Entire home
New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!
Photo gallery for New Listing! Pet friendly, Rehoboth by the Sea home, 1.5 blocks to the beach!





Reviews
10 out of 10
Exceptional
5 bedrooms 3+ bathrooms Sleeps 12
Popular amenities
Explore the area

Dewey, DE
- Rehoboth Beach19 min walk
- Rehoboth Beach Boardwalk3 min drive
- Tanger Outlets4 min drive
- Georgetown, DE (GED-Sussex County)31 min drive
Rooms & beds
5 bedrooms (sleeps 12)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 Queen Bed
Bedroom 4
1 Double Bed and 1 Single Bunk Bed
Bedroom 5
2 Single Bunk Beds
3 bathrooms, 2 half bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Bathtub or shower · Toilet
Bathroom 3
Toilet · Shower only
Half Bathroom 4
Toilet
Half Bathroom 5
Toilet
Spaces
Deck or patio
Kitchen
Dining area
About this property
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
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
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Charming 4BR Cottage w/ Pool, 1 Block to Beach
Charming 4BR Cottage w/ Pool, 1 Block to Beach
- Pool
- Kitchen
- Pet-friendly
- Air conditioning
9.8 out of 10, (74 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
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 indicated that there is a smoke detector on the property
About the area
Rehoboth Beach
Located near the beach, this holiday home is in Rehoboth by the Sea, a neighbourhood in Rehoboth 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.

Dewey, DE
What's nearby
- Dewey Beach - 3 min walk - 0.3 km
- Rehoboth Beach - 19 min walk - 1.6 km
- Rehoboth Beach Boardwalk - 3 min drive - 1.7 km
- Funland - 3 min drive - 1.7 km
- Tanger Outlets - 4 min drive - 4.2 km
Getting around
Restaurants
- The Starboard - 14 min walk
- Woody's Dewey Beach - 15 min walk
- Dewey Beer Co. - 11 min walk
- Gary's Dewey Beach Grill / 38° - 14 min walk
- Starboard Raw - 14 min walk
Frequently asked questions
About the host
Hosted by Bill Mantyla

Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback