Rockland Holiday Rentals

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Our top choices for Rockland holiday rentals

8.8 out of 10, Excellent, (3)
"Was a great location and quite. The host was wonderful and helpful as I had an issue with my cat and he helped without hesitation. My cat and myself felt very comfortable and safe. Will definitely book again when I am in the area visiting my family."
United States
Mary S.
The price is AU$218
includes taxes & fees
3 Jan - 4 Jan 2026
Charming 1-Bedroom Basement Apartment with AC, WiFi in lovely Lansdowne
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is AU$247
includes taxes & fees
4 Jan - 5 Jan 2026
Summer Rustic Camping with AC and King Bed
10.0 out of 10, Exceptional, (11)
"Loved the property, had everything we needed and more.Plush towels, comfortable bed, wonderful environment filled with really cool art. "
United States
Valerie H.
The price is AU$250
includes taxes & fees
10 Jan - 11 Jan 2026
Welcome to the Mushroom Capital of the World!
10.0 out of 10, Exceptional, (195)
"Great time and friendly people "
United States
Karl
The price is AU$301
includes taxes & fees
3 Jan - 4 Jan 2026
Stylish Private Suite in the heart of Brandywine Valley
3.0 star property
The price is AU$461
includes taxes & fees
5 Jan - 6 Jan 2026
Walkable Neighborhood: Updated Morton Home!

Holiday Home in Collingdale

The Airport Lodge - 10 mins from Airport
10.0 out of 10, Exceptional, (9)
"Very nice accomodations, easy communication. Hope to be back soon!"
United States
Gina
The price is AU$193
includes taxes & fees
4 Jan - 5 Jan 2026
The Airport Lodge - 10 mins from Airport

Holiday Home in Darby

Basement Retreat by the Airport
8.0 out of 10, Very good, (1)
The price is AU$237
includes taxes & fees
2 Jan - 3 Jan 2026
Basement Retreat by the Airport

Holiday Home in Kennett Square

Underground Railroad Barn
9.8 out of 10, Exceptional, (30)
"Great little gem! Convenient location and a nice yard for the dog to play."
United States
Joanne S.
The price is AU$472
includes taxes & fees
4 Jan - 5 Jan 2026
Underground Railroad Barn
10.0 out of 10, Exceptional, (16)
"Our stay was perfect! We had a wonderful time with family celebrating our daughter's UD graduation."
United States
Heidi Z.
The price is AU$672
includes taxes & fees
5 Jan - 6 Jan 2026
Thunder Hill Retreat - Spacious/Deck/Hot tub
10.0 out of 10, Exceptional, (37)
"Beautiful "
United States
Dawn M.
The price is AU$670
includes taxes & fees
1 Jan - 2 Jan 2026
Charming Carriage House in the Heart of Kennett
10.0 out of 10, Exceptional, (3)
"Me and my family decided to stay over the weekend to travel around Philly and I can say that he is a great host! The house looks exactly like the pictures! Great communication, I would definitely book again! "
United States
Ciara R.
The price is AU$359
includes taxes & fees
29 Dec - 30 Dec
ComfiNook Retreat- 3BR Near PHL Airport + Parking + WiFi + AC

Apartment in Bear

Cozy loft above ink shop
9.6 out of 10, Exceptional, (5)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
United States
Krystle M.
The price is AU$176
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy loft above ink shop
8.6 out of 10, Excellent, (17)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is AU$263
includes taxes & fees
3 Jan - 4 Jan 2026
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Holiday Home in Downtown Wilmington

Private townhouse near downtown and state park
9.4 out of 10, Exceptional, (12)
"Great little spot in a perfect location for us"
United States
j m.
The price is AU$427
includes taxes & fees
29 Dec - 30 Dec
Private townhouse near downtown and state park
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$514
includes taxes & fees
1 Jan - 2 Jan 2026
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
2.0 star property
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is AU$545
includes taxes & fees
29 Dec - 30 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning
8.0 out of 10, Very good, (15)
"Great location with character! Host was friendly and communicated well."
United States
Ross G.
The price is AU$705
includes taxes & fees
8 Jan - 9 Jan 2026
Kennett Square, Near Longwood Gardens & Downtown
9.6 out of 10, Exceptional, (21)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is AU$505
includes taxes & fees
30 Dec - 31 Dec
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
8.4 out of 10, Very good, (33)
"Perfect overnight! Clean, quiet and comfortable- just what we needed!"
United States
Chelsea D.
2 Bedroom x 2 Bathroom in Malvern, PA

Holiday Home in Kennett Square

Underground Railroad 4 Bedroom Farmhouse
9.8 out of 10, Exceptional, (25)
"Very nice and clean! "
United States
Virginie M.
The price is AU$572
includes taxes & fees
1 Jan - 2 Jan 2026
Underground Railroad 4 Bedroom Farmhouse
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Rockland Hotel Reviews

Find out more about Rockland

Everything you need to know about Rockland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Rockland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Rockland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Rockland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Rockland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Rockland holiday rentals we have selected for you start as low as AU$188 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Rockland rentals

At Expedia, we put the best Rockland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Rockland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Rockland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Rockland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Rockland?

Yes, there are holiday rentals close to the most popular sights in Rockland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Rockland has to offer?

The Lodge at Cricklewood...where time melts away....: This holiday home rental outside of Rockland is located on a river, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Rockland?

While exploring the area, visit family-friendly sights like Kalmar Nyckel Museum and Shipyard, or get outside and enjoy nature at Brandywine Creek. Brandywine Creek State Park and Hagley Museum and Library are a couple of places you'll find in the wider area.

What’s a holiday rental in Rockland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Rockland. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.