A beach with several boats and people fishing.

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Oct 14 - Oct 15
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Our top choices for Deal Island hotels

A person in a canoe on a calm body of water with grassy banks and trees in the background.
A covered porch with wicker furniture, a small table, and a view of a green landscape and water.
A waterfront dock with a pier, a white building, and a clear sky.
A river with a dock, a sailboat, and a motorboat. There are buildings and trees in the background.

1. The Whitehaven Hotel

The Whitehaven Hotel
Quantico
United States
Tracy
CA $189
CA $211 total
includes taxes & fees
Nov 3 - Nov 4
The Whitehaven Hotel
A hotel room with a large bathtub, a double bed, a desk, and a chair.
A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple balconies.
A dining area with a wooden table and chairs, a kitchen area with a refrigerator and coffee maker, and a view through the glass doors.
A spacious hotel lobby with a reception desk, a large window with curtains, and a tiled floor.

2. Econo Lodge Princess Anne

Econo Lodge Princess Anne
Princess Anne
United States
Sidney R
CA $101
CA $112 total
includes taxes & fees
Nov 3 - Nov 4
Econo Lodge Princess Anne
A hotel with a swimming pool, outdoor seating, and a view of the water.
A spacious room with light blue walls, wooden flooring, and a reception desk with a mirror. There are two tables with chairs and a water dispenser.
A hotel room with a bed, an air conditioning unit, and a sliding glass door leading to a balcony with a pool and greenery.
A hotel room with two beds, a TV, a desk, and a lamp.

3. Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina
Crisfield
United States
Casey
CA $126
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Rodeway Inn at Somers Cove Marina
A yellow motel with a sign reading "Best UFO" and a car parked in front.
A hotel room with a large bed, a bedside table, a desk, a chair, a mirror, and a bathroom with a sink and toilet.
A two-story motel with a yellow facade, balconies, and a parking lot.
A hotel room with two single beds, a desk, a chair, a nightstand with a phone, and a lamp.

4. Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne
Princess Anne
United States
Leonard
CA $97
CA $107 total
includes taxes & fees
Oct 16 - Oct 17
Americas Best Value Inn Princess Anne
Terrace/patio
A hotel room with a grey sofa, a small ottoman, a bed, a nightstand with a lamp, a wall-mounted painting, and a mirror with a pink frame.
Pool
A self-service breakfast station with a coffee machine, yogurt dispensers, and a variety of food items.

5. Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland
Fruitland
United States
JoAnn
CA $155
CA $174 total
includes taxes & fees
Nov 9 - Nov 10
Home2 Suites By Hilton Salisbury Fruitland
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.
A hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.

6. Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
United States
Laura
CA $157
CA $175 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Salisbury/Fruitland
A modern lobby with a reception desk, seating area, and artwork on the walls.
Exterior
A hotel room with a bed, a sofa, a TV, a desk, and a large window.
A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.

7. Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
United States
alexis
CA $161
CA $181 total
includes taxes & fees
Nov 10 - Nov 11
Best Western Plus Pocomoke City
A large, historic house with multiple chimneys, a spacious lawn, and a sunset sky.
A swimming pool with a fountain, surrounded by lounge chairs and a table, with a lake and trees in the background.
A modern kitchen with white cabinets, granite countertops, a stainless steel refrigerator, a built-in oven, a dishwasher, and a coffee maker.
A wooden deck with a table and chairs, overlooking a lake with trees and a grassy area.

8. Kingsbay Mansion & Vacation Houses

Kingsbay Mansion & Vacation Houses
Marion Station
United States
Tracy
CA $557
CA $618 total
includes taxes & fees
Oct 26 - Oct 27
Kingsbay Mansion & Vacation Houses
View all properties

Hotels recommended for families in Deal Island

A sandy beach with footprints, a pier in the distance, and a clear sky.
A dining area with a wooden table and benches, a small kitchen counter with decorative items, and a view through a window with curtains.
A hallway with a framed artwork of a bird, a wooden entertainment unit with a TV, and a dining area with a bar stool.
A living room with a gray sectional sofa, wooden flooring, a hallway leading to a door, and a shelf with decorative items.

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
CA $156
CA $354 total
includes taxes & fees
Oct 21 - Oct 22
Tangier Escape, great place get away from it all on Deal Island, MD.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.
A covered outdoor area with a table and chairs, a grill, and a view of the surrounding landscape.
Two people fishing on a sandy beach with a sunset in the background.
A bedroom with a bed, a desk, a chair, a wardrobe, a ceiling fan, and a window.

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
CA $198
CA $366 total
includes taxes & fees
Oct 18 - Oct 19
Deal Island Bay Cottage
A hotel with a swimming pool, outdoor seating, and a view of the water.
A spacious room with light blue walls, wooden flooring, and a reception desk with a mirror. There are two tables with chairs and a water dispenser.
A hotel room with a bed, an air conditioning unit, and a sliding glass door leading to a balcony with a pool and greenery.
A hotel room with two beds, a TV, a desk, and a lamp.

Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina
Crisfield
CA $126
CA $143 total
includes taxes & fees
Nov 12 - Nov 13
Rodeway Inn at Somers Cove Marina
A person in a canoe on a calm body of water with grassy banks and trees in the background.
A covered porch with wicker furniture, a small table, and a view of a green landscape and water.
A waterfront dock with a pier, a white building, and a clear sky.
A river with a dock, a sailboat, and a motorboat. There are buildings and trees in the background.

The Whitehaven Hotel

The Whitehaven Hotel
Quantico
CA $189
CA $211 total
includes taxes & fees
Nov 3 - Nov 4
The Whitehaven Hotel
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.
A living room with a brown leather couch, wooden walls, a television on a wooden cabinet, a door with blinds, and a framed picture on the wall.
A bedroom with a bed, a nightstand, a lamp, a painting on the wall, and a window with curtains.
A kitchen with wooden cabinets, a dining table with chairs, a refrigerator, a microwave, and a sink.

Cottage near the Bay

Cottage near the Bay
Crisfield
CA $115
CA $265 total
includes taxes & fees
Oct 19 - Oct 20
Cottage near the Bay
A modern indoor pool area with wooden beams, a pool, and seating arrangements.
A spacious lobby with a mix of seating options, including sofas and chairs, and a bar area with stools.
A modern hotel room with a kitchenette, a large mirror, a flat-screen TV, and a sofa.
A hotel room with two beds, a desk, a TV, a chair, and a large window with curtains.

Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland
Fruitland
CA $157
CA $175 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Salisbury/Fruitland
A modern lobby with a reception desk, seating area, and artwork on the walls.
Exterior
A hotel room with a bed, a sofa, a TV, a desk, and a large window.
A hotel room with a large bed, bedside lamps, a nightstand, a window with blinds, and a wall-mounted abstract painting.

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
Pocomoke City
CA $161
CA $181 total
includes taxes & fees
Nov 10 - Nov 11
Best Western Plus Pocomoke City
A marina at sunset with boats docked and buildings in the background.
A wooden deck with white railings, a door with a wreath, and two wicker chairs.
A compact, modern bathroom with a sink, mirror, and two stacked washing machines.
A two-story house with a porch, a driveway, and a golf cart parked in front.

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
CA $284
CA $476 total
includes taxes & fees
Oct 16 - Oct 17
Come out and enjoy Autumn at the HH Ranch on Smith Island.
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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.
See properties

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.
See properties

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.
See properties

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

The Whitehaven Hotel

The Whitehaven Hotel

10/10 Excellent
"The hotel is a gem, located along the Wicomico River. It's elegant and charming and quiet. What makes it even more special are the hosts Brent and Stephanie. Their breakfasts are superb. They are there to help and make your stay pleasant, but are not intrusive. You feel like being in a home away from home. Loved out stay."
Theodore 4-night trip
Posted 9 hours ago
The Whitehaven Hotel
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Bed was comfortable, everything was clean, staff are very helpful and nice."
Rachel 1-night trip
Posted 22 hours ago
Best Western Plus Pocomoke City
Econo Lodge Princess Anne

Econo Lodge Princess Anne

10/10 Excellent
"Everything was nice"
Sidney R 1-night trip
Posted 3 days ago
Econo Lodge Princess Anne
Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

10/10 Excellent
"Staff was great and clean rooms"
Leonard 5-night trip
Posted 2 weeks ago
Americas Best Value Inn Princess Anne
Deal Island Bay Cottage

Deal Island Bay Cottage

10/10 Excellent
"nice clean place had everything we needed and the host was very responsive to any questions I had"
Brenda B. 7-night trip
Posted 3 weeks ago
Deal Island Bay Cottage
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

8/10 Good
"The house had a nice, rustic vibe, which I like. The rooms were as pictured and spacious. The beach and a boat launch were five minutes away, and the marsh and bay was beautiful. On the way in to the island we caught a late night thunderstorm which was quite impressive. The geography of Deal Island and the Chesapeake Bay meant we could see the lightning but not really be in the storm. If you are looking for a comfortable and quiet place to stay on the Delmarva peninsula, this place is great. If you want to be close to what's going on, not so much. The closest gas station was 16 miles away, as was the closest grocery store. Just something to be aware of. However, within about an hour you have the shops and restaurants of Salisbury, MD, the beautiful Chincoteague National Park and the Wallops NASA Rocket Launch center. And Norfolk, VA is only about two and a half hours via the Chesapeake Bay bridge and tunnel. This house was a great place to relax and a great staging area for day trips and paddling excursions. It has a fair kitchen, with basic kitchen equipment. Feeding our family of seven took a bit of creative adjustment. I'm a bit of a foodie and used to a well equipped kitchen and a well stocked pantry. This kitchen was functional and adequate. It did have a dishwasher and a Belgian waffle maker, though, both of which were used and appreciated. And I didn't think I would like it much, but the outdoor (enclosed) shower was more popular than the indoor one. Recommended."
Jon K. 14-night trip
Posted 1 month ago
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

10/10 Excellent
"The place was fantastic. It had everything we needed and then some. Would love to go back!"
Michelle J. 3-night trip
Posted 1 month ago
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!

10/10 Excellent
"We had a great time in this beautiful home. The views are truly unmatched!"
Kelly G. 3-night trip
Posted 1 month ago
Waterfront Maryland Retreat w/ Dock & Bay View!
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

10/10 Excellent
"Great place to get away. Clean, quiet, host was attentive. Had a great time."
Dan M. 4-night trip
Posted 2 months ago
Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly

More cheap stays in Deal Island

Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

30359 Mt. Vernon Road Princess Anne MD
CA $97
CA $107 total
Oct 16 - Oct 17
includes taxes & fees
7/10 Good! (80 reviews)
Americas Best Value Inn Princess Anne
Econo Lodge Princess Anne

Econo Lodge Princess Anne

10936 Market Lane US 13 Princess Anne MD
CA $101
CA $112 total
Nov 3 - Nov 4
includes taxes & fees
6.6/10 (722 reviews)
Econo Lodge Princess Anne
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

700 Norris Harbor Dr Crisfield MD
CA $126
CA $143 total
Nov 12 - Nov 13
includes taxes & fees
Rodeway Inn at Somers Cove Marina
Hampton Inn & Suites Salisbury/Fruitland

Hampton Inn & Suites Salisbury/Fruitland

304 Prosperity Lane Fruitland MD
CA $157
CA $175 total
Nov 1 - Nov 2
includes taxes & fees
Hampton Inn & Suites Salisbury/Fruitland
Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

125 Newtowne Blvd Pocomoke City MD
CA $161
CA $181 total
Nov 10 - Nov 11
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Best Western Plus Pocomoke City

Hotels in Deal Island with star rating

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 CA $107 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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