10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool

Dewey Beach, Delaware
$1258 avg/night Minimum Stay 1 Nights
Bed 10

Bed

Bath 9

Bath

Home Private Vacation Home

Property Type

Sleep 22

Max Sleeps

Night 1 nights

Min Stay

Luxury, comfort, and breathtaking views describe this home the best! This incredible three story 4,500 sq. ft. house was completed in August 2018 and is just two houses away from the ocean. It has great views of the ocean from inside and outside, is just a few blocks away from downtown Dewey Beach, and less than a mile from downtown Rehoboth Beach the boardwalk.

The house has a massive 2rd floor living area that includes a main seating area; a seating area adjacent to the oval window with perfect ocean view; a dining room seating 12 with adjacent kitchen island seating five more; a sunroom off the main living area with pool/ping pong combination table and a hallway bath with walk-in shower.

The house features a heated swimming pool and a surrounding fenced porch. The propane gas grill and high-end outdoor furniture makes it the preferred place for you, your family, and friends to relax and enjoy the pool and the company. For those who enjoy the outdoors, there is no better place to people watch and take in the ocean breeze than on one of the two open porches.

The home includes off-street parking for 5 cars, plus 2 on-street city parking permits.

The house includes a residential elevator that goes to all 3 floors.

The house has 10 high quality bedrooms and 9 1/2 bathrooms.
Indoors:

The First floor includes the following:
Bedroom with 1 Queen bed w/ attached bathroom/walk-in shower.
Bedroom with 1 King bed w/ attached bathroom/walk-in shower.
Bedroom with 2 Bunk Beds w/ attached bathroom/walk-in shower.
Bedroom with 1 Queen bed w/ attached bathroom/shower w/ tub.
Bedroom with 1 King bed w/ attached bathroom/walk-in shower.
Hallway powder room.

The second floor consists of a massive living area featuring:
Main seating area with a gas heated fireplace and a large flat-screen TV (the Main Seating Area).
Seating area adjacent to the Oval Window (the Oval Seating Area) with great ocean view.
Dining room seating 12, and an adjacent island seating five.
Over stacked gourmet kitchen, with 1 oversized Miele refrigerator and 1 oversized Miele freezer, 3 cooktops, 2 ovens, 2 microwaves, 2 dishwashers, and 1 ice maker.
Sun Room off the main living area with pool/ping-pong combination table.
Hallway bathroom with a walk-in shower.
Another seating area with a flat screen TV, two reclining chairs, a coffee table and a sofa bed. This room commands a great ocean view which makes it a great extra TV/game/hangout room for the kids, in addition to functioning as an extra bedroom.

The Third floor includes the following:
Bedroom with 1 King bed w/ attached bathroom/walk-in shower.
Bedroom with 1 King bed w/ attached bathroom/walk-in shower.
Bedroom with 1 King bed w/ attached bathroom/shower w/ tub.
Living room with a wall-mounted flatscreen TV, two reclining chairs, a coffee table and a sofa bed. This room commands a great ocean view which makes it a great extra TV/game/hangout room for the kids, in addition to functioning as an extra bedroom.
2 Miele washers and dryers.

The house has outdoor gathering/seating areas that include:
2 open porches on the 2nd and 3rd floors. Their high-end outdoor furniture and breathtaking ocean views make them preferred places to relax and enjoy the view.
A heated swimming pool (from May 1st to October 1st) and fenced porch with a propane-fired grill and high-end outdoor furniture.
There is also an outside private hot/cold shower with a dressing area, as well as an ice maker on the first floor.

More great things about the house:
The house features porcelain wood-like tile floors, hardwood floors, granite countertops and custom tile designs in the kitchen and all bathrooms.
All bathrooms have a designer custom-tile shower with niches and glass wall/door or tub/shower combinations.
Every bedroom, including the two rooms with sofa beds, has a ceiling fan and a flatscreen TV.
The 2nd floor main living area has a gas fireplace and a large flatscreen TV.
The house has a fully stocked luxury kitchen that includes high-end appliances including 1 gigantic size Miele refrigerator and freezer, 2 dishwashers, 1 under-counter ice maker, 2 stoves, 2 microwaves, 1 cooktop and plenty of cabinets. Small appliances include 2 coffee makers, 2 four-slice toasters, a restaurant-style Belgian waffle maker, and a blender and more.
High speed wireless Internet throughout the home.
2 Miele washers and dryers conveniently located on 3nd floor.
Central air-conditioning throughout the home, with each floor having its own temperature control unit.
Two tank-less hot water heaters so you won't run out of hot water.
Plenty of silverware, plates, and mugs to go around.
Ironing board and iron, and hair dryer.
16 Beach chairs and 5 Beach umbrellas.

House Rules
Check-in: ‎3‎:‎00‎ ‎PM.
Check-out: ‎10‎:‎00‎ ‎AM.
No smoking.
Children allowed.
Children under 5 do not count in occupancy.
Minimum age of primary renter: 25
Max guests: 22 (sleeps up to 22 adults).
This is a non-smoking residence. $350 Cleaning Fee, $400 Linen Fee, and $1,500 Security Deposit is required on all reservations. The linen fee includes bedding, sheets, and bathroom towels. Bed linens provided for 8 bed rooms and 2 sofa beds. Towels provided for 22 guests.

Cancellation Policy
100% refund if canceled at least 60 days before arrival date.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    10 Bedrooms Bed Sheets Provided Sofa Bed
  • KITCHEN

    Blender Coffee/tea Maker Dishwasher Freezer Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Includes Off-street Options
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Gas Grill Outdoor Furniture
  • POOL/SPA

    Pool
  • BATHROOMS

    9.5 Bathrooms Hair Dryer Towels Provided
  • ENTERTAINMENT

    Pool Or Billiards Table Table Tennis Flat-screen TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Ceiling Fan Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Cobblestone Flooring In Public Areas Elevator Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Tile Flooring In Public Areas

CheckIn Check-in : 03:00 PM CheckOut Check-out : 07:00 PM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 22

Map Map

School District Rates & Availability

Review Review

  • Karin R.

    Submitted Sep 21, 2025

    Stayed Sep 13, 2025

    Great location right off the beach! Lots of room for our group of 20. Kitchen is fairly well-stocked and has two of every appliance -- fridge, dishwasher, stove, coffee maker, etc. We were there late in the season, so under the couch and under some of the beds could have been cleaner, but nothing we couldn't live with. One of the upstairs bedrooms has an AC return in the closet, so it was noisy at times -- and has no rod to hang clothes -- but, again, nothing we couldn't live with. We enjoyed our stay and plan to return!

  • Janice S.

    Submitted Sep 13, 2025

    Stayed Sep 6, 2025

    Everything was wonderful. As in the past the pool wasn’t warm til Thursday. There is a block on the front step on the right that is not attached. It sends you off balance. Also if a railing could be put on the front and back steps would be good. Double check the vacuum as we could not get the beater bar to rotate. We love your property. It is perfect for a large group. Especially nice to all be able to sit and enjoy a meal together. We will probably be back next year

  • Lorri G.

    Submitted Aug 11, 2025

    Stayed Aug 2, 2025

    All as represented. Check in was easy. All requests accommodated immediately.

  • Beth H.

    Submitted Aug 2, 2025

    Stayed Jul 26, 2025

    Great home and perfect location. Steps from the beach and walkable to both Dewey and Rehoboth.

  • Mary A.

    Submitted Jul 23, 2025

    Stayed Jul 5, 2025

    The place was fixed up nice. Samantha is wonderful to work with. There was a small water problem but it was taken care of. The place is great.

  • Keith S.

    Submitted Jul 23, 2025

    Stayed Jun 14, 2025

    The location of the property to the beach and it being

  • Samantha G.

    Submitted Jul 20, 2025

    Stayed Jul 12, 2025

    Very nice property and well maintained.

  • Valerie H.

    Submitted Jul 5, 2025

    Stayed Jun 28, 2025

    This is our third stay at this property. We love that every bedroom has a bathroom and that the house is a very short walk to the beach. It is perfect for multiple families with children of varying ages.That being said, after three years of being in this property, I would hope to see some updates- new duvet covers, new rugs, landscaping, etc. For the cost, it would be nice to see the owner put some money back into it in the form of charm and modest updates.We ran into one issue and were short a bathroom and bedroom for our stay due to a leak and lingering moisture in the bathroom that needed to be remediated. The property manager, Sam, was a breeze to deal with- always informative and responsive. We would definitely stay again, but would like to see the owner update some things.

  • Anita T.

    Submitted Sep 25, 2024

    Stayed Sep 7, 2024

    The house and location is amazing. The property manager Samantha answered all questions ahead of time and 14 High School Reunion Ladies had a wonderful time. No issues at all with the house. Hope to book it again in the future.

  • Elizabeth M.

    Submitted Sep 24, 2024

    Stayed Aug 24, 2024

    The location and amenities are amazing! Samanatha was

  • margo H.

    Submitted Aug 24, 2024

    Stayed Aug 17, 2024

    Our extended family just finished our second beach vacation at 10 Chicago Street. We had a wonderful time with seven cousins under the age of seven running around the house and enjoying the pool. we had three generations staying there. The kitchen is fabulous as We have multiple needs for food prep space. We are planning a return next yearwewe had multiple staying

  • Byulah C.

    Submitted Aug 9, 2024

    Stayed Aug 4, 2024

    The house was perfect for our extended family of 17. The elevator was great for elderly grandparents, and the pool along with close proximity of beach was fantastic for our high school and college age family members. The appliances were perfect for a big house: 2 of each stove tops, fridges, ovens, dishwashers, and in addition a standalone freezer and ice maker. Highly recommend this place!

  • Linda I.

    Submitted Jul 21, 2024

    Stayed Jul 13, 2024

    The summary online was accurate - the house lived up to our expectations. The rooms were well furnished, the kitchen had all the dishes, glasses, appliances you needed and along with the pool, toys, and beach chairs a great time. An added benefit was having the beach literally 100 feet away. That portion of the beach was quiet, well maintained, lifeguards were all attentive and we had a great time.

  • Samantha G.

    Submitted Jul 14, 2024

    Stayed Jul 6, 2024

    We are repeat renters. This home is well taken care of and has all the amenities that we prefer.

  • susan b.

    Submitted Jun 28, 2024

    Stayed Jun 1, 2024

    awesome

  • Valerie H.

    Submitted Jun 27, 2024

    Stayed Jun 15, 2024

    This is our second stay and it did not disappoint. In fact, it was even better than last year with new fans on the porch off of the main floor, fresh paint, and AC that was pumping! The property manager is so accommodating and responsive. We have already booked for next year and can't wait to come back!

  • Jonathan T.

    Submitted Jun 24, 2024

    Stayed Jun 8, 2024

    Fit 18 of our family perfectly. Close to the beach and the pool was awesome

  • Janice S.

    Submitted Jun 17, 2024

    Stayed May 17, 2024

    The property is great. But being the first one of the season we have had to work through a few bugs each stay. The pools heater was an issue again this year so we did not have heat for 3 days to warm up the water. The air conditioning was not working properly either. A repair man was sent to fix both issues quickly. Everyone we talked to was very nice and helpful. Samantha is wonderful and an asset for this property.

  • Donna F.

    Submitted Jun 2, 2024

    Stayed May 25, 2024

    We had 18 people ranging from 1 year old to 67 years old. The property was perfect for all of us. The 2nd floor has the best set up for groups of our size that we've ever seen in a rental property -- huge well-stocked kitchen, large dining table, very big wraparound sofa. And the decks were great too. One detail to recognize is that there are 7 bedrooms with baths attached. The other two sleeping areas are dens, each with a double pullout couch (one on 2nd floor the other on third floor). Second floor den is next door to the only bathroom that isn't in a bedroom. Third floor den has to use that same second floor bathroom. It wasn't a problem for our group at all. The pullout sofas are comfortable. Samantha, the property manager, was easily accessible.

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Total

Includes taxes and fees
$1,258+
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