At this oceanfront home, just two houses away from the ocean, you can unwind in style with breathtaking views of the sea. Enjoy a heated swimming pool and surrounding fenced porch with high-end outdoor furniture and a propane gas grill. Indoors, discover 10 bedrooms and 9 bathrooms along with residential elevator access to all three floors.
Reviews
9.89.8 out of 10
Exceptional
Entire home
10 bedrooms10 bathroomsSleeps 22
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
Property amenities
Pool/Spa
Pool
Internet
Available in the house: WiFi
Parking and transport
Onsite parking includes off-street options
Kitchen
Blender
Coffee/tea maker
Dishwasher
Freezer
Hob
Ice maker
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Waffle maker
Bedrooms
10 bedrooms
Bedsheets provided
Sofa bed
Bathroom
9.5 bathrooms
Hair dryer
Towels provided
Living spaces
Fireplace
Living room
Entertainment
Flat-screen TV
Outdoor areas
Balcony
Gas grill
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Ceiling fan
Heating
Pets
Pet friendly
Welcoming dogs only
Up to 23 kg per pet
Suitability/Accessibility
Cobblestone flooring in public areas
Hardwood flooring in public areas
Lift
Tile flooring in public areas
Smoke-free property
Services and conveniences
Iron/ironing board
Things to do
Billiards/pool table
Table tennis
Safety features
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)
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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
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 23 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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
About the area
Rehoboth by the Sea, a neighbourhood in Dewey Beach, is home to this holiday home. While the natural beauty of Cape Henlopen State Park and Rehoboth Beach can be enjoyed by anyone, those looking for an activity can explore Cape May - Lewes Ferry.
East of Maui and Fifer Orchards Local-Fresh Market - Dewey Beach are also worth visiting. Visit our Dewey Beach travel guide
Does 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool have a pool?
Yes, this property has a pool.
Is 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool pet-friendly?
Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 23 kg per pet. Some restrictions may apply, so please contact the property for more details.
How much is parking at 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool?
On-site parking is available at the property.
What time is check-in at 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool?
Check-in begins at 3:00 PM.
Where is 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool located?
Located in Rehoboth by the Sea, this holiday home is within 1 mi (2 km) of Dewey Beach and Rehoboth Beach. Rehoboth Beach Boardwalk is 1.5 mi (2.4 km) away.
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10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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!
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.
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!
Perfect home for a large group, love that every bedroom has its own bathroom. Location to the beach is perfect.
House manager was fantastic! We had a few issues that were quickly resolved, Samantha quickly responded to all our questions. Will return!
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
The house was large enough to accommodate our big group. Eight of the bedrooms had an en suite bathroom which was perfect for our adults only group. The beds and furniture were comfortable. The elevator and heated pool were a real bonus! The kitchen was well equipped with two of each of the appliances. Proximity to the beach was great!
We did have some issues during our stay but the property manager Samantha was always available, responded quickly and did her best to address the problems.
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.
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.
Mary A.
Stayed 7 nights in Jul 2025
Verified
10/10 Excellent
Ben G.
25 Feb 2019
Beautiful house, great host! Perfect for large families who like to cook!
We couldn't have had a better time! House if great for families with young children and other large groups--perfectly well stocked and steps from the beach. We can't wait to stay here again!
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!
We enjoyed every second of our vacation. This was by far the best location we’ve had for our annual family/friends trip. With 4 families with 2+ kids each, this house had plenty to do, plenty of space, and was the perfect combo of comfort and fun. It’ll be hard to top the pool and ping pong table!