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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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
Property # 3957477vb
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. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Fifer Orchards Local-Fresh Market - Dewey Beach - 1 min walk - 0.0 km
Dewey Beach - 5 min walk - 0.4 km
Silver Lake - 8 min walk - 0.7 km
Bottle & Cork - 9 min walk - 0.8 km
Rehoboth Beach - 3 min drive - 2.1 km
Getting around
Georgetown, DE (GED-Sussex County) - 30 min drive
Restaurants
The Starboard - 8 min walk
Rehoboth Ale House - 8 min walk
Woody's Dewey Beach - 9 min walk
Dewey Beer Co. - 7 min walk
Dewey Beach Country Club - 11 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.
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 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.
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!!
Allison M.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 12 July 2025
Hi Allison - Thanks for much for writing us a review. We are so delighted that you and your family loved your stay at this beautiful home. We hope you had time to enjoy the pool to cool off and relax after a day at the beach. We hope you will join us again next summer for your family vacation !
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!!
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.
Marilyn S.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 5 July 2025
Hi Marilyn - It's so nice to hear that you and your family had a wonderful vacation at this lovely home. The pool is always a big hit and with it being so hot......well how refreshing ! We hope that you will visit with us again next summer !
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!!
Janet K.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 21 September 2024
Hi Janet - Its so nice to hear you enjoyed this wonderful home at the beach. Charming and spacious for sure ! We hope you and your family will be able to join us again next summer
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.
Bridget M.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 4 September 2024
Hi Bridget - Thank you for taking the time to write us a review. We are so delighted that you enjoyed the house. It really is a wonderful place to stay. A pool is always a plus ! We hope you will be able to visit with us again next summer !
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.
Rick J.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 29 July 2025
Hi Rick - Thank you for taking the time to share your comments with us. We will definitely look into the charging cables availability issue. We are happy to hear you enjoyed your stay at this wonderful home and hope had time to enjoy the pool too.
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!
Thomas R.
Stayed 7 nights in Jun 2024
Response from VrboOwner on 24 June 2024
Hi Thomas - Thank you for taking the time to write us a review. We will check out the description and change as needed. We are delighted that you enjoyed this wonderful home, pool and all it offers. What a gem! Be sure to visit with us again