Entire home
10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool
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Reviews
9.8 out of 10
Exceptional
10 bedrooms9+ bathroomsSleeps 22
Popular amenities
Explore the area

Dewey Beach, DE
- Place, Dewey Beach1 min walk
- Place, Fifer Orchards Local-Fresh Market - Dewey Beach5 min walk
- Place, Rehoboth Beach2 min drive
- Airport, Ocean City, MD (OCE-Ocean City Municipal)49 min drive
Rooms & beds
10 bedrooms (sleeps 22)
9 bathrooms, 1 half bathroom
Bathroom 1
Bathroom 2
Bathroom 3
Bathroom 4
Bathroom 5
Bathroom 6
Bathroom 7
Bathroom 8
Bathroom 9
Bathroom 10
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
About this property
10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool
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.
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.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
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10.0 out of 10, Exceptional, (2 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed: dogs less than 23 kg per pet (limit 2 pets total)
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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Dewey Beach
Rehoboth by the Sea, a neighbourhood in Dewey Beach, is home to this holiday home. The area's natural beauty can be seen at Rehoboth Beach and Lewes Beach. East of Maui and Fifer Orchards Local-Fresh Market - Dewey Beach are also worth visiting.

Dewey Beach, DE
What's nearby
- Dewey Beach - 1 min walk - 0.1 km
- Fifer Orchards Local-Fresh Market - Dewey Beach - 5 min walk - 0.4 km
- Silver Lake - 6 min walk - 0.6 km
- Rehoboth Beach - 2 min drive - 1.4 km
- Rehoboth Beach Boardwalk - 4 min drive - 2.8 km
Getting around
Restaurants
- The Starboard - 8 min walk
- Woody's Dewey Beach - 8 min walk
- Dewey Beer Co. - 7 min walk
- Grotto Pizza - 13 min walk
- Starboard Claw - 9 min walk
Frequently asked questions
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.0/10
Cleanliness
9.8/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
2 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2025
10/10 Excellent
Samantha G.
20 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Samantha G.
Stayed 7 nights in Jul 2025
10/10 Excellent
Keith S.
23 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Beach House
Keith S.
Stayed 7 nights in Jun 2025
10/10 Excellent
Mary A.
23 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary A.
Stayed 7 nights in Jul 2025
10/10 Excellent
Lorri G.
11 August 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lorri G.
Stayed 7 nights in Aug 2025
10/10 Excellent
Elizabeth M.
24 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for big group and multi-generational family vacation
Elizabeth M.
Stayed 7 nights in Aug 2024
10/10 Excellent
Ben G.
25 February 2019
Beautiful house, great host! Perfect for large families who like to cook!
Ben G.
Stayed 4 nights in Feb 2019
10/10 Excellent
richard k.
7 August 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Review of 10 chicAgo dewey beach delaware
richard k.
Stayed 7 nights in Jul 2022
10/10 Excellent
Karin R.
21 September 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Karin R.
Stayed 7 nights in Sep 2025
10/10 Excellent
Bruce H.
4 October 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
The entire house including bedrooms were large and very comfortable. Location was perfect.
Bruce H.
Stayed 7 nights in Sep 2023
10/10 Excellent
Brooks and Laurel N.
26 September 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fabulous
Brooks and Laurel N.
Stayed 7 nights in Sep 2021
10/10 Excellent
Jonathan T.
24 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house in Dewey
Jonathan T.
Stayed 7 nights in Jun 2024
10/10 Excellent
susan b.
28 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
family vacation
susan b.
Stayed 7 nights in Jun 2024
10/10 Excellent
Carol C.
16 August 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect for Large Family Vacation
Carol C.
Stayed 7 nights in Aug 2021
10/10 Excellent
Samantha G.
27 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
wonderful week with the family
Samantha G.
Stayed 7 nights in Jul 2023
10/10 Excellent
Samantha G.
14 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
PERFECT
Samantha G.
Stayed 7 nights in Jul 2024
10/10 Excellent
Sandra D.
5 September 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Can’t beat the location
Sandra D.
Stayed 7 nights in Aug 2021
10/10 Excellent
Verified traveller
21 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House
Verified traveller
Stayed 7 nights in Jun 2023
10/10 Excellent
Carol C.
14 July 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
10 Chicago is a perfect 10!
Carol C.
Stayed 6 nights in Jul 2020
10/10 Excellent
Linda I.
21 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location
Linda I.
Stayed 7 nights in Jul 2024
10/10 Excellent
Anita T.
25 September 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Ladies Getaway
Anita T.
Stayed 7 nights in Sep 2024
10/10 Excellent
Valerie H.
27 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Repeat Customers
Valerie H.
Stayed 7 nights in Jun 2024
10/10 Excellent
Byulah C.
9 August 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house and great location
Byulah C.
Stayed 5 nights in Aug 2024
10/10 Excellent
Guy T.
9 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Beach Vacation
Guy T.
Stayed 7 nights in Jul 2022
10/10 Excellent
Claudia N.
18 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Home for Family Reunion!
Claudia N.
Stayed 7 nights in Jul 2023
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