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Kingston Holiday Rentals

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Our top choices for Kingston holiday rentals

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 NZ$332
includes taxes & fees
12 Oct - 13 Oct
Cottage near the Bay

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 NZ$424
includes taxes & fees
15 Oct - 16 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.

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 NZ$455
includes taxes & fees
8 Oct - 9 Oct
Deal Island Bay Cottage

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 NZ$776
includes taxes & fees
14 Oct - 15 Oct
The purple door at the bay.

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 NZ$608
includes taxes & fees
13 Oct - 14 Oct
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

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 NZ$560
includes taxes & fees
18 Oct - 19 Oct
Come out and enjoy Autumn at the HH Ranch on Smith Island.

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 NZ$861
includes taxes & fees
3 Nov - 4 Nov
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

Find out more about Kingston

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 Kingston 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 Kingston. 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 Kingston. 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 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 Kingston short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Kingston?

Yes, there are holiday rentals close to the most popular sights in Kingston, or you can select a more secluded option if you're looking for a relaxing stay.

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

Beautiful Bayfront with Sanctuary Private Beach : This holiday home rental outside of Kingston 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.

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 wider area.

What’s a holiday rental in Kingston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kingston. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find 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 small group gathering.