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Contessa Suite, No added fees or cleaning charges.

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Exterior
Interior
1 bedroom, iron/ironing board, free WiFi, bed sheets
Outdoor dining
Fridge, microwave, coffee/tea maker, toaster

Reviews

10 out of 10
Exceptional

Popular amenities

  • Parking available
  • Air conditioning
  • Kitchen
  • Free WiFi

Explore the area

Map
Milton, DE
  • Milton Theater
    ‪4 min walk‬
  • Dogfish Head Craft Brewery
    ‪16 min walk‬
  • Sports at the Beach
    ‪10 min drive‬
  • Cape May, NJ (WWD-Cape May County)
    ‪107 min drive‬

Room options

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About this property

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.

Our customers tell us that they can't get enough of the overall property condition at this guesthouse. During your stay, you're just a quick walk from Milton Historical Society.
  • Free WiFi
  • Steps from Milton Historical Society and 3 minutes on foot from Lydia Black Cannon Museum
Contessa Suite, No added fees or cleaning charges. offers its guests a garden. The front desk is open around the clock.

This Milton guest house is smoke free.

Property manager

Richard Siess

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Internet access

Outdoors

  • Beach loungers
  • Beach towels
  • Garden

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • TV

Food and drink

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dining table
  • Ice maker
  • Kitchen
  • Microwave
  • Paper towels
  • Refrigerator
  • Toaster

More

  • Air conditioning
  • Dryer
  • Heating
  • Iron/ironing board

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Contessa Suite, No added fees or cleaning charges. Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 53 out of 53 reviews
Rating 8 - Good. 0 out of 53 reviews
Rating 6 - Okay. 0 out of 53 reviews
Rating 4 - Poor. 0 out of 53 reviews
Rating 2 - Terrible. 0 out of 53 reviews

10/10

Cleanliness

10/10

Staff & service

9.0/10

Amenities

10/10

Property conditions & facilities

Reviews

10/10 Excellent

Randall

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 3 nights in Jul 2024

10/10 Excellent

David P.

Liked: Cleanliness
A slice of Charleston
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.
Stayed 2 nights in Sep 2024

10/10 Excellent

dave b.

Liked: Cleanliness
Absolutely amazing!!!!
Pictures only begin to tell the story! Words from all the other reviews help describe the experience. Richard was a fantastic host! The place was immaculate, the grounds and landscaping were absolutely beautiful, the design and character and attention to every detail was covered to make our stay beyond our expectations!
Stayed 4 nights in Aug 2024

10/10 Excellent

Katrina H.

Liked: Cleanliness
A beach treasure
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!
Stayed 2 nights in Jul 2024

10/10 Excellent

Laura W.

Liked: Cleanliness
Perfect get away
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.
Stayed 2 nights in Jul 2024

10/10 Excellent

Holly R.

Liked: Cleanliness
True Southern Charm in Milton
Where to start. The beautiful grounds, the beautiful porch as you walk in playing beautiful music, then you approach your suit with everything that you need and more. Richard and Steve truly captured the essence of Southern charm 5 stars all the way!
Stayed 3 nights in Jul 2024

10/10 Excellent

Ed & Vicky S.

Liked: Cleanliness
The Charleston of Milton
This is one of the nicest places we have ever stayed. Richard welcomed us warmly and gave us a brief explanation of the property’s history. The yard is landscaped nicely with a variety of trees, flowers and ornaments. Our room was beautifully furnished and a perfect size for our 2 night stay and was supplied with all the basic necessities in the kitchenette and bathroom. If we ever need a place to stay in southeast Delaware, this is the first place we will try to reserve.
Stayed 2 nights in Jul 2024

10/10 Excellent

Karen R.

Liked: Cleanliness
A gem
What a gorgeous and peaceful spot. The inn was impeccably designed and decorated, and extremely comfortable. We had our coffee in the mornings on our balcony looking over the garden. We slept deeply. A short walk around the corner brings you to the main area of the little town of Milton, with homemade ice cream and a couple of cute cafes and shops. Lewes and the Rehoboth area are not far, so it's easy to spend a day at the beach or go out to dinner, and then return to this oasis of calm. Richard and Steve were kind and friendly without being intrusive, the perfect balance for innkeepers. We were visiting nearby family, and I look forward to staying at the inn again on our next visit. (If I had one tiny suggestion, it would be room darkening material on the windows, but the curtains are so pretty that I don't know what would work without spoiling the room. But this is nit picking on a wonderful place.)
Stayed 5 nights in Jun 2024

10/10 Excellent

Pamela S.

Liked: Cleanliness
Relaxing escape from hustle & bustle of beach
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!
Stayed 2 nights in Jun 2024

10/10 Excellent

Tara W.

Liked: Cleanliness
Wonderful Stay!
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!
Stayed 2 nights in Jun 2024

10/10 Excellent

Kathy B., Coventry, RI

Liked: Cleanliness
WONDERFUL!!
This is the most spectacular place that I have stayed ever! It's beautiful; so clean, comfortable, (especially the bed & multiple pillows), quiet. It was so relaxing that I didn’t want to leave. The property is just so stunning! The hosts are so incredibly welcoming! I had several engaging conversations with Richard!! I just loved my stay & would stay there again!! ❤️
Stayed 4 nights in Jun 2024

10/10 Excellent

John

Travelled with partner
beautifully decorated had everything we needed for our weekend stay. Owner was wonderful and helpful. Beautiful place to stay and convenient
Stayed 2 nights in Jun 2024

10/10 Excellent

graham

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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
Stayed 2 nights in May 2024

10/10 Excellent

Brett P.

Liked: Cleanliness
Great spot in downtown Milton
I am from the area and had to go back for family business. Richard was an amazing and gracious host. The property was beautiful with a spacious room, comfortable bed, very clean and tasteful decor. If you're going to spend the money, this is 200% better than any hotel in the area you'll find. I highly recommend this place. I have posted numerous reviews on VRBO and this has my highest recommendation. Thanks very much for the great stay! 1 very, very small caveat, these rooms are for adults only. I do not recommend them for children. A lot of glass and breakable items.
Stayed 3 nights in Apr 2024

10/10 Excellent

Pat and Gary R.

Liked: Cleanliness
Wouldn’t stay anywhere else
Wonderful host! Lovely setting. Perfect suite - luxurious shower with fluffy towels. Ironed bed linen!!! Close to downtown restaurants and local beaches. Our third visit.
Stayed 5 nights in Oct 2023

10/10 Excellent

Rebecca R.

Liked: Cleanliness
Beautiful Getaway
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. :)
Stayed 2 nights in Sep 2023

10/10 Excellent

Kari B.

Liked: Cleanliness
Loved it
Amazing property and wonderful host! We spent the weekend for our anniversary. The home is beautiful, as was our room. We especially enjoyed sitting out on the balcony. Restaurants are within walking distance so we walked into town each evening and tried a new place to eat. The ice cream from the ice cream shop nearby is good too. The Doghead Fish Brewery and the outlets are all close by and make for good ways to spend the days. Would definitely come back to this one!
Stayed 2 nights in Sep 2023

10/10 Excellent

Jill C., Ventnor, NJ

Liked: Cleanliness
The Charleston of Milton Inn exceeded our expectations!
What a beautiful place in a quaint town. The decor was peaceful, uncluttered, and immaculate. The Inn is a new home with all the charm and beauty of something much older. We had coffee every morning on our private deck overlooking the lawn/ garden. We cannot wait to go back again! Richard is an impressive artist and was a wonderful host.
Stayed 2 nights in Aug 2023

10/10 Excellent

Joan K.

Liked: Cleanliness
Charleston vibe in Milton!
This is a new and gorgeous Inn that looks like it could be in Charleston. Richard is a wonderful host - super personable and responsive. The suites are big and beautiful with lots of lovely touches. The bathroom is also big with a nice walk-in shower and amenities. The Contessa Suite where we stayed has a wonderful balcony with seating, overlooking the beautiful garden. Milton is about a 20-30 minute drive to Lewes and Rehoboth beach. Very centrally located. It is a small town with a wonderful bakery and several restaurants. We will go back there if we visit the area again and highly recommend it.
Stayed 4 nights in Aug 2023

10/10 Excellent

somie r.

Liked: Cleanliness
Anniversary getaway
No matter the occasion, if you’re in search of a spotless cozy private oasis, The Charleston of Milton Inn is your place! Richard, our host, has quite literally thought of everything to ensure their guests comfort. From the second you pull up, you feel like you’re in a southern bed & breakfast. Soft music welcomes you to the private porch and beautifully landscaped garden. Our room was perfect. Fresh clean plush (better than) hotel towels & robes made us feel like we were being pampered. The what felt like, 900 + thread count sheets were a bonus, but then they went up a notch by ironing them! And the kitchenette. It may be tiny, but it contained everything you need to heat & store your food, or enjoy a hot cup of tea/coffee. There was even coffee creamer. And not the powdery kind, real cream. We thoroughly enjoyed relaxing on our private balcony enjoying the sounds of nature, and watching the bunnies run around the garden. Do yourself a favor and book yourself this special experience.
Stayed 2 nights in Aug 2023

10/10 Excellent

Jennifer W.

Liked: Cleanliness
20 year wedding anniversary
Richard you were so welcoming and it was a pleasure to stay in the Contessa Suite! It was immaculate and comfortable!! The decor was beautiful! We enjoyed the small town feel, like stepping back in time and living at a relaxing, slower pace! Wonderful place to visit if you want a relaxing vacation to recharge!! The garden is beautiful w the cozy balcony perfect for escaping into a book!
Stayed 4 nights in Jul 2023

10/10 Excellent

Pat R.

Liked: Cleanliness
Fabulous
Always Aplus. Elegant enjoyable and engaging Luxurious stunning fun great gardens
Stayed 6 nights in Aug 2023

10/10 Excellent

Mark E.

Liked: Cleanliness
Excellent in all aspect
This is a lovely facility, in a great location. It is near enough to the beach communities, while being away from the throng and traffic. Easy walk into the charming downtown Milton, with good restaurants, coffee shop, etc. Richard is meticulous and has though of everything one might need. A real find!
Stayed 2 nights in Jul 2023

10/10 Excellent

Lauren A., Freeland

Liked: Cleanliness
Perfect!
We loved staying at The Charleston! The room is perfect, and the entire property is well appointed. Whether we were in our room, on our private balcony or enjoying one of the many seating areas on the grounds, the atmosphere is calm and cozy. Everything is clean and perfectly manicure and beautifully decorated. There are also little extras everywhere... coffee, tea, creamer, chocolates. The bathroom has ample space for hanging towels and my cosmetic bag. If there would have been anything we would have needed, our host, was there to help! Thanks, Richard, for another wonderful summer escape. Looking forward to seeing you soon!
Stayed 2 nights in Jul 2023

10/10 Excellent

Catherine M.

Liked: Cleanliness
Perfect
We stayed at the Charleston in Milton for three days to celebrate our anniversary. Everything was perfect from beginning to end. I can’t say enough about the host Richard, he makes sure every need is met and has a wonderful sense of humor. The home and property are beautiful. There are a lot of cute shops and restaurants within walking distance. If you were looking for a relaxing stay away from the crowds this is your place.
Stayed 3 nights in Jul 2023