The Pines holiday rentals
We found 875 holiday rentals — enter your dates for availability
Discover a selection of 52 homes and other holiday rentals in The Pines that are perfect for your trip. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as Wi-Fi and parking. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts – The Pines
Showing deals for:25 Dec - 1 Jan

Exceptional
(37 reviews)
It's time to book summer of 2026! Book now before all summer weeks are full!
Rehoboth Beach
AU$11,384
for 7 nights, 1 home
AU$1,626 per night
includes taxes & fees

Exceptional
(37 reviews)
CasaCottage: 1 Block to Beach, Sleeps 14, Parking for 4 Cars!
Rehoboth Beach
AU$6,301
for 7 nights, 1 cottage
AU$900 per night
includes taxes & fees

Exceptional
(46 reviews)
Renovated 5BR: 1 Block to Ocean & Boardwalk + Parking for 4 cars + Sleeps 17!
Rehoboth Beach
AU$9,099
for 7 nights, 1 home
AU$1,300 per night
includes taxes & fees

Exceptional
(85 reviews)
Lakefront 3 bedroom townhouse in quiet community with pool
Rehoboth Beach
AU$4,039
for 7 nights, 1 home
AU$577 per night
includes taxes & fees

Exceptional
(28 reviews)
ONE SUMMER WEEK LEFT FOR BOOKING! INQUIRE NOW!
Rehoboth Beach
AU$20,911
for 7 nights, 1 home
AU$2,987 per night
includes taxes & fees

Exceptional
(30 reviews)
Great Rehoboth Beach House - Spacious and Well Appointed Sleeps 10
Rehoboth Beach
AU$5,683
for 7 nights, 1 home
AU$812 per night
includes taxes & fees

Wonderful
(28 reviews)
Only 1.5 Blocks To Ocean, 1-3 blocks of restaurants, shops, bars. Come enjoy!
Rehoboth Beach
AU$6,855
for 7 nights, 1 home
AU$979 per night
includes taxes & fees

Exceptional
(54 reviews)
Coastal Beach House with Pool Access - with Linens - 2 Kings, 1 Queen, 3 Twins
Rehoboth Beach
AU$2,739
for 7 nights, 1 home
AU$391 per night
includes taxes & fees

Exceptional
(91 reviews)
Amazing single family home, biking distance to the beach!
Rehoboth Beach
AU$4,460
for 7 nights, 1 home
AU$637 per night
includes taxes & fees

Exceptional
(62 reviews)
Refreshed for 2026: 3BR Rehoboth Beach Townhome
Rehoboth Beach
AU$2,385
for 7 nights, 1 home
AU$341 per night
includes taxes & fees

Exceptional
(49 reviews)
5 Blocks to Beach, Heated Pool, Parking, Two Master Suites - Full Townhouse
Rehoboth Beach
AU$1,977
for 7 nights, 1 home
AU$282 per night
includes taxes & fees

Wonderful
(28 reviews)
Convenient Rehoboth Beach in-town location
Rehoboth Beach
AU$4,819
for 7 nights, 1 apartment
AU$688 per night
includes taxes & fees

Exceptional
(14 reviews)
Beautiful Penthouse Condo with Community Pool & Tennis Courts
Rehoboth Beach
AU$6,461
for 7 nights, 1 apartment
AU$923 per night
includes taxes & fees

Exceptional
(64 reviews)
One bedroom Condo overlooking beach, Sept Weeks available with off season prices
Rehoboth Beach
AU$2,363
for 7 nights, 1 apartment
AU$338 per night
includes taxes & fees

Exceptional
(44 reviews)
Penthouse- Rehoboth Beach -3 Bedroom with private deck
Rehoboth Beach
AU$4,383
for 7 nights, 1 apartment
AU$626 per night
includes taxes & fees

Exceptional
(51 reviews)
Spacious House - Close to Rehoboth Boardwalk & Beaches - Porch, Bikes & Parking
Rehoboth Beach
AU$5,779
for 7 nights, 1 home
AU$826 per night
includes taxes & fees

Exceptional
(17 reviews)
CasaJunior: 1 Block to Beach, Full Kitchen, Onsite Parking, Linens Included!
Rehoboth Beach
AU$1,965
for 7 nights, 1 apartment
AU$281 per night
includes taxes & fees

Exceptional
(78 reviews)
2 Bed 2 Bath Condo In a Fantastic Location
Rehoboth Beach
AU$872
for 7 nights, 1 apartment
AU$125 per night
includes taxes & fees

Exceptional
(107 reviews)
Executive Townhome featured on A&E’s Vacation Home Potential Feb 2019!
Rehoboth Beach
AU$2,453
for 7 nights, 1 home
AU$350 per night
includes taxes & fees

Exceptional
(27 reviews)
Beach Modern Living Completely Remodeled Townhome
Rehoboth Beach
AU$2,235
for 7 nights, 1 home
AU$319 per night
includes taxes & fees

Wonderful
(32 reviews)
Rehoboth Ave Apartment - 2 blocks from the beach- In the heart of Rehoboth Beach
Rehoboth Beach
AU$2,392
for 7 nights, 1 apartment
AU$342 per night
includes taxes & fees

Exceptional
(36 reviews)
Penthouse 2 Blocks from Ocean/ 2 bedroom w/Private deck overlooking Rehoboth Ave
Rehoboth Beach
AU$5,386
for 7 nights, 1 apartment
AU$769 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Pines

Stunning Ocean Views! Beautiful 5BR Home in North Rehoboth Beach
Sleeps 10 · 5 bedrooms · 4+ bathrooms

11 Henlopen Ave. – Spacious Ocean-Block Retreat on the North End of Rehoboth Beach!
Sleeps 14 · 6 bedrooms · 4 bathrooms

Family Beach House Steps to Beach Sleeps 10
Sleeps 10 · 5 bedrooms · 2 bathrooms

PERFECT IN "THE PINES"- Walk to Beach, Shops & Restaurants-134 Henlopen Ave
Sleeps 7 · 4 bedrooms · 2 bathrooms

Classic 1920s oceanfront home & cottage with AC, bikes, grill - walk to beach
Sleeps 12 · 7 bedrooms · 6 bathrooms

"OLD REHOBOTH CHARM" - 1ST OCEAN BLOCK! Dog Friendly! Mini-Weeks!-31 Park Ave
Sleeps 10 · 4 bedrooms · 3 bathrooms
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit The Pines for a holiday rental?
The most popular time to visit The Pines is in November when the area transforms into a beautiful autumn retreat. This month offers a lovely balance of pleasant weather and stunning fall foliage, superb for those seeking scenic strolls and outdoor activities.While the peak season runs from May to July, characterised by vibrant summer festivals and warm temperatures, November provides a unique charm with milder conditions (around 5 to 15 degrees Celsius). This makes it an ideal time for comfortable exploration, whether you're wandering through local parks or enjoying a leisurely bike ride along the picturesque trails.For travellers looking for more budget-friendly options, October is a wonderful time to consider. Although it falls into the low season, October still offers pleasant temperatures and fewer crowds, allowing for a more relaxed experience while still enjoying the beauty of the changing leaves.Ultimately, your choice of when to visit The Pines should reflect your preferences—whether you're drawn to the lively summer atmosphere or the tranquil beauty of a fall getaway.
What are the top attractions in The Pines, Delaware, United States of America?
In The Pines, Delaware, visitors can enjoy a tranquil retreat surrounded by nature. The area is known for its proximity to beautiful beaches, particularly the nearby Rehoboth Beach, which offers a lively boardwalk, charming shops, and a variety of dining options. For those interested in outdoor activities, Cape Henlopen State Park, located just a short drive away, features scenic trails, picnic areas, and opportunities for birdwatching and water sports.Additionally, the quaint town of Lewes, not far from The Pines, boasts historical sites such as the Lewes Historical Society and the picturesque Lewes Beach, making it an attractive destination for day trips.
Are all fees included in the The Pines holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any The Pines holiday homes with parking?
Stayz offers a wide selection of holiday homes in The Pines with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for The Pines holiday homes?
You can find great discounts on holiday homes in The Pines on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my The Pines holiday home booking on Stayz?
To find The Pines holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in The Pines?
A long-stay holiday home in The Pines is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a The Pines holiday home?
Book your The Pines holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in The Pines?
Prices for holiday homes in The Pines vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in The Pines to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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