Holiday Rentals in Kingston

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kingston holiday rentals

9.8 out of 10, Exceptional, (61 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
The price is €391
includes taxes & fees
11 Mar - 12 Mar
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is €164
includes taxes & fees
12 Mar - 13 Mar
Cottage near the Bay
10.0 out of 10, Exceptional, (19 reviews)
"Was wonderfully comfortable and clean. Would definitely recommend. "
United States
Joy D.
The price is €229
includes taxes & fees
20 Mar - 21 Mar
Cozy Barn Loft: Country Views & Central to Beaches
3.0 star property
The price is €479
includes taxes & fees
17 Mar - 18 Mar
1 Mi to Resort Marina! Greenbackville Retreat

Cottage in Deal Island

Deal Island Bay Cottage
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 €220
includes taxes & fees
11 Mar - 12 Mar
Deal Island Bay Cottage

Holiday Home in Captain's Cove

The purple door at the bay.
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 €384
includes taxes & fees
11 Mar - 12 Mar
The purple door at the bay.

Holiday Home in Captain's Cove

1 Mi to Resort Marina! Greenbackville Retreat
The price is €483
includes taxes & fees
16 Mar - 17 Mar
1 Mi to Resort Marina! Greenbackville Retreat

Holiday Home in Smith Island

Historic home on Smith Island w/ dock!
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
The price is €264
includes taxes & fees
31 Mar - 1 Apr
Historic home on Smith Island w/ dock!
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 €304
includes taxes & fees
1 Apr - 2 Apr
Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
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 Kingston Hotel Reviews

Find out more about Kingston

Everything you need to know about Kingston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kingston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kingston holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kingston holiday rentals we have selected for you start as low as €164 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 holiday 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 holiday.

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 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?

Sun Rayes | Canal Dock, Elevator, Game Room + Pet Friendly Captain's Cove Retreat: This holiday home rental outside of Kingston is located on the waterfront, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room 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 Chesapeake Forest - Dunn Swamp Complex. Coventry Parish Ruins and Pocomoke Fair Grounds 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.