Street Holiday Rentals

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Holiday Rentals in Street

Cottage in Willow Street

10.0 out of 10, Exceptional, (209)
"A superb property - exceptionally clean and very well equipped with everything you could possibly need! The location was perfect for exploring the local area and further afield and the hot tub was an added bonus for relaxing in the evenings."
United Kingdom
Gillian P.
Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

Cottage in Conestoga

9.8 out of 10, Exceptional, (124)
"We loved staying in this cottage. It is in a quiet location. Loved the hot tub. "
United States
Anonymous traveller
The price is AU$526
includes taxes & fees
8 Dec - 9 Dec
Restful and Quaint Cottage

Cottage in Port Deposit

10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is AU$319
includes taxes & fees
8 Dec - 9 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Holiday Home in Willow Street

9.8 out of 10, Exceptional, (270)
"Very comfortable and cozy place that stay! "
United States
Terri H.
The price is AU$430
includes taxes & fees
8 Dec - 9 Dec
River Rock Room at Muse House: Secluded Luxury in horse country.

Holiday Home in Perryville

10.0 out of 10, Exceptional, (20)
"Great waterfront home with sunset views! Plenty of space for our group, very clean, and the hot tub was a perfect bonus. Peaceful, relaxing, and just as described. We’d definitely come back!"
United States
Kaylyn G.
Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront

Holiday Home in Abingdon

8.4 out of 10, Very good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is AU$1,265
includes taxes & fees
8 Dec - 9 Dec
Luxury Waterfront Home Built for Entertaining!

Holiday Home in Drumore

10.0 out of 10, Exceptional, (262)
"The house was just as described and the property owners were very nice and accommodating."
United States
Deanna J.
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

Cabin in Fawn Grove

9.6 out of 10, Exceptional, (12)
"Two night stay was very nice. Great living, kitchen and bedroom spaces. Very quiet area."
United States
Rene S.
The price is AU$521
includes taxes & fees
8 Dec - 9 Dec
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Cottage in Strasburg

10.0 out of 10, Exceptional, (319)
"This place was amazing and beyond peaceful and relaxing. Will definitely pick this place again when traveling back to Pennsylvania. "
United States
Brandi B.
COMPLETELY RESTORED 1700's HOME SURROUNDED BY FARMLAND

Holiday Home in New Providence

10.0 out of 10, Exceptional, (49)
"Add a wonderful stay with my family."
United States
Sheryl P.
Historic Stone House on Beaver Creek

Holiday Home in Pequea

9.8 out of 10, Exceptional, (284)
"We loved the spacious rooms. We used the hot tub every night. The view from this property is so serene and relaxing. 100% recommend!"
United States
Carrie D.
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

Holiday Home in Pequea

10.0 out of 10, Exceptional, (142)
"Beautiful house and property that my extended family consisting of 14 people (ranging from ages 8 to 81) thoroughly enjoyed. Just bring your own groceries and the kitchen is stocked with everything else anyone could need. My brother-in-law brought his own kayaks and body boards so we could explore the river and tiny island across from the property. Brian was a great host; always available to answer all of our questions (and we had a lot) about the house and things to do in the area."
United States
Nicole K.
Waters Edge

Holiday Home in Elkton

9.8 out of 10, Exceptional, (44)
"This was our second time staying here and we really love it! It has everything needed and is very close &convenient to any outing we did, The house layout works great for our group of six. Already planning our next trip!! "
United States
Susan G.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

Holiday Home in Perryville

9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is AU$915
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

Holiday Home in Lutherville

9.4 out of 10, Exceptional, (8)
"We loved the modern, clean vibe of the house. It was very conveniently located near the golf courses and restaurants. Would recommend this Vrbo highly to others."
United States
diane h.
The price is AU$1,031
includes taxes & fees
9 Dec - 10 Dec
Inviting Escape Bursting w/ Elegance & Style

Holiday Home in Pequea

10.0 out of 10, Exceptional, (253)
"Terrific place and lovely setting. Bald eagle sightings were a real bonus!"
United States
bobbye d.
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

Holiday Home in Bel Air

10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
The price is AU$429
includes taxes & fees
5 Jan - 6 Jan 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Holiday Home in Holtwood

2.0 star property
10.0 out of 10, Exceptional, (26)
"Whole place was top notch! "
United States
Kelly P.
A working horse farm in Southern Lanc Co., nestled in Amish country.

Holiday Home in Nottingham

2.0 star property
The price is AU$799
includes taxes & fees
14 Dec - 15 Dec
Close to Hospital & White Marsh! Rosedale Townhome

Holiday Home in Pequea

10.0 out of 10, Exceptional, (2)
"I had a great time and the place was very beautiful and peaceful "
United States
Brittany R.
The price is AU$666
includes taxes & fees
8 Dec - 9 Dec
Enola Trail Getaway *bikes*rural
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 Street Hotel Reviews

Find out more about Street

Everything you need to know about Street 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 Street 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 Street holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Street holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Street. 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 Street 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 Street holiday rentals we have selected for you start as low as AU$319 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Street rentals

At Expedia, we put the best Street 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 Street 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 Street 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 Street. 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 Street?

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

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

Upper Chesapeake Bay 5 bedroom, 3 bath, Hot Tub, Waterfront: This holiday home rental outside of Street is located on a river, and has a patio, a garden 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. You can relax into your holiday with a selection of games and 1 hot tub.

What can I see and do in Street?

While exploring the area, visit family-friendly sights like Guppy Gulch Quarry, or get outside and enjoy nature at Ladew Topiary Gardens. Rocks State Park and Palmer State Park are other places to visit while you're in town.

What’s a holiday rental in Street like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Street. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.