Kingston Vacation Rentals

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Our top choices for Kingston vacation rentals

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $194
CA $360 total
includes taxes & fees
Apr 6 - Apr 7
Deal Island Bay Cottage

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
Captain's Cove
The price is CA $150
CA $488 total
includes taxes & fees
Apr 9 - Apr 10
1 Mi to Resort Marina! Greenbackville Retreat

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is CA $219
CA $619 total
includes taxes & fees
Apr 15 - Apr 16
The purple door at the bay.

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
Historic home on Smith Island w/ dock!

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is CA $112
CA $260 total
includes taxes & fees
Apr 15 - Apr 16
Cottage near the Bay

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
The price is CA $312
CA $495 total
includes taxes & fees
Apr 3 - Apr 4
Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
Captain's Cove
The price is CA $133
CA $495 total
includes taxes & fees
Apr 9 - Apr 10
1 Mi to Resort Marina! Greenbackville Retreat

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, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is CA $153
CA $343 total
includes taxes & fees
Apr 29 - Apr 30
Tangier Escape, great place get away from it all on Deal Island, MD.
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 Kingston Hotel Reviews

Find out more about Kingston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Kingston. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Kingston?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Kingston, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Kingston has to offer?

Porter's Barn | Luxury Creekfront Retreat w/ Resort Perks, Kayaks & Secluded Waterfront Escape: This vacation home near Kingston is located on the waterfront and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Kingston?

While exploring the area, visit family-friendly sights like Delmarva Discovery Center, or get outside and enjoy nature at Chesapeake Forest - Dunn Swamp Complex. Great Hope Golf Course and Coventry Parish Ruins are a couple of places you'll find in the larger area.

What’s a vacation rental in Kingston like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Kingston. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of 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 an attractive option for a family trip or a small group gathering.