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Chestnut Hill Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chestnut Hill vacation rentals

A covered patio area with stone flooring, wooden beams, and a fire pit.

1. Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
9.8 out of 10, Exceptional, (6 reviews)
"I had such a great stay! Perfect spot for an individual or couple. Clean, quiet, and private. Would definitely recommend!"
United States
Tyler P.
$109 nightly
The price is $116
Sep 16 - Sep 17
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

2. 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, (52 reviews)
"Very unique property, with lots of history. We enjoyed our short stay."
United States
Terry R S.
$199 nightly
The price is $210
Sep 9 - Sep 10
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A bedroom with a sliding glass door, a bed with white bedding, and a nightstand.

3. Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
Airville
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful peaceful spot."
United States
Emily L.
$515 nightly
The price is $569
Sep 8 - Sep 9
Total with taxes and fees
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

4. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (6 reviews)
"Pet friendly."
United States
Claudia L.
$383 nightly
The price is $386
Oct 1 - Oct 2
Total with taxes and fees
Watch Deer from a Farm Cottage
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table with chairs.

5. Working horse farm retreat! Convenient to wedding venue!

Working horse farm retreat! Convenient to wedding venue!
White Hall
9.8 out of 10, Exceptional, (56 reviews)
"The place was amazing and had everything we needed. "
United States
Kate and Ray T.
$291 nightly
The price is $336
Sep 15 - Sep 16
Total with taxes and fees
Working horse farm retreat! Convenient to wedding venue!
A wooden cabin with a circular entrance, a fire pit, and a stone pathway leading to it.

6. 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, (3 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.
$403 nightly
The price is $445
Sep 21 - Sep 22
Total with taxes and fees
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy

7. 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, (2 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.
$186 nightly
The price is $187
Sep 8 - Sep 9
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland
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.

8. 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
$106 nightly
The price is $112
Sep 13 - Sep 14
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC
A room with a wooden floor, a ceiling fan, a refrigerator, a chair, a lamp, and a window with curtains.

9. 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.
$271 nightly
The price is $287
Sep 10 - Sep 11
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette
A kitchen with white cabinets, a wooden countertop, a sink, a stove, and shelves with dishes.

10. 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, (15 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$272 nightly
The price is $289
Sep 9 - Sep 10
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
A wooden cabin with a fire pit in the center, surrounded by Adirondack chairs.

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

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.6 out of 10, Exceptional, (10 reviews)
"This property was great, everything you could need was provided. We really enjoyed our stay"
United States
Barb R.
$416 nightly
The price is $459
Sep 15 - Sep 16
Total with taxes and fees
The River Shack *kayaks*hottub*fishing*quiet*family
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
9.8 out of 10, Exceptional, (7 reviews)
$175 nightly
The price is $186
Sep 9 - Sep 10
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A blue door with a wreath and a welcome mat.

13. Authentic working horse farm stay! Quiet, rural, and close to nature!

Authentic working horse farm stay! Quiet, rural, and close to nature!
White Hall
9.8 out of 10, Exceptional, (39 reviews)
"Clean, quiet location perfect for a relaxing get away."
United States
Scott J.
$310 nightly
The price is $358
Sep 7 - Sep 8
Total with taxes and fees
Authentic working horse farm stay! Quiet, rural, and close to nature!
A modern living room with a blue sofa set, a wooden coffee table, and a patterned rug.

14. Home away from home with WiFi and AC in delightful Parkville

Home away from home with WiFi and AC in delightful Parkville
Carney
$192 nightly
The price is $222
Sep 7 - Sep 8
Total with taxes and fees
Home away from home with WiFi and AC in delightful Parkville
A dining room with a large table, wooden chairs, a chandelier, and large windows with blinds.

15. The Manor Cottage at Harford Hill

The Manor Cottage at Harford Hill
Fallston
$3,568 nightly
The price is $3,782
Sep 7 - Sep 8
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"Front desk pleasant and helpful, but… no accessible rooms available. Also, only non pet room available (even though reservations were made) was on 2nd floor and elevator out of service. Room itself was clean. Breakfast was good."
Robert 1-night trip
Posted 8 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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 $186 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?

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK : This vacation home rental outside of Chestnut Hill is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.