See all properties
Entire home

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

Choose dates to view prices

your current months are November, 2024 and December, 2024.
November 2024
December 2024

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

Beach
Terrace/patio
Fridge, microwave, oven, stovetop
Flat-screen TV, fireplace, table tennis
Beach

Reviews

9.8 out of 10

Exceptional

Entire home

10 bedrooms10 bathroomsSleeps 22

Popular amenities

  • Washer
    Washer
  • Pool
    Pool
  • Outdoor space
    Outdoor space
  • Pet-friendly
    Pet-friendly
  • Parking available
    Parking available
  • Kitchen
    Kitchen

Explore the area

Map
Dewey Beach, DE
  • Dewey Beach
    1 min walk
  • East of Maui
    4 min walk
  • Silver Lake
    6 min walk
  • Cape May, NJ (WWD-Cape May County)
    127 min drive

Room options

About the area

Dewey Beach

Rehoboth by the Sea stay.At this Rehoboth by the Sea vacation home, you'll be within a 5-minute walk of Dewey Beach and East of Maui. Fifer Orchards Local-Fresh Market - Dewey Beach and Silver Lake are also within half a mile (1 km).
View more Vacation homes in Dewey BeachOpens in a new window

What's nearby

  • Dewey Beach - 1 min walk
  • Rehoboth Beach - 3 min drive
  • Rehoboth Beach Convention Center - 4 min drive
  • Rehoboth Beach Boardwalk - 4 min drive
  • Tanger Outlets - 4 min drive

Getting around

  • Georgetown, DE (GED-Sussex County) - 31 min drive

Restaurants

  • ‪Rusty Rudder - ‬17 min walk
  • ‪Dewey Beer Company - ‬7 min walk
  • ‪Woody's Dewey Beach - ‬9 min walk
  • ‪Nalu Surf Bar - ‬16 min walk
  • ‪Wings To Go - ‬9 min walk

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

  • WiFi available

Parking and transportation

  • Onsite parking includes off-street options
  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Ice maker
  • Freezer
  • Coffee/tea maker
  • Blender

Bedrooms

  • 10 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 9.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Flat-screen TV
  • Pool or billiards table
  • Table tennis
  • Arcade/game room

Outdoor areas

  • Balcony
  • Gas grill
  • Outdoor furniture

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Cobblestone flooring in public areas
  • Elevator
  • Hardwood flooring in public areas
  • Tile flooring in public areas
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

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)

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Special check-in instructions

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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

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
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 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

Property is also known as

Vrbo Property
10 Chicago Street 10 Bedrooms 91/2 Path Ocean Block w/ Pool

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 48 out of 54 reviews" "
Rating 8 - Good. 5 out of 54 reviews" "
Rating 6 - Okay. 1 out of 54 reviews" "
Rating 4 - Poor. 0 out of 54 reviews" "
Rating 2 - Terrible. 0 out of 54 reviews" "

9.0/10

Cleanliness

Reviews

10/10 Excellent

Anita T.

Liked: Cleanliness
Great Ladies Getaway
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.
Stayed 7 nights in Sep 2024

10/10 Excellent

Elizabeth M.

Liked: Cleanliness
Perfect for big group and multi-generational family vacation
The location and amenities are amazing! Samanatha was
Stayed 7 nights in Aug 2024

10/10 Excellent

margo H.

Liked: Cleanliness
Family reunion in Dewey Beach
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
Stayed 7 nights in Aug 2024

10/10 Excellent

Byulah C., Philadephia, PA

Liked: Cleanliness
Great house and great location
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!
Stayed 5 nights in Aug 2024

10/10 Excellent

Linda I.

Liked: Cleanliness
Great Location
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.
Stayed 7 nights in Jul 2024

10/10 Excellent

Samantha G.

Liked: Cleanliness
PERFECT
We are repeat renters. This home is well taken care of and has all the amenities that we prefer.
Stayed 7 nights in Jul 2024

10/10 Excellent

susan b.

Liked: Cleanliness
family vacation
awesome
Stayed 7 nights in Jun 2024

10/10 Excellent

Valerie H.

Liked: Cleanliness
Repeat Customers
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!
Stayed 7 nights in Jun 2024

10/10 Excellent

Jonathan T.

Liked: Cleanliness
Great house in Dewey
Fit 18 of our family perfectly. Close to the beach and the pool was awesome
Stayed 7 nights in Jun 2024

10/10 Excellent

Janice S.

Liked: Cleanliness
Returning renters
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.
Stayed 7 nights in May 2024

10/10 Excellent

Donna F.

Liked: Cleanliness
Perfect for large families
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.
Stayed 7 nights in May 2024

6/10 Okay

Meg M., Where do you live?

Beautiful House in need of care
This is the second time we have stayed at this home. The first time it was great. Sadly, our second visit was plagued by problems resulting from the lack of upkeep of this property. A short list includes: Broken pool gate, Outdoor deck lighting smashed with exposed wiring, broken pool furniture and old linens and stained towels, front door that wouldn't lock, a leak in sitting room ceiling. I could go on but I'm sure you get the point. We would love to return someday But would need proof of maintenance. We were given the excuse that it was the end of the season. Seems odd, but we paid the full seasonal rate.
Stayed 7 nights in Sep 2023

10/10 Excellent

Bruce H.

Liked: Cleanliness
The entire house including bedrooms were large and very comfortable. Location was perfect.
I couldn’t have been more pleased with everything.
Stayed 7 nights in Sep 2023

8/10 Good

Kathy S.

Perfect for us!
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.
Stayed 7 nights in Sep 2023

8/10 Good

Mary A.

Stressful
We love the property as well as the property manger. It was VRBO I was not happy with. I did not receive the door code and I didn't feel VRBO help us. VRBO said they would put us in a motel but we had 22 people with cars full of food and a grocery order coming that evening and VRBO didn't seem to care. I felt VRBO could of done more to help the situation. The owner and property manager helped which made our stay wonderful.
Stayed 7 nights in Aug 2023

10/10 Excellent

Samantha G.

Liked: Cleanliness
wonderful week with the family
well kept house , close to the beach. We've been visiting Delaware for about 20 years. hope to be back next year.
Stayed 7 nights in Jul 2023

10/10 Excellent

Claudia N.

Liked: Cleanliness
Great Home for Family Reunion!
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!
Stayed 7 nights in Jul 2023

10/10 Excellent

Valerie H.

Liked: Cleanliness
Great Property
This is a great property for a large group. There is plenty of space to gather and plenty of space if you need some quiet time. The fact that each bedroom has its own bathroom is a great feature. We loved having the pool as an option for the kids and when the weather was chilly, they adjusted the heat so that the kids could swim without complaint. Highly recommend and would certainly rent again.
Stayed 7 nights in Jun 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness
Great House
This house was great for our large family and friends. It was large enough that we all had our own space and the location was perfect. We would go back again! Thank you!
Stayed 7 nights in Jun 2023

8/10 Good

Gianina K.

Liked: Cleanliness
The most comfortable beds!!
beautiful house in the perfect location!
Stayed 7 nights in Sep 2022

10/10 Excellent

Meg M., Where do you live?

Liked: Cleanliness
Fall friends getaway
This was a great property for our group of fun over 65ers. This kitchen has the best design and appliances any cook could want. It was perfect as we like to cook together. Proximity to the beach was key as was the fabulous pool. Would highly recommend.
Stayed 7 nights in Sep 2022

10/10 Excellent

margo H.

Liked: Cleanliness
the perfect family reunion
Rehoboth by the Sea was the perfect place for our large family reunion. We had many needs for the group of 19 which included 7 children under age 5, one member in a wheelchair, and various kosher, gluten free or vegetarian meal requests. The kitchen was able to accommodate all of us. The pool is fantastic and the house is really a few steps from the beach. We all want to go back
Stayed 7 nights in Aug 2022

10/10 Excellent

richard k.

Liked: Cleanliness
Review of 10 chicAgo dewey beach delaware
Beautiful property in a great location
Stayed 7 nights in Jul 2022

10/10 Excellent

Deanna E., Cinnaminson, USA

Liked: Cleanliness
Wonderful family reunion
Had a wonderful stay. The home fit 20 of us nicely. Great location close to beach. Samantha, the property manager, was great. She was very attentive to any issues that came up during our stay. Thank you for a great family reunion.
Stayed 7 nights in Jul 2022

10/10 Excellent

Liz G.

Liked: Cleanliness
Location can't be beat!
Amazing house for our family vacation. Plenty of room for all 18! Location couldn't be better-short walk to town and beach. Comfortable furniture and beds. Outdoor Pool was the highlight! Our contact, Samantha was very responsive to all our needs! Highly recommend 10 Chicago St.
Stayed 7 nights in Jul 2022