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Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home

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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!
Beautiful spaces to gather and make memories.
Spacious and open with lots of natural light! Dining table seats 10.
The front living area is filled with natural light and a cozy space to sit, enjoy a movie, or plan your day. Books, a DVD player and lots of DVDs if you don't feel like signing into your streaming services.
Great spot for morning coffee and watching the house stir awake.

Reviews

9.8 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 122200 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Dewey Beach, DE
  • Place, Fifer Orchards Local-Fresh Market - Dewey Beach
    ‪1 min walk‬
  • Place, Dewey Beach
    ‪5 min walk‬
  • Place, Bottle & Cork
    ‪9 min walk‬
  • Airport, Georgetown, DE (GED-Sussex County)
    ‪27 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

Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home

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 12 guests, the main level features a cozy living room, a kitchen overlooking 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. Please note that the VRBO service fee is charged separately by VRBO and is not imposed by the Host. As a result, your credit card will reflect two separate charges: one from VRBO for the service fee and one from the Host for the rental charges. The VRBO service fee will not appear on the Rental Agreement. Delaware Accommodations Intermediary #2024713094

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Spectacular pet friendly house walk to beach w/ocean views, private pool
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  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (4 reviews)
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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
High-risk rentals and special events are strictly prohibited at this property. This includes bachelor parties, senior weeks, and large groups.

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. The area's natural beauty can be seen at Rehoboth Beach and Lewes Beach. 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.
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Map
Dewey Beach, DE

What's nearby

  • Fifer Orchards Local-Fresh Market - Dewey Beach - 1 min walk - 0.0 km
  • Dewey Beach - 5 min walk - 0.4 km
  • Silver Lake - 6 min walk - 0.6 km
  • Bottle & Cork - 9 min walk - 0.8 km
  • Rehoboth Beach - 2 min drive - 1.1 km

Getting around

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

Restaurants

  • ‪The Starboard - ‬8 min walk
  • ‪Woody's Dewey Beach - ‬9 min walk
  • ‪Dewey Beer Co. - ‬7 min walk
  • ‪Grotto Pizza - ‬16 min walk
  • ‪Starboard Claw - ‬9 min walk

Frequently asked questions

Does Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home have a pool?

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

How much does it cost to stay at Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home?

As of 15 Mar, 2026, prices found for a 1-night stay for 2 adults at Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home on 17 May, 2026 start from S$1,155, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home?

On-site parking is available at the property.

What time is check-in at Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home?

Check-in begins at 3:00 PM.

What time is check-out at Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home?

Checkout is at 10:00 AM.

Where is Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home located?

Located in Rehoboth by the Sea, this holiday home is steps away from Fifer Orchards Local-Fresh Market - Dewey Beach and East of Maui. Dewey Beach and Silver Lake are also within 10 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. 9 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 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

John T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and comfortable with great pool and close proximity to Dewey Beach and restaurants.
Stayed 7 nights in Jul 2025

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

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

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

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

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

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

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

10/10 Excellent

Elizabeth R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Sep 2025

About the host

Hosted by RE/MAX Realty

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