Lane US 13 Princess Anne MD
£59
13 Sept - 14 Sept
includes taxes & fees
6.6/10 (707 reviews)
Econo Lodge Princess Anne
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

30359 Mt. Vernon Road Princess Anne MD
£62
17 Aug - 18 Aug
includes taxes & fees
6.8/10 (68 reviews)
Americas Best Value Inn Princess Anne
Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

304 Prosperity Lane Fruitland MD
£88
23 Aug - 24 Aug
includes taxes & fees
Hampton Inn & Suites Salisbury/Fruitland
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

700 Norris Harbor Dr Crisfield MD
£90
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (161 reviews)
Rodeway Inn at Somers Cove Marina
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

125 Newtowne Blvd Pocomoke City MD
£105
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (978 reviews)
Best Western Plus Pocomoke City

Frequently asked questions

What is the best area to stay in Deal Island?
The best area to stay in Deal Island is the village of Chance, which is the main settlement on the island.Chance is the heart of Deal Island, known for its strong waterman culture and direct access to the Tangier Sound. It's a small, quiet community with a few local businesses, including a general store and a couple of seafood eateries. The main road, Deal Island Road, runs through the village, connecting it to the mainland. The area is characterised by its waterfront homes, boat docks, and views of the Chesapeake Bay.Couples looking for a peaceful retreat will find Chance ideal. It offers a chance to disconnect and enjoy the natural beauty and calm of the Eastern Shore. You can spend your days crabbing, fishing, or simply watching the watermen at work. The relaxed pace and scenic surroundings make it great for a quiet getaway.Solo travellers seeking a unique and authentic experience will also appreciate Chance. The community is welcoming, and you'll get a real sense of traditional Chesapeake Bay life.
When is the best time to go to Deal Island?
The best time to visit Deal Island is during the spring and autumn months, specifically from April to May and September to October.These periods offer pleasant weather, avoiding the high humidity and heat of summer and the chill of winter. You'll find the conditions ideal for outdoor activities like crabbing, fishing, and exploring the island's natural beauty without the discomfort of extreme temperatures. The island's waterways are calmer, making boat trips more enjoyable, and the wildlife is often more active.For those interested in local culture, visiting in September allows you to experience the annual Skipjack Race and Festival. This event is a central part of Deal Island's heritage, celebrating its maritime traditions with boat races, local food, and crafts.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Deal Island.
How much is the nightly rate at a Deal Island hotel?
Prices for hotels in Deal Island often vary, but you can find a great deal from £59 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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