Pleasant Hills Vacation Rentals

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In two weeks
Dec 26 - Dec 28
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In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Pleasant Hills vacation rentals

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

Cottage in Port Deposit

Quarry Landing - Center of Town & River View - 3 Bedroom
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 6 - Jan 7, 2026
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
1 bedroom, WiFi, bed sheets, wheelchair access
Restful Non-Shared Basement Suite In Harford MD

Vacation Home in Bel Air

Restful Non-Shared Basement Suite In Harford MD
10.0 out of 10, Exceptional, (2)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
$105 nightly
The price is $111
Dec 18 - Dec 19
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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.
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Vacation Home in Bel Air

Small House on Gentleman’s Farm
10.0 out of 10, Exceptional, (13)
"Great little getaway, very clean, and the bedding was so comfy! "
United States
Joan F.
$297 nightly
The price is $299
Dec 17 - Dec 18
Total with taxes and fees
Small House on Gentleman’s Farm
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

5 Mi to Downtown Baltimore: Quiet Home w/ Porch
3.0 star property
9.0 out of 10, Wonderful, (2)
"It took a whole day for the house to get warm.No utensils.And last but not least the heat was turned off in the middle of the night.Monday morning was very cold,that’s why we left at nine thirty. "
United States
Cathy
$431 nightly
The price is $498
Dec 15 - Dec 16
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Fridge, microwave, oven, stovetop
* Private Suite Full of Style & Comfort *

Apartment in Lutherville-Timonium

* Private Suite Full of Style & Comfort *
9.2 out of 10, Wonderful, (42)
"Owners were receptive when needed. All went smoothly. "
United States
David M.
$150 nightly
The price is $173
Dec 22 - Dec 23
Total with taxes and fees
* Private Suite Full of Style & Comfort *
Private kitchen
Cool townhome with AC in vibrant Baltimore

Vacation Home in Darley Park

Cool townhome with AC in vibrant Baltimore
2.0 star property
8.0 out of 10, Very Good, (1)
"It's an older house in an older neighborhood, but it was very quiet. Lots of room. "
United States
Naola V.
Cool townhome with AC in vibrant Baltimore
Exterior
Private 3 room Queen Suite w/Kitchenette

Apartment in Port Deposit

Private 3 room Queen Suite w/Kitchenette
10.0 out of 10, Exceptional, (29)
"Perfect location for that town. "
United States
Hisham M.
$243 nightly
The price is $258
Dec 15 - Dec 16
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
Interior
Convention Center corporate apartments

Apartment in Downtown Baltimore

Convention Center corporate apartments
4.0 star property
$226 nightly
The price is $266
Dec 14 - Dec 15
Total with taxes and fees
Convention Center corporate apartments
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Dec 14 - Dec 15
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Dining
HUGE 2 Bedroom Apt FREE parking II Queen Bed

Apartment in Midtown

HUGE 2 Bedroom Apt FREE parking II Queen Bed
8.4 out of 10, Very Good, (5)
"We came to visit a family member who lives nearby in Bolton Hill and was performing in a concert. This was walking distance and just perfect. We also really appreciated that our furry family member was also welcome. The apartment is wonderfully spacious and comfortable, too. Christopher always responded promptly to our every need. Thank you!"
United States
Catherine Dominique P.
$195 nightly
The price is $225
Dec 15 - Dec 16
Total with taxes and fees
HUGE 2 Bedroom Apt FREE parking II Queen Bed
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Cottage in Betterton

Grandma’s Cottage will wrap around you like a warm hug
$395 nightly
The price is $419
Jan 1 - Jan 2, 2026
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Property grounds
Hobbit House one of a kind home

Vacation Home in Bel Air

Hobbit House one of a kind home
10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
$298 nightly
The price is $299
Jan 13 - Jan 14, 2026
Total with taxes and fees
Hobbit House one of a kind home
Fridge, microwave, oven, stovetop
Cozy Modern Micro Apt in the Heart of Fells Point!

Apartment in Fells Point

Cozy Modern Micro Apt in the Heart of Fells Point!
9.0 out of 10, Wonderful, (31)
"We had such a great stay at the property. Everything was clean and welcoming. It was the perfect little place/space for my wife my 3 yr old son and myself. The street parking in the area was also good. We were able to find a spot right around the corner. The location of the property in relation to a lot of the sites in Fells Point was perfect as well. Everything 5 stars we would definitely recommend and We would definitely book again! "
United States
Bryan S.
$215 nightly
The price is $248
Dec 14 - Dec 15
Total with taxes and fees
Cozy Modern Micro Apt in the Heart of Fells Point!
Exterior
Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit

Apartment in Parkview/Woodbrook

Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit
10.0 out of 10, Exceptional, (1)
"This was a veryyyy comfortable VRBO . This was my first stay in Baltimore, and this stay has me on my way back soon. This can definitely be a place someone stays long term. Ed (host) has every recommendation you can think of (top tier) and if there’s a problem he’s on it QUICKLY. He has maintenance on call. The place is very clean and modern. You can cook, wash clothes, Netflix all day. The living room was my favorite part lol. It’s like tucked away. In the living room you have a view of the sun...
United States
Ticara J.
$215 nightly
The price is $248
Dec 27 - Dec 28
Total with taxes and fees
Parkside Gem: Luxe & Roomy by Historic Druid Hill l WIFI l Entire Unit
Smart TV
Charming Urban Retreat: 4 Bedroom, 2 Bath Townhouse in Baltimore City, Maryland

Vacation Home in New Northwood

Charming Urban Retreat: 4 Bedroom, 2 Bath Townhouse in Baltimore City, Maryland
2.0 star property
9.8 out of 10, Exceptional, (10)
"Clean with comfortable beds, pleasant spaces to cook, eat, and relax."
United States
Susan L.
$448 nightly
The price is $517
Dec 14 - Dec 15
Total with taxes and fees
Charming Urban Retreat: 4 Bedroom, 2 Bath Townhouse in Baltimore City, Maryland
Fridge, microwave, oven, stovetop
Perfect 4 Holidays: Fed Hill★Family★ 3BR 2BA★2 Parkings★Full Kitch★Walkscore 92

Vacation Home in South Baltimore

Perfect 4 Holidays: Fed Hill★Family★ 3BR 2BA★2 Parkings★Full Kitch★Walkscore 92
2.0 star property
10.0 out of 10, Exceptional, (4)
"House was in great condition, clean, and host was easily accessible. "
United States
Christopher L.
$251 nightly
The price is $290
Dec 23 - Dec 24
Total with taxes and fees
Perfect 4 Holidays: Fed Hill★Family★ 3BR 2BA★2 Parkings★Full Kitch★Walkscore 92
Basic Apartment, Balcony, City View | Terrace/patio
1-BD Home near Stadiums Free Parking

Apartment in Pigtown

1-BD Home near Stadiums Free Parking
3.0 star property
8.0 out of 10, Very Good, (6)
"Very convenient downtown location, OK-safe area, walkable to restaurants and bars. Easy and unrestricted street parking spots nearby. Nicely decorated inside, air conditioning and hot water working well, comfy bed, TV with streaming services, tidy bedroom and clean bathroom. Overall very satisfied, especially with the affordable price. "
United States
Nathan
$121 nightly
The price is $142
Dec 14 - Dec 15
Total with taxes and fees
1-BD Home near Stadiums Free Parking
Dining
3-bedroom townhome in superb Baltimore with AC

Vacation Home in Shipley Hill

3-bedroom townhome in superb Baltimore with AC
2.0 star property
7.0 out of 10, Good, (2)
"The host was not attentive at all. I couldn’t access the unit for about 4 hours after my check in time because the lock box was hard to get into. The host wanted me to drive to some unknown neighborhood to pick up a spare key. The furniture had stains on it. The walls had holes in them. The back yard was a disaster. The ceilings had water damage to them. The heat didn’t work and we didn’t have access to the WiFi so we couldn’t watch tv. I reached out to the host several times about all my...
United States
Michelle S.
3-bedroom townhome in superb Baltimore with AC
1 bedroom, iron/ironing board, free WiFi, bed sheets
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Vacation Home in Aberdeen

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
$198 nightly
The price is $210
Dec 14 - Dec 15
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
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 Pleasant Hills Hotel Reviews

Residence Inn by Marriott Baltimore Inner Harbor

Residence Inn by Marriott Baltimore Inner Harbor

10/10 Excellent
"Just the best option! "
Victor 5-night trip
Posted 3 days ago
Residence Inn by Marriott Baltimore Inner Harbor

Find out more about Pleasant Hills

Everything you need to know about Pleasant Hills 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 Pleasant Hills 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 Pleasant Hills vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Hills vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Hills. 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 Pleasant Hills 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 $112 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 Pleasant Hills rentals

At Expedia, we put the best Pleasant Hills 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 Pleasant Hills 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 Pleasant Hills 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 Pleasant Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Pleasant Hills?

Yes, we offer vacation rentals close to top sights in Pleasant Hills, or you can go with a more secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Pleasant Hills has to offer?

Rooftop Deck Escape! Free Parking!: This vacation home rental near Pleasant Hills is located in the city center and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Pleasant Hills?

Explore the area and family-friendly sights such as Natural History Society of Maryland Museum, or get out into nature at a spot like Miami Beach. While here, Gunpowder Falls State Park and McCourtney's General Store Museum are other places worth a visit.

What are vacation rentals like in Pleasant Hills?

Vacation rentals are private properties where you can stay for a long or short time in Pleasant Hills. Vacation rentals offer extras like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips.