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

Holiday home with kitchen, near Rehoboth Beach Boardwalk

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Stunning beachfront neighborhood with a variety of homes and a clear view of the ocean.
Enjoy cooking in this well-equipped kitchen with a granite countertop, stainless steel range hood, and dishwasher.
Relax in this stylish living room with a large sofa, wooden floor, and ceiling fan.
Relax on the balcony with a comfortable sofa set and enjoy the view.
Relax by the pool in a modern setting with a spacious balcony overlooking the area.

Reviews

9.8 out of 10
Exceptional

Entire home

10 bedrooms10 bathroomsSleeps 22

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer

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.

Add dates for prices

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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Beach nearby

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  • Pool
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9.8 out of 10, Exceptional, 112 reviews
2026 CALENDAR OPEN FOR BOOKING! FREE CHEF OR BONFIRE WITH MINIMUM 3 DAY STAY!

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

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 - 2.4 km
  • Funland - 4 min drive - 2.4 km
  • Tanger Outlets - 5 min drive - 5.2 km

Getting around

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

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.

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

9.8

Exceptional

Rating 10 - Excellent. 51 out of 58 reviews
Rating 8 - Good. 6 out of 58 reviews
Rating 6 - Okay. 1 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 0 out of 58 reviews

9.0/10

Cleanliness

Reviews

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

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

susan b.

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

family vacation

awesome
Stayed 7 nights in Jun 2024

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

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

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

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

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

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

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

Verified traveller

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

10/10 Excellent

Sandra D.

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

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

Guy T.

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

10/10 Excellent

Claudia N.

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

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

10/10 Excellent

Valerie H.

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

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

Nanci P.

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

Great Location, beautiful pool, fully equipped

This is a great house for a large family or group. All of the bedrooms are good. Several refrigerators, freezers, dishwashers and washer/dryers. Pool is terrific. Great air conditioning. Comfortable mattresses. If you are picky, it would be best to bring your own linens, blankets and pillows.
Stayed 7 nights in Jun 2022

8/10 Good

Cathleen M.

Liked: Check-in, communication, location, listing accuracy
Disliked: Cleanliness

Gather the Group!

This is a lovely rental property that answers the needs of many. We had a great time and enjoyed all this location and home had to offer. My only issue was the level of cleanliness. The property manager was very responsive to our feedback and requests and we stepped up to clean where needed. These rentals need a little TLC from time to time and as long as the owner/manager continue to maintain this property, this place is perfect for a large group, family gathering, or an escape for couples!
Stayed 7 nights in Jun 2022

10/10 Excellent

david f., Alexandria Virginia USA

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

I shall return

The proximity to the beach, the views from both decks, the room sizes, the well equipped kitchen with multiple refrigerators and cooking utensils make this an ideal house for a large family gathering . The house manager Samantha was a pleasure to work with and extremely helpful. The house is located about a 8 minute walk to Dewey's man drag and a 1 mile walk to Reheboth center of the boardwalk. If you have a dog less than 50 lbs, bring it as the beach is the best dog park early morning unitl 10 AM and after 5 PM. We had a great time!!!
Stayed 7 nights in Jun 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

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

10/10 Excellent

Manjula D., Maryland

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

Simply outstanding on all fronts!

This property is simply extraordinary in many ways. The location couldn't be perfect so close to the beach and the house is perfect for a large group with its 10 king-size bedrooms each with an attached bathroom. It made the lives of the 20 of us among 8 young families so easy. The amenities were excellent and the furniture and appliances were of very high quality and new. The pool was a great bonus, especially for our off-season visit. The complimentary beach chairs and gears came very handy. The best of all is the hospitality and kindness of the owner and the manager. The manager, Samantha, went above and beyond our expectations with prompt communication and flexibility. One of our families had left a personal item behind and Samantha was kind enough to find it and overnight it to the guest without any hesitation. We cannot recommend this place highly enough and very much hope to revisit in the future. As for feedback, the only recommendation would be to upgrade a bit of the house decorations (could do wonders to the already beautiful house) and increase the water temperature of the pool a bit higher for off-season. Overall, we had a memorable time and very much look forward to revisiting again soon.
Stayed 3 nights in Oct 2020

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