A beach with several boats and people fishing.

Deal Island Holiday Rentals

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Our top choices for Deal Island holiday rentals

1. 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.
The price is NZ$438
includes taxes & fees
11 Nov - 12 Nov
Tangier Escape, great place get away from it all on Deal Island, MD.

2. Deal Island Bay Cabin

Deal Island Bay Cabin
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is NZ$419
includes taxes & fees
11 Nov - 12 Nov
Deal Island Bay Cabin

3. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 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.
The price is NZ$316
includes taxes & fees
22 Nov - 23 Nov
Cottage near the Bay

4. 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.
The price is NZ$541
includes taxes & fees
15 Nov - 16 Nov
Come out and enjoy Autumn at the HH Ranch on Smith Island.

5. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is NZ$555
includes taxes & fees
11 Nov - 12 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

6. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is NZ$500
includes taxes & fees
17 Nov - 18 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

7. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"The property has cute and cozy curb appeal. The interior was attractive and very clean. The location was excellent for our planned events. Host, Ryan, easily accommodated our needs and we plan to check for availability in the future. Thanks Ryan!"
United States
Star R.
The price is NZ$614
includes taxes & fees
11 Nov - 12 Nov
Salisbury Cottage

8. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is NZ$557
includes taxes & fees
29 Nov - 30 Nov
Salisbury Hideaway
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 Deal Island Hotel Reviews

Find out more about Deal Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Deal Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Deal Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Deal Island. Seeing all the best attractions is bound to make you fall in love with Deal Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Deal Island short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Deal Island?

Yes, there are holiday rentals close to the most popular sights in Deal Island, or you can select a more secluded option if you're looking for a relaxing stay. Deal Island is known for its beaches and seafood restaurants. Make sure you have time to check out the bars while you're in the area.

What are some of the best holiday rentals that Deal Island has to offer?

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

How many holiday rentals will I find in Deal Island?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Deal Island stay.

What’s there to see and do in Deal Island?

Crab Island and Rock Island are a couple of lovely local spots to get outside and enjoy nature. Franks Island and Shark Fin Shoal are other places to visit while you're in town.

What’s a holiday rental in Deal Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Deal Island. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip or a small group gathering.