Kingston Holiday Rentals

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Holiday Rentals in Kingston

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (158)
"An amazing experience with amazing people. We made this annual visit and every year it gets better and better. We will definitely be coming back. Thank you so much to the hosts for having us and best wishes."
Cabin at Holdens Creek on Eastern Shore of VA

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is AU$338
includes taxes & fees
26 Nov - 27 Nov
Deal Island Bay Cottage

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (42)
"Yurt-ques unique house! Nicely decorated and fully stocked. Perfect place to fish and crab off the dock. Furnishing was perfect inside and out! We didn’t leverage but what a cool canoe! Love the patio lights which allowed us to fish/crab at night. If you’re looking for a quiet place to relax, this is the perfect place for you. One side note, you should plan to get food for the week unless you want to go into town (30 mins) for food which we did every day. Wasn’t a big deal for us since most of...
The price is AU$599
includes taxes & fees
25 Nov - 26 Nov
Stunning waterfront panoramic view getaway house

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (6)
"The location, accommodations and the quality of the amenities were stellar. The best vacation we have spent as a family! The whole experience was best in class!"
Creek House - Waterfront Oasis on Holden's Creek

Cottage near the Bay

8.6 out of 10, Excellent, (27)
"Attended a family wedding in the area. Perfect distance "
The price is AU$310
includes taxes & fees
25 Nov - 26 Nov
Cottage near the Bay

Waterfront 3 bedroom condo. Fall and oysters are here!

10.0 out of 10, Exceptional, (36)
"We soent three nights. Sunsets were amazing. Slept well and the kitchen was easy to cook in."
Waterfront 3 bedroom condo. Fall and oysters are here!

Hidden Gem! Clean & Cozy and Family Friendly!

9.6 out of 10, Exceptional, (54)
"Overall our stay here was great. The house was clean, and the furniture and beds were comfortable. The rooms are spacious. The only negatives for us were the very low water pressure in the shower, and having to park under a pine tree that dropped needles and sap all over our cars. All my interactions with the owner were great. "
Hidden Gem! Clean & Cozy and Family Friendly!

Waterfront Marion Station Retreat w/ Private Dock!

8.0 out of 10, Very good, (3)
"The house was beautiful and was stocked with everything you could need for a perfect stay. Sunsets were phenomenal and it was very peaceful and relaxing. We hope to come back next year!! Highly recommend "
Waterfront Marion Station Retreat w/ Private Dock!

Beautiful Bayfront with Sanctuary Private Beach

9.0 out of 10, Wonderful, (17)
"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

The purple door at the bay.

9.4 out of 10, Exceptional, (39)
"We enjoyed our stay at the Purple Door. The views were spectacular and we enjoyed sitting on the deck. My husband taught my daughter to fish and she loved the dock area. We did use the amenities at Captain’s Cove and drove out to Assateague Island to see the horses. The location is tucked away from major attractions but we got used to the drive after the first day. The neighbors were friendly. Enjoyed our stay !"
The price is AU$932
includes taxes & fees
25 Nov - 26 Nov
The purple door at the bay.

Breathe the Bay - Waterfront w/ Dock, Pool & Golf!

9.4 out of 10, Exceptional, (6)
"Great place , I bit isolated but doable. Everyone very friendly, amenities setup is a bit of a pain in the ass . "
Breathe the Bay - Waterfront w/ Dock, Pool & Golf!

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (14)
"Loft was spotless, and had everything we needed. "
The price is AU$442
includes taxes & fees
25 Nov - 26 Nov
Cozy Barn Loft: Country Views & Central to Beaches

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (36)
"The location was perfect, our host was extremely responsive and helpful. Chris gave us tips and set us up with the ferry Captain. Even though the large restaurant was closed there are 2 chefs that prepare wonderful meals! The srore/museum was ooen go meet the sweet manager! Thank you Chris for a wonderful family vacation!"
Historic home on Smith Island w/ dock!

Casa Del Canal is a fabulous Waterfront Vacation Home only minutes from Chincote

8.8 out of 10, Excellent, (49)
"We thoroughly enjoyed our stay at captains cove. The house was perfect for our needs in a beautiful location. Would recommend. It would be helpful though if there was a ladder to get in and out of the bay. Some of the steps in the front of the house should be fixed also. This did not take away from our stay."
Casa Del Canal is a fabulous Waterfront Vacation Home only minutes from Chincote

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

10.0 out of 10, Exceptional, (22)
"Great place to stay!!!"
Kick back and relax at “Knot Stressed” in total comfort.

Diving Duck - Waterfront home w Hot tub & Boat dock & King Bed

8.8 out of 10, Excellent, (24)
"Enjoyed everything about this home. Lots of room and couldn't ask for better stock."
Diving Duck - Waterfront home w Hot tub & Boat dock & King Bed

Come, sit back and relax at the "Catch of the Bay"

10.0 out of 10, Exceptional, (5)
"This was a great place to stay and I highly recommend it to anyone. We were really impressed with all the "extras" that were included. We didn't need to go out any buy anything unexpected."
Come, sit back and relax at the "Catch of the Bay"

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"Staying at the Quaint Island Getaway is always a pleasure! Sarah is an accessible host, the property is cozy and clean. My party loved the new firepit."
Quaint Island Getaway

Poseidon's Oasis - Pet friendly, Screened porch!

Poseidon's Oasis - Pet friendly, Screened porch!

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

8.6 out of 10, Excellent, (46)
"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!
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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Other types of properties in Kingston you may be interested in

Hampton Inn & Suites Salisbury/Fruitland

2.5 star property
9.2 out of 10, Wonderful, (1032)
"Great hotel. Clean rooms. Excellent and accommodating staff. "
The price is AU$225
includes taxes & fees
26 Nov - 27 Nov
Hampton Inn & Suites Salisbury/Fruitland

Holiday Inn Express Pocomoke, an IHG Hotel

2.5 star property
8.4 out of 10, Very good, (735)
"Room was updated. Staff friendly and responsive. Great location. "
The price is AU$169
includes taxes & fees
26 Nov - 27 Nov
Holiday Inn Express Pocomoke, an IHG Hotel

Econo Lodge Princess Anne

2.0 star property
6.6 out of 10, (578)
"Nothing"
The price is AU$145
includes taxes & fees
25 Nov - 26 Nov
Econo Lodge Princess Anne
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Stunning waterfront panoramic view getaway house: This holiday home rental outside of Kingston is located next to a golf course, and has an outdoor pool, a balcony 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. 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 Pocomoke River State Park. Pocomoke Fair Grounds and University of Maryland Eastern Shore 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.