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Kingston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Kingston vacation rentals

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

1. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is ￥12,813
￥29,510 total
includes taxes & fees
Oct 12 - Oct 13
Cottage near the Bay
A sandy beach with footprints, a pier in the distance, and a clear sky.

2. 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 ￥17,400
￥38,900 total
includes taxes & fees
Oct 14 - Oct 15
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.

3. 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 ￥22,066
￥40,660 total
includes taxes & fees
Oct 12 - Oct 13
Deal Island Bay Cottage
A sunroom with wicker furniture, large windows, and a view of the water.

4. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
The price is ￥24,913
￥71,272 total
includes taxes & fees
Oct 11 - Oct 12
The purple door at the bay.
A row of white houses by a lake with American flags.

5. Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
Smith Island
10.0 out of 10, Exceptional, (2 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 ￥30,371
￥54,661 total
includes taxes & fees
Oct 13 - Oct 14
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
A marina at sunset with boats docked and buildings in the background.

6. 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 ￥31,582
￥51,766 total
includes taxes & fees
Oct 17 - Oct 18
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

7. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (70 reviews)
"Overall nice stay!"
United States
Becky S.
The price is ￥21,987
￥80,431 total
includes taxes & fees
Nov 3 - Nov 4
Bayfront Modern Retreat • Dock, Kayaks, Views
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

Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

10/10 Excellent
"It was a very comfortable stay. The lobby is nice and bring with ample seating for eating, the staff is very nice, helpful and friendly, the suites are comfy, a nice size and very spacious. Will definitely be staying there again next year."
Dwayne 4-night trip
Posted 1 day ago
Home2 Suites By Hilton Salisbury Fruitland

Find out more about Kingston

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

  • View our selection of featured holiday rentals in Kingston
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  • Enter your travel dates to view the best deals on holiday rentals in Kingston while they last

Look no further and take a look at our great range of rental properties in Kingston!

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?

Beautiful Bayfront with Sanctuary Private Beach : This vacation home near Kingston 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.

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 Cypress Park. Pocomoke City Hall and Manokin Park 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.