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Kingston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 CA $115
CA $264 total
includes taxes & fees
Sep 30 - Oct 1
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 CA $156
CA $351 total
includes taxes & fees
Oct 19 - Oct 20
Tangier Escape, great place get away from it all on Deal Island, MD.
A kitchen with a farmhouse sign, a clock, and a refrigerator.

3. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is CA $196
CA $380 total
includes taxes & fees
Sep 30 - Oct 1
Cozy Barn Loft: Country Views & Central to Beaches
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

4. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 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 CA $198
CA $366 total
includes taxes & fees
Oct 1 - Oct 2
Deal Island Bay Cottage
A sunroom with wicker furniture, large windows, and a view of the water.

5. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 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 CA $223
CA $636 total
includes taxes & fees
Sep 30 - Oct 1
The purple door at the bay.
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

6. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"Overall nice stay!"
United States
Becky S.
The price is CA $193
CA $711 total
includes taxes & fees
Oct 1 - Oct 2
Bayfront Modern Retreat • Dock, Kayaks, Views
A marina at sunset with boats docked and buildings in the background.

7. 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 CA $283
CA $461 total
includes taxes & fees
Oct 26 - Oct 27
Come out and enjoy Autumn at the HH Ranch on Smith Island.
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

Americas Best Value Inn Princess Anne

Americas Best Value Inn Princess Anne

10/10 Excellent
"Staff was great and clean rooms"
Leonard 5-night trip
Posted 1 hour ago
Americas Best Value Inn Princess Anne

Find out more about Kingston

Everything you need to know about Kingston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kingston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kingston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kingston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kingston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kingston vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kingston vacation rentals we have selected for you start as low as CA $264 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kingston rentals

At Expedia, we put the best Kingston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kingston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kingston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kingston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.