New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!
Welcome to Osprey Pines at 116 Chesapeake, the classic Dewey Beach coastal cottage you remember with every modern amenity and 2024 upgrades! One of the few remaining classic cottages in quiet and serene yet convenient Rehoboth by the Sea, this architectural gem is just 1.5 blocks from the beach, walking/biking distance to both downtown Dewey Beach and Rehoboth Beach, pet friendly, offers off-street parking for 4 cars + 2 parking passes and has multiple inside and outside gathering spaces that allow family and friends to spread out. The terrific north Dewey location offers everything you could want in a quiet yet convenient week at the beach.
Osprey Pines' outdoor amenities include a recently remodeled enclosed screened porch with ample seating and dining areas, large private side and rear decks with additional seating and dining areas, a gas grill for BBQs and a large outdoor shower. Inside, the front living, kitchen and dining areas offer ample open floor space to gather. 17' ceilings, floor-to-ceiling windows, large sliding glass doors opening to the screened porch and back deck and 9 skylights throughout the cottage bring the outside in, creating a very serene setting.
The cottage has 5 BRs, 3 Full BA, 2 Half BA and an outdoor shower. The front living room sofa is a Queen pull-out, allowing even more bed space. A large King primary bedroom and just-remodeled full bath with double vanity is located off the front living area. Heading through the breezeway you'll find a full bathroom off the hallway and a large den/sitting area with sliding door access to the large back deck. The den is yet another perfect place for watching TV, reading or family game night! There are 4 bedrooms off the breezeway, a King with full bath and sliding door access to the back deck, a Queen with en suite half bath, a Double/Twin bunk room with en suite half bath and direct access to the outside shower and a fourth smaller bunk room with two twin bunks that are absolutely perfect for your kiddos or teens. (Note, while the bunks are plenty comfortable for sleeping and the room includes large windows and a large closet, this room is smaller than the others).
For additional photos, visit @ospreypines on Instagram
116 Chesapeake isn't lacking in any way. You'll find it's the convenient and tranquil beach house rental you're looking for! And, Osprey Pines is pet friendly! Offering an fully enclosed yard. (1 dogs only / $300 pet fee.)
2024 Upgrades: The newly fenced yard means Fido can enjoy a safe and fun week at the beach Front King Primary BR - new paint in bedroom and remodeled bath, including new paint, fixtures and a double vanity. New front yard hardscaping now accommodates 4 off-street parking spaces
A linen package can be purchased for your stay. The cost of the linen package for one week's stay is $331.00.
Smoking / vaping is not permitted anywhere on the property.
Booking Restrictions: Weekly Rentals only May through September
All VRBO reservations are a booking request only until confirmed by Property Manager. You will be required to sign a Residential Lease Agreement and make your payment within the required deadlines provided or your booking request will be cancelled. As a property manager, we welcome “Special Event” rentals. All properties are individually owned and not all properties are available for “Special Event” rentals. Credit Card payments subject to 2% fee.
Bedding: 1 KING, 1 KING, 1 QUEEN, 1 DOUBLE + 1 TWIN BUNK, 1 BUNKROOM with 4 Twins. 1 QUEEN sofa pull-out in Living Room.
State of Delaware License # 2025701763
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Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space
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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 indicated that 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
About the area
Rehoboth Beach
Located in Rehoboth by the Sea, a neighbourhood in Rehoboth Beach, this holiday home is near a water park 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. Looking to get your feet wet? Kayaking, power boating and surfing/body boarding adventures can be found near the property.
Fifer Orchards Local-Fresh Market - Dewey Beach - 5 min walk - 0.4 km
Rehoboth Beach - 19 min walk - 1.6 km
Rehoboth Beach Boardwalk - 3 min drive - 2.4 km
Getting around
Georgetown, DE (GED-Sussex County) - 32 min drive
Restaurants
The Starboard - 14 min walk
Woody's Dewey Beach - 15 min walk
Rehoboth Ale House - 11 min walk
Dewey Beer Co. - 11 min walk
Dewey Beach Country Club - 16 min walk
Frequently asked questions
Is New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!?
As of 23 Apr 2026, prices found for a 1-night stay for 2 adults at New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach! on 27 June 2026 start from AU$1,647, 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.
How much is parking at New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!?
On-site parking is available at the property.
What time is check-in at New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!?
Check-in begins at 3:00 PM.
What time is check-out at New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!?
Checkout is at 10:00 AM.
Where is New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach! located?
Located in Rehoboth by the Sea, this holiday home is within 1 mi (2 km) of Silver Lake and Rehoboth Beach. Rehoboth Beach Boardwalk is 1.3 mi (2.1 km) away.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house was perfect for two families. Plenty of room with a great location. The property manager was very responsive and we really appreciated all of his help.
Shelby H.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 31 Aug 2024
As a managing company, your business is appreciated and valued! We are so very happy to hear your stay at the beach and hope to be welcoming you back next summer!
Our family enjoyed a week vacation at Rehoboth by the Sea. We had a toddler and a great-grandfather with us, and the one story set up worked very well. The kitchen was much better stocked than most rentals. The house was in a quiet neighborhood and close to a very nice beach. The layout of the house was a little unusual with the sunroom central to traffic flow, and hall windows in the bedrooms decreased privacy in two of the bedrooms. (There are curtains on the windows though) There were several gathering areas in the house which we loved. The outside sitting areas were nice in the evening. Overall we loved this charming home!
Joan H.
Stayed 7 nights in Jul 2023
From a partner site
10/10 Excellent
Thomas B.
19 Sept 2023
Perfect Vacation!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Our group of 8 had a great stay at 116 Chesapeake. The house location is spectacular - close to the beach and close to all the action of Dewey & Rehoboth, yet on a quiet, serene street. We were able to park our cars and ride our bikes to everything. The house is one of the original "California" style cottages in Rehoboth-By-The-Sea, but it has been thoroughly updated (with an addition) to today's standards. The layout of the house is great with plenty of bedrooms & ensuite baths, plus three group spaces. Plenty of space for adults and kids to spread out. We enjoyed eating our meals at the table in the screened in porch, as well as relaxing on the comfortable furniture. 116 Chesapeake is a great house & great location - we wouldn't hesitate to stay there again or recommend it to friends.
Thomas B.
From a partner site
10/10 Excellent
Robert L.
5 Sept 2023
2023 Summer vacation
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We had an amazing time in Delaware. The house was perfect. More than enough room for the 7 of us that stayed. The screened in room was great at night to sit and have a couple of drinks. Location was great. Block away from the beach. Definitely coming back next year. Bill was great too.
Robert L.
From a partner site
10/10 Excellent
Libby S.
8 Aug 2023
The Perfect Beach House
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Our family has been going to Dewey/Rehoboth for more than 70 years and through 5 generations. Our parents and grandparents are gone now though never forgotten, but this year three generations shared this beautiful beach house and voted it “the best ever”. We do plan to return in 2024 as we continue the cherished tradition of spending beach time together in the Rehoboth/Dewey area.
Libby S.
About the host
Hosted by Carla L. Hall Riddle, REALTOR
Languages:
English
Premier Host
They consistently provide great experiences for their guests