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Private Pool Dewey Beach House Two Blocks from Beach!

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Welcome to 118 Chicago Street. Located just a block and a half from the ocean with it's own private pool!
Walk straight from the beach to your outdoor shower and dive into your private oasis.
Lovely Front Porch and Plenty of Private Parking. You will find an EV Charging plug on the front porch. Bring your own, or let us know if you would like to borrow our charging unit so we can leave it out for you.
Loads of natural light through slider doors leading to the pool.
The spacious kitchen is fully equiped.

Reviews

9.8 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 12204.4 sq m

Popular amenities

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

Explore the area

Map
Dewey Beach, DE
  • Dewey Beach
    ‪5 min walk‬
  • Bottle & Cork
    ‪9 min walk‬
  • Rehoboth Beach Boardwalk
    ‪3 min drive‬
  • Georgetown, DE (GED-Sussex County)
    ‪31 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom #1

1 Double Bed

Bedroom #2

1 King Bed

Bedroom #3

2 Single Beds

Bedroom #4

4 Single Beds

Bedroom #5

1 King Bed and 1 Queen Bed

3 bathrooms

Bathroom #1

Bathtub or shower · Toilet

Bathroom #2

Toilet · Shower only

Bathroom #3

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Dining area

About this property

Private Pool Dewey Beach House Two Blocks from Beach!

Welcome to 118 Chicago Street, a charming single-family home nestled in the Rehoboth By the Sea community, just 1.5 blocks from the heart of Dewey Beach. This coastal retreat offers the ideal blend of comfort and convenience, placing you within walking distance of Dewey's vibrant nightlife, exciting water sports, and the Jolly Trolley, which provides easy access to the boardwalk, shops, and dining in nearby Rehoboth Beach.
Recently upgraded, the home features a private heated pool, a spacious rear patio with ample seating, a fire pit, a gas grill, and an outdoor shower with a private changing room. Comfortably accommodating twelve guests, the main level features a cozy living room, a kitchen that overlooks the pool area, one bedroom, a hall bath, and a dining space ideal for family meals. The second floor features four generously sized bedrooms and two additional bathrooms, offering ample space for everyone.
Set on a quiet, family-friendly street lined with mature trees and lush landscaping, the home also includes off-street parking for six vehicles and a Universal 220/240 EV cable stored in the laundry room for guest use. The private pool is open from May through October. Additional amenities include ceiling fans, Wi-Fi, a washer and dryer, and accommodations for two dogs with a pet fee (no cats permitted). Linens are not supplied, but rental packages are available for your convenience.
For a memorable beach getaway in the heart of Dewey Beach, this home offers an unbeatable combination of location, comfort, and amenities. Delaware Accommodations Intermediary #2024713094.. Damage Waiver Information
Your reservation includes a nightly Damage Waiver fee (plus tax, if applicable), which covers accidental damage to the property or its contents—such as furniture, appliances, or fixtures—up to $3,000, provided the incident is reported to the host before checkout.
This fee replaces the need for a traditional security deposit, offering peace of mind during your stay.
For full details, please refer to the "Review the rental agreement" link available on the checkout page.

Property manager

RE/MAX Realty
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted
This property is unavailable for special event reservations (senior week/bachelorette parties/bachelor parties/etc.).
A pet addendum and pet fee are required to bring a pet.

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Dewey Beach

Located in Rehoboth by the Sea, a neighbourhood in Dewey Beach, this holiday home is near theme parks and near the beach. 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. Fifer Orchards Local-Fresh Market - Dewey Beach and East of Maui are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Dewey Beach, DE

What's nearby

  • Dewey Beach - 5 min walk - 0.4 km
  • Bottle & Cork - 9 min walk - 0.8 km
  • Rehoboth Beach - 2 min drive - 1.1 km
  • Rehoboth Beach Boardwalk - 3 min drive - 2.1 km
  • Tanger Outlets - 4 min drive - 4.9 km

Getting around

  • Georgetown, DE (GED-Sussex County) - 30 min drive

Restaurants

  • ‪Rusty Rudder - ‬2 min drive
  • ‪Dewey Beer Company - ‬7 min walk
  • ‪Woody's Dewey Beach - ‬9 min walk
  • ‪Nalu Surf Bar - ‬16 min walk
  • ‪Wings To Go - ‬10 min walk

Frequently asked questions

Does Private Pool Dewey Beach House Two Blocks from Beach! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Private Pool Dewey Beach House Two Blocks from Beach! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Private Pool Dewey Beach House Two Blocks from Beach!?

Check-in begins at 3:00 PM.

What time is check-out at Private Pool Dewey Beach House Two Blocks from Beach!?

Checkout is at 10:00 AM.

Where is Private Pool Dewey Beach House Two Blocks from Beach! located?

Located in Rehoboth by the Sea, this holiday home is steps from Fifer Orchards Local-Fresh Market - Dewey Beach and 1.7 mi (2.7 km) from Rehoboth Beach Boardwalk. East of Maui and Dewey Beach are also within 5 minutes.

Reviews

9.8

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

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.0/10

Listing accuracy

Reviews

10/10 Excellent

Allison M.

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

Great location! Excellent for families with kids!!

We stayed here with 8 adults and 4 children and everyone had a great time! We loved the proximity to the beach and Rehoboth!! The house was well-maintained and the perfect fit for our group. We would definitely stay here again!!
Stayed 7 nights in Jun 2025

10/10 Excellent

Marilyn S.

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

Location, location, location!

Fantastic location, walking distance to everything. Property mgr was exceptionally responsive to our needs. Pool was a hit sunce it was so hot and humid. We wete in it twice a day! Bedroooms comfortable and kitchen had all we needed for mesl prep.
Stayed 7 nights in Jun 2025

10/10 Excellent

Patricia D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was such a wonderful stay with our family. We loved the easy access to downtown Dewey or rehobeth. The pool was such a bonus for two little girls age 4 and 7. The house had anything and everything that we could have imagined. It was nicely decorated as well. Highly recommend!!
Stayed 4 nights in Jun 2025

10/10 Excellent

Dale B.

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

Family Vacation

Calm, peaceful location convenient to many activities. Space met the needs for all ages.
Stayed 7 nights in Sep 2024

10/10 Excellent

Rick J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
great for family vacation at beach.Couple comments:1. Linen package didn’t include one of the beds.2. Description said EV charging cable available upon request. It took some back and forth to get cable, and we were told owner was gonna change the description about cable availability. Personally, I think the charging cable is a selling point. We had two EV’s, and it was a selling point for us.
Stayed 7 nights in Jul 2025

10/10 Excellent

Janet K.

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

We had a wonderful time!

Thank you for sharing your lovely home with us! We all enjoyed the casual and relaxed spirit of this home. It was clean, well-equipped, spacious, and welcoming. Close to the beach and an adorable farm market with everything we needed. Lovely vacation!!
Stayed 7 nights in Aug 2024

10/10 Excellent

Bridget M.

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

Super

We stay at the beach every summer, first time with a pool. I was surprised at how wonderful it was to have a pool. Fun for the kids in the evening while we made dinner. There was plenty of sleeping space but it didn’t feel crowded. The house was very clean the the kitchen well stocked and the location could not have been better.
Stayed 7 nights in Aug 2024

8/10 Good

Thomas R.

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

Lovely & Peaceful!

The home is a perfect blend of beach cozy w/modern day comforts, convenience of location and your own pool! Really Love the location and easy walk to Fifer’s, the beach and into Dewey for lunches and dinners too. The only constructive feedback I’d give is to update the listing to properly reflect the home doesn’t have a Primary Bedroom w/En Suite. None of the five bedrooms has a bathroom directly or privately attached. For this Renter, w/Family and Friends invited, that distinction is very important prior to booking. It felt purposely misleading and having that prior knowledge would certainly help to avoid confusion and any arrival disappointments of future renters. Other than that PR mistake we loved the home. Thank You!
Stayed 7 nights in Jun 2024

About the host

Hosted by RE/MAX Realty

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Languages:

English

Premier Host

They consistently provide great experiences for their guests