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Chestnut Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chestnut Hill vacation rentals

Living area

1. 2 Bd/1ba Apt for the price 1 Room at the Hilton

2 Bd/1ba Apt for the price 1 Room at the Hilton
Bel Air
$240 nightly
The price is $254
Nov 22 - Nov 23
Total with taxes and fees
2 Bd/1ba Apt for the price 1 Room at the Hilton
A house with a curved roof, a garden with various plants and flowers, and a red garage.

2. Cozy 1-bedroom bungalow in quaint Darlington with AC

Cozy 1-bedroom bungalow in quaint Darlington with AC
Darlington
10.0 out of 10, Exceptional, (12 reviews)
"Excellent host, property, and experience. We enjoyed our stay, and we will be back."
United States
Kevin A.
$129 nightly
The price is $137
Nov 10 - Nov 11
Total with taxes and fees
Cozy 1-bedroom bungalow in quaint Darlington with AC
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

3. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
$81 nightly
The price is $86
Nov 16 - Nov 17
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

4. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
$134 nightly
The price is $142
Nov 11 - Nov 12
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A single-story white house with a front porch, a mailbox, and a number '715' on the door.

5. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
United States
Claudia L.
$288 nightly
The price is $289
Nov 10 - Nov 11
Total with taxes and fees
Watch Deer from a Farm Cottage
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

6. 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
9.8 out of 10, Exceptional, (60 reviews)
"Unique charming place to relax."
United States
Nimia N.
$205 nightly
The price is $217
Nov 10 - Nov 11
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A kitchen with white cabinets, a wooden countertop, a built-in oven, and a window.

7. 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, (18 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$202 nightly
The price is $214
Nov 28 - Nov 29
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior

8. Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
Port Deposit
10.0 out of 10, Exceptional, (3 reviews)
"Renee & Pat were excellent hosts and we will definitely try to book again when in the area. Everything was as advertised and much more. Being pet friendly was a plus. We enjoyed two restaurants in the area while there, Lee's Landing and Old South Smokehouse, highly recommend!"
United States
Don S.
$194 nightly
The price is $194
Nov 10 - Nov 11
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
A wooden cabin with a circular entrance, a fire pit, and a stone pathway leading to it.

9. Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy

Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
Delta
10.0 out of 10, Exceptional, (5 reviews)
"We had a perfect weekend at this little cabin get-away! The listing pictures portrayed the site perfectly. Well before check-in, the D-Lux team was in touch to make sure we had check-in codes and to answer any questions if we would have had them. Upon arrival the place was spotless and very inviting. It was adequately stocked with necessities and even had a few extra touches that we appreciated. The hammock, hottub, and sauna were clean and perfect and helped us have a truly relaxing weekend....
United States
Megan K.
$358 nightly
The price is $396
Nov 16 - Nov 17
Total with taxes and fees
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

10. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (33 reviews)
"The Port Deposit area is a favorite "mini-vacation" location with great bars/restaurants and beautiful walks. We've stayed at this property a number of times and we've found the rooms to be perfect for our needs. "
United States
Lance W.
$288 nightly
The price is $305
Nov 10 - Nov 11
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
A two-story wooden cabin with a balcony, surrounded by a well-maintained garden and trees.

11. The River Shack *kayaks*hottub*fishing*quiet*family

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.8 out of 10, Exceptional, (14 reviews)
"This property was great, everything you could need was provided. We really enjoyed our stay"
United States
Barb R.
$373 nightly
The price is $413
Nov 11 - Nov 12
Total with taxes and fees
The River Shack *kayaks*hottub*fishing*quiet*family
A wooden deck with a stone wall, a covered grill, and a view of a lake.

12. Waterfront Retreat w/ Hot Tub, Games & Views

Waterfront Retreat w/ Hot Tub, Games & Views
Whiteford
9.8 out of 10, Exceptional, (30 reviews)
"We like the property, it's location, and views.."
United States
Nazia M.
$1,370 nightly
The price is $1,530
Nov 10 - Nov 11
Total with taxes and fees
Waterfront Retreat w/ Hot Tub, Games & Views
A dining room with a large table, wooden chairs, a chandelier, and large windows with blinds.

13. The Manor Cottage at Harford Hill

The Manor Cottage at Harford Hill
Fallston
$3,957 nightly
The price is $4,194
Nov 10 - Nov 11
Total with taxes and fees
The Manor Cottage at Harford Hill
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 Chestnut Hill Hotel Reviews

WoodSpring Suites Baltimore White Marsh - Nottingham

WoodSpring Suites Baltimore White Marsh - Nottingham

10/10 Excellent
"I had a one night day. And the staff was very helpful. My room was clean and I like the overall area that had shops nearby easy access, and easy to find."
Yvonne 1-night trip
Posted 1 hour ago
WoodSpring Suites Baltimore White Marsh - Nottingham

Find out more about Chestnut Hill

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

Chestnut Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestnut Hill. 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 Chestnut Hill 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 $142 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 Chestnut Hill rentals

At Expedia, we put the best Chestnut Hill 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 Chestnut Hill 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 Chestnut Hill 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 Chestnut Hill. 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 Chestnut Hill?

Yes, you can find vacation rentals close to the most popular sights in Chestnut Hill, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Chestnut Hill?

Waters Edge: This vacation home rental outside of Chestnut Hill is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What can I see and do in Chestnut Hill?

While exploring the area, visit family-friendly sights like Guppy Gulch Quarry, or get outside and enjoy nature at Ladew Topiary Gardens. Harford Community College and Liriodendron Mansion are a couple of places you'll find in the larger area.

What are vacation rentals like in Chestnut Hill?

Vacation rentals are private accommodations you can book for a couple days or more in Chestnut Hill. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip.