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Entire home

10 bedrooms10 bathroomsSleeps 22

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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

Holiday home with kitchen, near Rehoboth Beach Boardwalk
This smoke-free holiday home features laundry facilities and gas grills. The holiday home has 10 bedrooms and offers a sofa bed and a balcony. Guests can enjoy a fireplace, and other amenities include a kitchen with a fridge and an oven.
Air-conditioned accommodation at this holiday home offers fireplaces and coffee/tea makers. Rooms open to balconies. This accommodation is furnished with sofa beds and kitchen islands. Flat-screen televisions are featured in guestrooms.

Kitchens offer fridges, stovetops, microwaves and dishwashers. Additionally, rooms include a hairdryer and an iron/ironing board.

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)

Similar properties

Beach nearby

FREE CHEF OR BONFIRE WITH MINIMUM 3 NIGHT STAY! ROOFTOP POOL & HOT TUB ALL YEAR!

  • Sea view
  • Pool
  • Hot tub
  • Kitchen
9.8 out of 10, Exceptional, 116 reviews
FREE CHEF OR BONFIRE WITH MINIMUM 3 NIGHT STAY! ROOFTOP POOL & HOT TUB ALL YEAR!

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 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

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

Property is also known as

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

About the area

Map
Dewey Beach, DE

What's nearby

  • Dewey Beach - 1 min walk - 0.0 km
  • Rehoboth Beach - 2 min drive - 1.4 km
  • Rehoboth Beach Boardwalk - 4 min drive - 2.8 km
  • Funland - 4 min drive - 2.8 km
  • Tanger Outlets - 5 min drive - 5.2 km

Getting around

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

Restaurants

  • ‪The Starboard - ‬8 min walk
  • ‪Woody's Dewey Beach - ‬8 min walk
  • ‪Dewey Beer Co. - ‬7 min walk
  • ‪Starboard Claw - ‬9 min walk
  • ‪Jimmy's Grille - ‬9 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.

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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Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 54 out of 62 reviews
Rating 8 - Good. 7 out of 62 reviews
Rating 6 - Okay. 1 out of 62 reviews
Rating 4 - Poor. 0 out of 62 reviews
Rating 2 - Terrible. 0 out of 62 reviews

9.0/10

Cleanliness

Reviews

10/10 Excellent

Beth H.

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

10/10 Excellent

Samantha G.

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

10/10 Excellent

Keith S.

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

10/10 Excellent

Lorri G.

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

10/10 Excellent

Ben G.

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

10/10 Excellent

richard k.

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

10/10 Excellent

Jonathan T.

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

10/10 Excellent

Bruce H.

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

10/10 Excellent

susan b.

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

family vacation

awesome
Stayed 7 nights in Jun 2024

10/10 Excellent

Samantha G.

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

10/10 Excellent

Samantha G.

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

10/10 Excellent

Carol C.

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

10 Chicago is a perfect 10!

Our large extended family truly enjoyed all this home had to offer - great pool with plenty of outdoor seating & Weber grill, just steps to the beach, beautifully furnished, wonderful gourmet kitchen and plenty of space for all to enjoy! We can’t wait to come back.
Stayed 6 nights in Jul 2020

10/10 Excellent

Valerie H.

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

10/10 Excellent

Liz G.

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

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

8/10 Good

Mary A.

Liked: Communication, location, listing accuracy
Disliked: Check-in

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

Mary A.

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

8/10 Good

Valerie H.

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

Third time's a charm

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.
Stayed 7 nights in Jun 2025

10/10 Excellent

Anita T.

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

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, 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

10/10 Excellent

margo H.

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

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.

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

10/10 Excellent

Linda I.

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

10/10 Excellent

Janice S.

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

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, check-in, communication, location, listing accuracy

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?

Liked: Check-in, communication, location

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