Located in Milton, this guesthouse is in the city centre and near the beach. Milton Historical Society and Milton Theater are cultural highlights, and some of the area's activities can be experienced at Dogfish Head Craft Brewery and South Rookery Golf Course. Looking to enjoy an event or a game while in town? See what's happening at Sports at the Beach or Georgetown Speedway. Kayaking, power boating and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Contessa Suite,
No added fees or cleaning charges.
Contessa's Suite
The Charleston of Milton Inn is located in the heart of Milton's Historic District. Within walking distance to all downtown shops, restaurants, Doghead Fish Brewery, Milton Theater, Waterfront Parks, etc. 7 Miles to Broadkill Beach. 12 miles to Cape Henlopen State Beach. 14 miles to Rehoboth Outlets and Beach. Our guest suites are located on the second floor. Each feature a King size bed, private En suite bath, private porch, and kitchenette.
The Contessa's Suite Our very spacious accommodations provide individual climate controls, ceiling fans, kitchenette breakfast / workspace. We have super high-speed Wi-Fi 400 Mbps as well as wired internet connection via an Ethernet cable at the breakfast / work area. The smart TVs are equipped with 4K Dolby Vision, UHD, free Netflix, and Prime Video included. TVs are also hard wired to the internet (No Buffering)
The King Bed. Your restful sleep begins with the Westin Heavenly Bed Experience. Enjoy 10 layers of pure comfort on your custom pillow top mattress. Layered with 100 % Egyptian cotton pressed sheets, plush pillows, and imported blankets from Portugal, of seasonal weight. Finished with a King Charles Matelassé Coverlet. Linens and towels are cleaned with Arm & Hammer Free and Clear / Sensitive Skin no dyes or perfume.
Special Requests Encouraged.
. Guests have access to the main porch, foyer, the gardens, and their own guest suite with their private porches. You will have your own kitchenette fully. equipped with micro, refrigerator, toaster, coffee maker etc.
House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children
Children allowed: ages 13–17
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Events
No events allowed
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Pets
No pets allowed
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Smoking
Smoking is not permitted
Photo ID required.
Check in time window 3pm to 9pm unless other arrangements have been previously agreed on.
Please No High Heels. We have wood floors.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock
Frequently asked questions
Is Contessa Suite,
No added fees or cleaning charges. pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Contessa Suite,
No added fees or cleaning charges.?
As of 11 Apr 2026, prices found for a 1-night stay for 2 adults at Contessa Suite,
No added fees or cleaning charges. on 24 July 2026 start from AU$307, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Contessa Suite,
No added fees or cleaning charges.?
On-site parking is available at the property.
What time is check-in at Contessa Suite,
No added fees or cleaning charges.?
Check-in begins at 3:00 PM.
What time is check-out at Contessa Suite,
No added fees or cleaning charges.?
Checkout is at 10:00 AM.
Where is Contessa Suite,
No added fees or cleaning charges. located?
Located in the heart of Milton, this guesthouse is within a 5-minute walk of Milton Historical Society, Lydia Black Cannon Museum and Milton Memorial Park. Milton Theater and Dogfish Head Craft Brewery are also within 1 mile (2 km).
Contessa Suite,
No added fees or cleaning charges. Reviews
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Quick walk to the downtown Milton area, the host Richard was incredibly responsive and accommodating!
I’d absolutely stay here again, what a beautiful place!
What a wonderful stay in this hidden gem! Beautiful room in a Southern Charleston home with stunning porches and landscaping. Our host Richard was excellent and was available when needed…we can’t wait to return!!
This place is beautiful the ground were lovely the owner was very welcoming. It was walkable to a quaint down town with many restaurants and Dogfish Brewery . This was are second time staying there
We just had another perfect stay at The Charleston of Milton Inn. The house, room and grounds are meticulously designed and maintained! and our host, Richard is the best! Already looking forward to our next visit!Lauren & Mike
Lauren A.
Stayed 2 nights in Jul 2025
Verified
10/10 Excellent
John
16 June 2024
beautifully decorated had everything we needed for our weekend stay. Owner was wonderful and helpful. Beautiful place to stay and convenient
My daughter and I stayed here for her lacrosse tournament and we couldn’t have had a better experience. We will definitely come back next year and I highly recommend it!
Beautiful house the room was very decorated beautiful and extremely clean. Richard our host is a wonderful person so nice. We actually passed out cards to friends to stay we loved it so much. Brenda and kevin
Richard our host is a wonderful person. He greeted us and gave us the information we needed to make our stay a pleasant one. The house is beyond description. The detail and beauty of the Inn is over the top. If we come back to De , we will look into staying here again.
Richard is the most wonderful host—he made us feel very welcome and comfortable! The property is just beautiful, with perfectly manicured lawns and gorgeous roses and flowers in the garden. Spacious room, comfortable bed, luxurious sheets and bedding, great shower, and a beautiful balcony porch to unwind at the end of the day. We’ll be back next time we’re in Delaware.
Richard, the owner, was more than hospitable. The property was beautiful, relaxing with great attention to detail. The location in Milton was quiet but close enough for easy beach access. Nearby restaurants and ice cream in Milton were top notch.
Wonderful Experience. The property was meticulously maintained inside and out. Attention to detail was impressive. You couldn’t find something wrong if you looked for it with a magnifying glass! Relaxed atmosphere. This will be our go to property in the area. Richard was an exceptional host.
The Contessa Suite was a wonderful place for our long weekend of exploring the nearby Delaware shore. Located in the charming town of Milton, our room was large, spotlessly clean, meticulously decorated and had all the amenities that we expect in a small inn. We especially liked the large balcony that overlooked the lovely and peaceful lawn/garden below. Richard, our host, was friendly, welcoming and very helpful in recommending businesses in Milton and in suggesting places to explore on the shore.
This property was a relaxing getaway. It was not far from Rehoboth and we were able to enjoy the beach vibes and then return quietness. Owner gave us recommendations for breakfast. Which did not disappoint!
The host was excellent in getting us oriented to the property and the suite, as well as local dining recommendations. He was both attentive to our needs but non-intrusive as well. The suite was very clean and well-appointed.
Wonderful weekend getaway. Richard was a terrific host. Fully appointed and intentional accommodations.
Quaint town with good restaurants and theatre in walking distance. Easy drive to beach
Wonderful host! Lovely setting. Perfect suite - luxurious shower with fluffy towels. Ironed bed linen!!!
Close to downtown restaurants and local beaches. Our third visit.
The Charleston is an absolutely beautiful place to stay. There is great attention to detail. Richard is a wonderful host. Looking forward to staying in the future. :)
This place really stands out in the town. It really looks like a slice of Charleston set in Milton. The grounds, the house, and furnishings were all very nice. I especially like sitting out on the covered porch and relaxing. The host was very hospitable.
This was a perfect quick get away. It was quiet, but close to all the beach activities. The pillows and mattress were so comfortable. I have not slept that well in years. Sitting on the covered balcony was very relaxing. We will be back.
Perfect spot for a getaway at the beach with my daughter. Richard is a wonderful host. The room was very clean, beautifully decorated, lovely garden. Everything was presented with fine detail and care. Highly recommend!
The property was beautiful, our host Richard was very kind and accommodating. I’m not one to usually leave reviews but felt very compelled to do so this time. Will certainly be back again!
My fiance and I really enjoyed our two night stay! The owners were extremely sweet and helpful!
The owners were so sweet and the breakfasts were delicious! Our bedroom was beautiful and we had a great time! Gorgeous place! The only things we would recommend for any future changes would be to make sure the heat is on....really cold our second night, and a bathroom with a shower/shower curtain. Otherwise it was the perfect getaway and we may definitely visit again one day!
Mike T.
Stayed 2 nights in Oct 2022
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