Entire home

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

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

A two-story house with a swimming pool, outdoor furniture, and a covered patio area.
A kitchen with granite countertops, wooden cabinets, a stainless steel sink, and a range hood.
An aerial view of a coastal residential area with houses, a beach, and a lake.
A cozy living room with a sofa, armchair, and a round table.
A multi-story residential building with a balcony on the second floor, a covered front porch, and a driveway.

Reviews

9.6 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Ping pong on-site
    A rare find — challenge friends and family to endless matches.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Rehoboth Beach Boardwalk

Popular amenities

  • Balcony
  • Swimming pool
  • Dog-friendly
  • Outdoor barbecue
  • High-speed internet
  • Air-conditioning

Explore the area

View map
Dewey Beach, DE
  • Place, Dewey Beach
    ‪1 min walk‬
  • Place, Rehoboth Beach Boardwalk
    ‪12 min walk‬
  • Place, Rehoboth Beach
    ‪12 min walk‬
  • Airport, Ocean City, MD (OCE-Ocean City Municipal)
    ‪58 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

Add dates for prices

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About the area

Dewey Beach

Rehoboth by the Sea, a neighbourhood in Dewey Beach, is home to this holiday home. Shoppers can check out Tanger Outlets, while everyone can enjoy the natural beauty of Rehoboth Beach and Bethany Beach Beaches. Ready for a night out? Consider Rehoboth Beach Public Library and Zogg's Raw Bar & Grill.
View more Holiday homes in Dewey BeachOpens in a new window
Map
Dewey Beach, DE

What's nearby

  • Dewey Beach - 1 min walk - 0.1 km
  • Silver Lake - 6 min walk - 0.6 km
  • Bottle & Cork - 9 min walk - 0.8 km
  • Rehoboth Beach Boardwalk - 12 min walk - 1.1 km
  • Rehoboth Beach - 12 min walk - 1.1 km

Getting around

  • Georgetown, DE (GED-Sussex County) - 34 min drive

Restaurants

  • ‪The Starboard - ‬8 min walk
  • ‪Rusty Rudder - ‬17 min walk
  • ‪Above the Dunes - ‬4 min drive
  • ‪Dewey Beer Co. - ‬7 min walk
  • ‪Woody's Dewey Beach - ‬8 min walk

Frequently asked questions

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.

What time is check-out at 10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool?

Checkout is at 10:00 AM.

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 mile (2 km) of Dewey Beach, Rehoboth Beach and Rehoboth Beach Boardwalk. East of Maui and Fifer Orchards Local-Fresh Market - Dewey Beach are also within 10 minutes.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 59 out of 70 reviews
Rating 8 - Good. 8 out of 70 reviews
Rating 6 - Okay. 3 out of 70 reviews
Rating 4 - Poor. 0 out of 70 reviews
Rating 2 - Terrible. 0 out of 70 reviews

9.0/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great week! As a group of 14 adults there was plenty of room for everyone to spread out! The big kitchen was great! And of course having 3 fridges was a huge bonus. The ice maker was probably every ones favorite thing!
Stayed 7 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
GREAT layout for multi generation family.We had 15 people from 5 months (brought 2 pack n plays) to 76 years, from 3 states.Walkable to most of Dewey Beach.So convenient to beach, & pool was enjoyed by all 5 kids.Everyone wants the same house in the future.
Stayed 7 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
Great location. We had a few problems but Samantha was great to work with to try to get them corrected.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great home and perfect location. Steps from the beach and walkable to both Dewey and Rehoboth.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice property and well maintained.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Great Beach House

The location of the property to the beach and it being
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

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!
Stayed 4 nights in Feb 2019
Verified review

10/10 Excellent

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

Perfect for big group and multi-generational family vacation

The location and amenities are amazing! Samanatha was
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

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

Review of 10 chicAgo dewey beach delaware

Beautiful property in a great location
Stayed 7 nights in Jul 2022
Verified review

10/10 Excellent

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

Fabulous

This house was fabulous! Would definitely stay again.
Stayed 7 nights in Sep 2021
Response from VrboOwner on 11 October 2021
Thanks for your review
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 1 February 2024
Thanks
Verified review

10/10 Excellent

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

Perfect for Large Family Vacation

10 Chicago is a well appointed home that accommodates a large family. Steps from the beach with a pool too - something for everyone!
Stayed 7 nights in Aug 2021
Response from VrboOwner on 16 August 2021
Thanks or your nice review. We are certainly pleased and honored to have you as a guest in our house and will always do aur best to make your stay joyfull Thanks again and God Bless Fayez Helmi
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

family vacation

awesome
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
All as represented. Check in was easy. All requests accommodated immediately.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

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

Can’t beat the location

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!
Stayed 7 nights in Aug 2021
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

Family Beach Vacation

22 of us. Plenty of room, plenty of kitchen, plenty of dining space great pool for the kids. Samantha the property manager is A plus responsive.
Stayed 7 nights in Jul 2022
Response from VrboOwner on 14 July 2022
Thanks for your review
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

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
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