A beach with several boats and people fishing.

Deal Island Vacation Rentals

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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 Deal Island vacation rentals

A sandy beach with footprints, a pier in the distance, and a clear sky.

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 ￥17,414
￥38,931 total
includes taxes & fees
Oct 19 - Oct 20
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.

2. 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.
The price is ￥22,084
￥40,693 total
includes taxes & fees
Oct 14 - Oct 15
Deal Island Bay Cottage
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.
The price is ￥12,823
￥29,534 total
includes taxes & fees
Oct 15 - Oct 16
Cottage near the Bay
A marina at sunset with boats docked and buildings in the background.

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, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is ￥31,662
￥52,776 total
includes taxes & fees
Oct 21 - Oct 22
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A row of white houses by a lake with American flags.

5. 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.
The price is ￥36,411
￥61,753 total
includes taxes & fees
Oct 15 - Oct 16
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
A house with a large lawn and a dock extending into a calm lake.

6. 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 ￥43,535
￥52,859 total
includes taxes & fees
Oct 15 - Oct 16
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A house with a large lawn and a dock extending into a calm lake.

7. 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 ￥39,182
￥47,574 total
includes taxes & fees
Oct 14 - Oct 15
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A single-story house with a front porch, a door, and a mailbox.

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 ￥28,397
￥62,724 total
includes taxes & fees
Nov 2 - Nov 3
Salisbury Hideaway
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

9. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is ￥24,696
￥58,565 total
includes taxes & fees
Nov 3 - Nov 4
Salisbury Cottage
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

The Whitehaven Hotel

The Whitehaven Hotel

10/10 Excellent
"I was so delightfully impressed with this place. It’s just an adorable old mansion. I’d say converted into bed breakfast. The innkeepers are an adorable couple. Place is right on the water. It’s gorgeous. I stayed to visit my son at college. It was a tiny bit out of the way but so worth it. Pretty area. I’ll be back no doubt."
Stephen 1-night trip
Posted 1 day ago
The Whitehaven Hotel

Find out more about Deal Island

Search for holiday rentals in Deal Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Deal Island using one of the methods below:

  • View our selection of featured holiday rentals in Deal Island
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Look no further and take a look at our great range of rental properties in Deal Island!

Frequently asked questions

Can I find a vacation rental in Deal Island?

Yes, we offer vacation rentals near well known sights in Deal Island, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals that Deal Island has to offer?

Beautiful Bayfront with Sanctuary Private Beach : This vacation 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 the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Deal Island?

With 8 Expedia vacation rentals, you're sure 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 vacation rental in Deal Island like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Deal Island. Vacation rentals feature extras such as patios, hot tubs, and fire pits so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.