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Chestnut Hill Vacation Rentals

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Our top choices for Chestnut Hill vacation rentals

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, (3 reviews)
"very clean and cozy host was very nice . They had everything we needed for our stay. Very convenient to all local activities. Would stay there agin when in area."
United States
Jacquelyn O.
$146 nightly
The price is $155
Jul 7 - Jul 8
Total with taxes and fees
Cozy 1-bedroom bungalow in quaint Darlington with AC

Restful Non-Shared Basement Suite In Harford MD

Restful Non-Shared Basement Suite In Harford MD
Bel Air
10.0 out of 10, Exceptional, (3 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.
$100 nightly
The price is $105
Jun 29 - Jun 30
Total with taxes and fees
Restful Non-Shared Basement Suite In Harford MD

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
$85 nightly
The price is $90
Jun 29 - Jun 30
Total with taxes and fees
Charming 2-bedroom house in Aberdeen with WiFi and AC

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

Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy
Delta
$311 nightly
The price is $343
Jun 30 - Jul 1
Total with taxes and fees
Creekside Cabin: Sauna | Hot Tub | Fire Pit | Romantic | Peaceful | Cozy

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, (45 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
$200 nightly
The price is $211
Jun 30 - Jul 1
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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, (1 review)
"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.
$187 nightly
The price is $188
Jun 29 - Jun 30
Total with taxes and fees
Luxury Bed and Breakfast for a Weekend Getaway near Susquehanna State Park, Maryland

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
$161 nightly
The price is $170
Jul 6 - Jul 7
Total with taxes and fees
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
$271 nightly
The price is $287
Jun 28 - Jun 29
Total with taxes and fees
Private 3 room Queen Suite w/Kitchenette

Working horse farm retreat! Convenient to wedding venue!

Working horse farm retreat! Convenient to wedding venue!
White Hall
9.8 out of 10, Exceptional, (54 reviews)
"The place was amazing and had everything we needed. "
United States
Kate and Ray T.
$253 nightly
The price is $292
Jun 28 - Jun 29
Total with taxes and fees
Working horse farm retreat! Convenient to wedding venue!

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Havre de Grace
10.0 out of 10, Exceptional, (11 reviews)
"The house was very cozy and close to my venue Jennifer was very responsive with any questions nice place to stay roomy"
United States
Liza
$244 nightly
The price is $258
Jul 7 - Jul 8
Total with taxes and fees
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

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, (1 review)
"Booked this property as a last minute, overnight getaway for myself and it was fantastic! The apartment, grounds and hot tub was squeaky clean. Kitchen was clean and stocked with utensils and even had a coffee bar, different tea packets and a snack basket. Bathroom was fully stocked with towels, basic toiletries and everything I needed. Bed was comfortable and closets had extra blankets if needed. Inside and outside patio furniture was comfy. I loved watching the sunset from the hot tub! Also...
United States
Kayla K.
$182 nightly
The price is $193
Jul 6 - Jul 7
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

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

The River Shack *kayaks*hottub*fishing*quiet*family
Airville
9.6 out of 10, Exceptional, (7 reviews)
"We had a very quiet and peaceful stay. Would most definitely stay again!"
United States
Nathan D.
$455 nightly
The price is $502
Jun 30 - Jul 1
Total with taxes and fees
The River Shack *kayaks*hottub*fishing*quiet*family

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, (14 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
$284 nightly
The price is $301
Jun 30 - Jul 1
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom

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

Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.
Airville
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home!"
United States
Alison C.
$628 nightly
The price is $693
Jun 29 - Jun 30
Total with taxes and fees
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

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)
"Great location"
United States
Bruce S.
$253 nightly
The price is $292
Jun 28 - Jun 29
Total with taxes and fees
Authentic working horse farm stay! Quiet, rural, and close to nature!
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

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 $90 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.