Pylesville Vacation Rentals

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Our top choices for Pylesville vacation rentals

Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub

Pennsy Ridge Hideaway: Relax in our centrally-located wooded retreat w/ hot tub
Willow Street
10.0 out of 10, Exceptional, (210)
"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

Restful and Quaint Cottage

Restful and Quaint Cottage
Conestoga
9.8 out of 10, Exceptional, (125)
"We loved staying in this cottage. It is in a quiet location. Loved the hot tub. "
United States
Anonymous traveler
$312 nightly
The price is $344
Dec 15 - Dec 16
Total with taxes and fees
Restful and Quaint Cottage

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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.
$196 nightly
The price is $207
Dec 15 - Dec 16
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

River Rock Room at Muse House: Secluded Luxury in horse country.

River Rock Room at Muse House: Secluded Luxury in horse country.
Willow Street
9.8 out of 10, Exceptional, (271)
"Very comfortable and cozy place that stay! "
United States
Terri H.
$256 nightly
The price is $283
Dec 14 - Dec 15
Total with taxes and fees
River Rock Room at Muse House: Secluded Luxury in horse country.

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
8.6 out of 10, Excellent, (7)
"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.
$784 nightly
The price is $831
Dec 14 - Dec 15
Total with taxes and fees
Luxury Waterfront Home Built for Entertaining!

Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
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!

Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.
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.
$313 nightly
The price is $346
Dec 13 - Dec 14
Total with taxes and fees
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Historic Stone House on Beaver Creek

Historic Stone House on Beaver Creek
New Providence
10.0 out of 10, Exceptional, (50)
"Add a wonderful stay with my family."
United States
Sheryl P.
Historic Stone House on Beaver Creek

LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
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

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
9.0 out of 10, Wonderful, (6)
"Pleasant stay"
United States
Yommali G.
Charming 2-bedroom house in Aberdeen with WiFi and AC

Waters Edge

Waters Edge
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

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
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

Historic Brickhouse Guest Home

Historic Brickhouse Guest Home
Refton
9.6 out of 10, Exceptional, (30)
"Clean quiet perfect place to stay…great coffee shop with fabulous breakfast menu and lunch"
United States
kim s.
Historic Brickhouse Guest Home

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace
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.
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

A working horse farm in Southern Lanc Co., nestled in Amish country.

A working horse farm in Southern Lanc Co., nestled in Amish country.
2.0 star property
Holtwood
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.

Winter Getaway|Hot tub|OUTDOOR SAUNA|Fireplace|Fire-pit|

Winter Getaway|Hot tub|OUTDOOR SAUNA|Fireplace|Fire-pit|
Willow Street
10.0 out of 10, Exceptional, (21)
"It was absolutely beautiful! The house is close to everything but also tucked away. The hot tub is an extra bonus. The host was great with checking in and making sure we were comfortable for our stay. Will definitely be staying here again."
United States
Katelyn C.
$327 nightly
The price is $345
Jan 8 - Jan 9, 2026
Total with taxes and fees
Winter Getaway|Hot tub|OUTDOOR SAUNA|Fireplace|Fire-pit|

Enola Trail Getaway *bikes*rural

Enola Trail Getaway *bikes*rural
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.
$396 nightly
The price is $437
Dec 16 - Dec 17
Total with taxes and fees
Enola Trail Getaway *bikes*rural

Comfortable and quiet 3-bedroom-walk to downtown

Comfortable and quiet 3-bedroom-walk to downtown
Havre de Grace
10.0 out of 10, Exceptional, (3)
"great stay"
United States
Randy S.
Comfortable and quiet 3-bedroom-walk to downtown

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
$200 nightly
The price is $212
Jan 5 - Jan 6, 2026
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom

Nature's Grove Cabin

Nature's Grove Cabin
Delta
10.0 out of 10, Exceptional, (5)
"Stayed over a few days while in the area for sons wedding. Was a cute and quite area to decompress from the hectic days of getting the wedding day ready!"
United States
Casey K.
Nature's Grove Cabin
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 Pylesville Hotel Reviews

Find out more about Pylesville

Everything you need to know about Pylesville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pylesville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Pylesville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pylesville vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $207 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pylesville rentals

At Expedia, we put the best Pylesville vacation 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 Pylesville 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 Pylesville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pylesville. 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

Can I find a vacation rental in Pylesville?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Pylesville, or you can go with a secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Pylesville has to offer?

River Rock Room at Muse House: Secluded Luxury in horse country. : This vacation home rental outside of Pylesville is located in a rural location and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What can I see and do in Pylesville?

Explore the area and family-friendly sights such as Guppy Gulch Quarry, or get out into nature at a spot like Ladew Topiary Gardens. Rocks State Park and Holtwood Dam are a couple of places you'll find in the larger area.

What are vacation rentals like in Pylesville?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Pylesville. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family trips.