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Top Holiday Rentals in Kingston

Our top choices for Kingston holiday rentals

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is £342
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (172)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
Cabin at Holdens Creek on Eastern Shore of VA

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"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!

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is £143
includes taxes & fees
24 Aug - 25 Aug
Cottage near the Bay

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is £359
includes taxes & fees
1 Sept - 2 Sept
Stunning waterfront panoramic view getaway house

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

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

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

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (21)
"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

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (19)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

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.

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

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

10.0 out of 10, Exceptional, (18)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

Charming bungalow on the bay behind Chincoteague

6.0 out of 10, (1)
"Overall, this was a pleasant place to stay for the evening. The community was extremely cute, and we enjoyed walking our dogs around the property. There were a few issues that could easily be fixed. The bathrooms that were closest to the property were locked, and we had trouble finding ones that were open. (We arrived after dark.) Also, because we came in after dark, it was difficult to get into the house. There weren't any lights, and the community is very dark. Adding some sort of small light...
Charming bungalow on the bay behind Chincoteague

Your Song - Gorgeous Waterfront in Captain's Cove!

10.0 out of 10, Exceptional, (1)
"Our stay at "Our Song" was amazing, the house is PERFECT! Just as described, right on the water! We had the best time and would DEF stay here again!"
Your Song - Gorgeous Waterfront in Captain's Cove!

Off Duty - Pet Friendly, Waterfront!

9.6 out of 10, Exceptional, (5)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Quiet community, pet friendly."
Off Duty - Pet Friendly, Waterfront!

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"The house is absolutely beautiful and the view is spectacular ! If by chance you forget to bring something with you dont worry they have it all right down to the lotion. The neighbors are great too ! Loved our stay."
Waterfront Maryland Retreat w/ Dock & Bay View!

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

2.0 star property
10.0 out of 10, Exceptional, (4)
"Had an amazing time here very piecefull and beautiful "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River

Creek House - Waterfront Oasis on Holden's Creek

9.6 out of 10, Exceptional, (10)
"Beautiful Home, Great Location, Great Communication with Vrbo and the owner. All appliances were up to date and easy to use. "
Creek House - Waterfront Oasis on Holden's Creek

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

10.0 out of 10, Exceptional, (32)
"Beautiful panorama!"
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit
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

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?

The purple door at the bay.: This holiday home rental outside of Kingston is located on the waterfront, and has an outdoor pool, a balcony and air conditioning 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.

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.