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Contessa Suite, Bed and Breakfast, No added fees or cleaning charges.

Travelers enjoy garden views from private porches or take a short stroll to historic downtown shops from this peaceful retreat in Milton's Historic District.

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The Charleston of Milton Inn's Contessa's Suite provides a tranquil getaway in historic Milton. Guests relax on private porches, sleep on Westin Heavenly Beds, and connect with super high-speed Wi-Fi. Beautiful gardens and main porch areas are accessible to all visitors.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Free WiFi
  • Laundry
  • Kitchen

About the neighborhood

Located in Milton, this guesthouse is in the city center 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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Milton, DE

What's nearby

  • Lydia Black Cannon Museum - 3 min walk - 0.3 km
  • Milton Historical Society - 3 min walk - 0.3 km
  • Milton Memorial Park - 5 min walk - 0.4 km
  • Milton Theater - 6 min walk - 0.6 km
  • Dogfish Head Craft Brewery - 17 min walk - 1.4 km

Getting around

  • Georgetown, DE (GED-Sussex County) - 13 min drive

Restaurants

  • ‪McDonald’s - ‬14 min walk
  • ‪Zava Cafe Milton - ‬6 min walk
  • ‪China Wok - ‬14 min walk
  • ‪Dogfish Head Craft Brewery - ‬19 min walk
  • ‪Po' Boys Creole Restaurant - ‬17 min walk

About this property

Contessa Suite, Bed and Breakfast, No added fees or cleaning charges.

Guesthouse by the sea
Contessa Suite, Bed and Breakfast, No added fees or cleaning charges. provides amenities like a garden and laundry facilities. Guests can connect to free in-room WiFi.
You'll also enjoy perks such as:
  • Smoke-free premises and beach towels
  • Guest reviews speak highly of the first-rate property condition
Room features
All guestrooms at Contessa Suite, Bed and Breakfast, No added fees or cleaning charges. boast thoughtful touches such as air conditioning, in addition to amenities like free WiFi and dining tables.
Extra amenities include:
  • Bathrooms with showers and hair dryers
  • Porches or lanais, outdoor lighting, and kitchens

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King Charles Suite, Bed & Breakfast, No added fees or cleaning charges.
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Property amenities

Internet

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

Conveniences

  • Laundry facilities

Outdoors

  • Beach loungers
  • Beach towels
  • Garden

More

  • Smoking not allowed

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
Information provided by the property may be translated using automated translation tools

Rules

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.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
Onsite 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

Frequently asked questions

Is Contessa Suite, Bed and Breakfast, No added fees or cleaning charges. pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Contessa Suite, Bed and Breakfast, No added fees or cleaning charges.?

Check-in begins at 3:00 PM.

What time is check-out at Contessa Suite, Bed and Breakfast, No added fees or cleaning charges.?

Check-out is at 10:00 AM.

Where is Contessa Suite, Bed and Breakfast, 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 mi (2 km).

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Reviews

Contessa Suite, Bed and Breakfast, No added fees or cleaning charges. Reviews

10

Exceptional

10

Cleanliness

10

Location

10

Staff & service

10

Property conditions & facilities
Rating 10 - Excellent. 67 out of 67 reviews
Rating 8 - Good. 0 out of 67 reviews
Rating 6 - Okay. 0 out of 67 reviews
Rating 4 - Poor. 0 out of 67 reviews
Rating 2 - Terrible. 0 out of 67 reviews

Reviews

10/10 Excellent

Lauren A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 2 nights in Jul 2025

10/10 Excellent

Joe R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pleasant and relaxing place to stay!

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.
Stayed 2 nights in May 2025

10/10 Excellent

Michael

Liked: Cleanliness, amenities, property conditions & facilities
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.
Stayed 2 nights in Jun 2025

10/10 Excellent

Pamela S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Randall

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

graham

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

Pat and Gary R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

David P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Laura W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Katrina H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Pat R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

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

10/10 Excellent

Dawn T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

WOW

This place is amazing. The house is beautifully decorated and maintained. The owners have thought of everything to make your stay enjoyable. Fridge is stocked with some water, ketchup, mustard and mayo. Creamer, coffee, tea sugars. And even a box of kleenex in the room. The privite porch is beautifully decorated and nice to sit out and watch the beautiful birds and admire the garden. So many thoughtful extras. Just a short walk to Milton Theater and Irish Eyes restaurant.
Stayed 2 nights in May 2025

10/10 Excellent

Jill C., Ventnor, NJ

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Holly R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

dave b.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Ed & Vicky S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Kathy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Jennifer W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Kari B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Joan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Brett P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Lauren A., Freeland

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Karen R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

somie r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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

Austin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 2 nights in Jul 2025