Chance Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Chance

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"The house is absolutely beautiful and the view is spectacular ! If by chance you forget to bring something with you dont worry they have it all right down to the lotion. The neighbors are great too ! Loved our stay."
Waterfront Maryland Retreat w/ Dock & Bay View!

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
The price is CA $219
CA $381 total
includes taxes & fees
Sep 2 - Sep 3
Deal Island Bay Cottage

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

10.0 out of 10, Exceptional, (1)
"The home was beautiful, the owner was lovely, and the views were spectacular. If you like spending your days on the dock and your nights surrounded by a gorgeous colorful home this is the place for you! "
Reel Relaxation-Waterfront 3-bedroom house in Deal Island Historic District

Waterfront Maryland Retreat w/ Dock & Bay View!

3.0 star property
Waterfront Maryland Retreat w/ Dock & Bay View!

Cottage near the Bay

9.0 out of 10, Wonderful, (41)
"great, peaceful "
The price is CA $111
CA $258 total
includes taxes & fees
Aug 11 - Aug 12
Cottage near the Bay

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (75)
"We had a very nice stay and enjoyed the quiet environment and the amenities of the property. Lots of great area for walking. "
Waterfront Cottage in Beautiful Hoopers Island

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is CA $274
CA $430 total
includes taxes & fees
Aug 11 - Aug 12
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Hoopers Island Retreat

Hoopers Island Retreat

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (10)
"Very happy with this place, quiet, clean, all good. "
The Blackwater refuge country house on a quiet 12 acres

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (17)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Secluded waterfront getaway with hot tub,fire pit, and private dock.

10.0 out of 10, Exceptional, (8)
"This is such a lovely place for families to unwind and enjoy time together!"
Secluded waterfront getaway with hot tub,fire pit, and private dock.

Home in historic Whitehaven Village.

10.0 out of 10, Exceptional, (4)
"Great stay! Nice and relaxing and owner fast response with questions!"
Home in historic Whitehaven Village.

Historic Hoopersville Getaway on Chesapeake Bay!

9.8 out of 10, Exceptional, (12)
"I really can’t say enough about this place! The house has so much charm! The island is very quiet! Great place to just get away and spend quality time with your family! Can’t wait to go back!"
Historic Hoopersville Getaway on Chesapeake Bay!

The Schultz Estate

7.0 out of 10, Good, (21)
"Had a great stay! Beautiful location! House was clean roomy, overall had a great time! The only thing I would say is work on the doors closing. In restrooms."
The Schultz Estate

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10.0 out of 10, Exceptional, (48)
"The house was exactly how the pictures showed !Cute and cozy ,and clean ! Im a country girl and felt at home sitting on the porch,enjoying the breeze. The sound of the ocean was a bonus!! Quiet and peaceful. I enjoyed the beautiful sunrises and morning walk on the dock. Overall i enjoyed my stay appreciate the hospitality of the host and would booked again !! "
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Walk to Main St: Condo w/ Pool Access in Crisfield

8.6 out of 10, Excellent, (4)
"My stay at this Condo was great. Loved the view and had everything we needed. Very nice place to stay if you visit the Eastern Shore. Beds were very comfortable and really enjoyed the sunsets here. They also had a pool but I didn't use it we were busy each day. Thanks for the great week at your Condo highly recommend to stay here. I give it 5 stars"
Walk to Main St: Condo w/ Pool Access in Crisfield

Riverfront Gem w/ Fire Pit in Eden

10.0 out of 10, Exceptional, (1)
"We srayed at this property due to number of guests and proximity to the college. It was a great mix of old and new. This house was wonderfully appointed and everyone enjoyed their stay. The views were spectacular and we had everything we needed and more. It was unexpectedly remote, but once we got used to it, it was barely noticeable. We are even considering staying here again "
Riverfront Gem w/ Fire Pit in Eden
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chance Hotel Reviews

Frequently asked questions

Can I find vacation rentals in Chance?

Yes, you can find vacation rentals close to popular points of interest in Chance, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Chance has to offer?

Cottage near the Bay: This vacation home rental outside of Chance is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Chance?

Expedia has 3 vacation rentals for your stay in Chance.

What’s there to see and do in Chance?

While you're exploring the area, Shark Fin Shoal and Rock Island are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Sandy Island and Elliott Island.

What’s a vacation rental in Chance like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Chance. Vacation rentals feature amenities 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 clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.