Kingston Holiday Rentals

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec

Holiday Rentals in Kingston

Cabin at Holdens Creek on Eastern Shore of VA
Interior

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (180)
"Thank you for your hospitality!! Your rental property is absolutely amazing! We love cabins and yours made us feel so at home. We are looking forward to visit again!"
Cabin at Holdens Creek on Eastern Shore of VA
Cottage near the Bay
Dining

Cottage near the Bay

8.8 out of 10, Excellent, (46)
"great, peaceful "
The price is AU$286
includes taxes & fees
1 Oct - 2 Oct
Cottage near the Bay
The purple door at the bay.
Terrace/patio

The purple door at the bay.

9.2 out of 10, Wonderful, (52)
"Had a great time with my family enjoyed the rental property very nice location and view every morning was fantastic"
The price is AU$682
includes taxes & fees
22 Sept - 23 Sept
The purple door at the bay.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Outdoor dining

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
Anchor's Away - Waterfront, Pet Friendly, Pools!
Property grounds

Anchor's Away - Waterfront, Pet Friendly, Pools!

10.0 out of 10, Exceptional, (2)
"The home was lovely, very nicely decorated, beds were very comfortable. "
Anchor's Away - Waterfront, Pet Friendly, Pools!
Beautiful Bayfront with Sanctuary Private Beach
Property grounds

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (24)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach
Stunning waterfront panoramic view getaway house
Property grounds

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (54)
"The Property was very well-maintained and accommodating, with most everything you could need. This made the stay much simpler and more enjoyable. The dock and kayaks were a great addition to the fun. "
The price is AU$768
includes taxes & fees
1 Oct - 2 Oct
Stunning waterfront panoramic view getaway house
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit
Exterior

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

10.0 out of 10, Exceptional, (33)
"Beautiful, private, relaxing! We loved our stay! The only thing and reason we say 4 stars is we would have loved privacy curtains on the large and small windows. "
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
Smart TV, fireplace, ping pong, books

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

9.8 out of 10, Exceptional, (13)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
The price is AU$527
includes taxes & fees
22 Sept - 23 Sept
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Exterior

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (18)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK
Robert's Retreat - Brand new home w/ gorgeous water views!
Exterior

Robert's Retreat - Brand new home w/ gorgeous water views!

8.0 out of 10, Very good, (2)
"Robert’s retreat was new and an awesome place to stay. We weren’t thrilled with management company, we extended our stay and they locked us out and did not answer phone or emails for the whole entire week. "
Robert's Retreat - Brand new home w/ gorgeous water views!
Waterfront Historic Gem w/ Kayaks & Fire Pit
Fridge, microwave, oven, stovetop

Waterfront Historic Gem w/ Kayaks & Fire Pit

8.6 out of 10, Excellent, (4)
"Great house. Clean. Had everything we needed."
Waterfront Historic Gem w/ Kayaks & Fire Pit
Beautiful, Waterfront, Luxury
Terrace/patio

Beautiful, Waterfront, Luxury

10.0 out of 10, Exceptional, (4)
"Great place for a weekend away - house was beautiful and hosts were always quick to answer"
Beautiful, Waterfront, Luxury
Sun Rayes - Pet friendly; Waterfront w/ Boat dock!
Exterior

Sun Rayes - Pet friendly; Waterfront w/ Boat dock!

8.6 out of 10, Excellent, (48)
"This was our 2nd time staying in this home. It's so spacious and has amazing views. We loved that we were able to bring our dog, as well."
Sun Rayes - Pet friendly; Waterfront w/ Boat dock!
Walk to Main St: Condo w/ Pool Access in Crisfield
Marina

Walk to Main St: Condo w/ Pool Access in Crisfield

9.0 out of 10, Wonderful, (6)
"Great location. Needed to be cleaned a bit better. Lots of dust. Fridge and the utensils needed to be cleaned….. One small tv in the living room was not enough. Needed a tv in the bedroom. Good overall. "
Walk to Main St: Condo w/ Pool Access in Crisfield
Kick back and relax at “Knot Stressed” in total comfort.
Interior

Kick back and relax at “Knot Stressed” in total comfort.

10.0 out of 10, Exceptional, (30)
"We have family in the area and this was our second time staying at Knot Stressed while we visited them. It's the perfect size for our family of 4. It's clean, quiet, and equipped with all the necessities. We loved walking around the neighborhood and out to the water. We'll stay here every time we come to visit."
Kick back and relax at “Knot Stressed” in total comfort.
Coastal Crab - Waterfront with incredible Amenities.
Indoor pool, a heated pool

Coastal Crab - Waterfront with incredible Amenities.

10.0 out of 10, Exceptional, (3)
"Very nice place to stay!! Description of house and everything included is accurate and on point. Had a fantastic vacation! Will be staying there again next year. "
Coastal Crab - Waterfront with incredible Amenities.
Par-Lon - Private Raised Waterfront Home on the Pocomoke River
Outdoor dining

Par-Lon - Private Raised Waterfront Home on the Pocomoke River

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was beautiful and our stay was great. Looking forward to future visits. "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River
Creek House - Waterfront Oasis on Holden's Creek
Dining

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (12)
"This property was lovely in every respect—its site on Holdens Creek, its living and sleeping spaces, and its proximity to Assateague where we went for a day. We highly recommend it for a family group. "
Creek House - Waterfront Oasis on Holden's Creek
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

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Staff were very friendly and attentive. Hotel is beautifully appointed and very clean. The room was very spacious. The only thing I did not like was that the sink was on the outside of the bathroom. That meant that everyone had to touch the door handle before they washed their hands. And there was no privacy for other bathroom activities that require a sink and/or mirror. And there were no counters, hooks or shelves for personal items inside the bathroom. "
Jacqueline 2-night trip
Posted 5 days ago
Best Western Plus Pocomoke City

Find out more about Kingston

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, 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 favourite 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 depend 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 AU$286 per night. Entering your travel dates in the search wizard might find you 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?

Historic home on Smith Island w/ dock!: This holiday home rental outside of Kingston is located on the waterfront, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Fair Grounds and Pocomoke City Hall 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.