Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

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

10.0 out of 10, Exceptional, (22)
"Very nice cottage, as advertised"
The price is AU$322
includes taxes & fees
5 Oct - 6 Oct
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Waters Edge

10.0 out of 10, Exceptional, (137)
"Our stay was cut short but Brian and his wife were amazing host. We will definitely be returning "
Waters Edge

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

9.8 out of 10, Exceptional, (248)
"Beautiful, well cared for rental with a spectacular view."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

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

2.0 star property
10.0 out of 10, Exceptional, (21)
"We come to Lancaster 1 to 2 times a year and I must say this was one of the best trips we’ve taken. The house was incredibly clean and cozy. Bryan and Jenn out did themselves with the decor and wonderful hospitality! Waking up to the horses and view each morning made the trip even more special. We are already planning our trip for next year!! "
A working horse farm in Southern Lanc Co., nestled in Amish country.

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

9.6 out of 10, Exceptional, (9)
"It was a quiet calm retreat for us to stay during our family time "
The price is AU$531
includes taxes & fees
8 Oct - 9 Oct
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (100)
"Everything about this rental was easy, from check in to departure. We had one challenge with the TV and the host answered my text immediately and solved the issue for us. House was clean and as described in the listing. Highly recommend. "
Waterfront house with amazing views. Top of the Chesapeake

Restful Non-Shared Basement Suite In Harford MD

The price is AU$172
includes taxes & fees
12 Oct - 13 Oct
Restful Non-Shared Basement Suite In Harford MD

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

9.8 out of 10, Exceptional, (280)
"Absolutely love the views of the water, we had breakfast and lunch outside whenever the weather permits, and thoroughly enjoyed the peacefulness of the surroundings. Host Brian was very responsive and followed up quickly on a few of my requestsAll in all, enjoyed the stay"
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

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

10.0 out of 10, Exceptional, (255)
"This house is beautiful! Such an awesome set-up and the ideal spot for individuals that like the outdoors. Very spacious, homey vibe! The wrap around porch was so nice to hangout on!"
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (33)
"Our group had a great time on the Docside Doghouse. The communication with property owners was excellent and the property was exactly as advertised. Location is ideal"
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (276)
"We had such a great weekend at this property. It was beautiful and such a relaxing location. House had everything we needed. We hope to be back!! "
Captivating Chesapeake experience

Chic Towson Retreat: 4BR Getaway Near Baltimore

Chic Towson Retreat: 4BR Getaway Near Baltimore

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (144)
"Nice property with amazing views. Celebrated college graduation with family. Young ones had fun looking at ducks. Plenty of room for a large group."
The price is AU$931
includes taxes & fees
8 Oct - 9 Oct
5-bedroom vacation home 5 minutes from historic Charlestown

Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

9.8 out of 10, Exceptional, (6)
"This property was amazing! My family of six, really enjoyed the pool, large yard, for one including a balcony, toys for the kids, and many more! Will definitely be staying again in the future"
The price is AU$2,068
includes taxes & fees
1 Oct - 2 Oct
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

Charming cottage overlooking pond and meadows

10.0 out of 10, Exceptional, (69)
"We loved it here and would happily come back, it was cosy but also more than enough space for our family of five."
Charming cottage overlooking pond and meadows

8-Bedroom Luxury Home in Baltimore County

10.0 out of 10, Exceptional, (15)
"Great home, great location and would recommend to anyone looking to stay in the area with a large family or friends "
8-Bedroom Luxury Home in Baltimore County

* Lovely Gem w/ Perfect Combo of Flair & Class *

10.0 out of 10, Exceptional, (58)
"This little duplex is perfect for a couple of people and those traveling with a pet. The improvements made to the backyard, the parking spot, and the interior were all noticeable investments in comfort for guests. I look forward to my next trip to the area. Would definitely stay again"
The price is AU$414
includes taxes & fees
9 Oct - 10 Oct
* Lovely Gem w/ Perfect Combo of Flair & Class *

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

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

9.0 out of 10, Wonderful, (4)
"Loved the rivershack! Great place with many extras. It doesn't get any better than paddling on the Susquehanna River!"
The price is AU$658
includes taxes & fees
1 Oct - 2 Oct
The River Shack *kayaks*hottub*fishing*quiet*family

EV Charger Ready Townson Town Center Gem 3B2.5B

8.4 out of 10, Very good, (6)
EV Charger Ready Townson Town Center Gem 3B2.5B
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

Find out more about Chestnut Hill

Everything you need to know about Chestnut Hill holiday rentals

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

Chestnut Hill holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestnut Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestnut Hill holiday rentals we have selected for you start as low as AU$172 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chestnut Hill rentals

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

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. 

Frequently asked questions

Are there holiday rentals in Chestnut Hill?

Yes, there are holiday rentals close to the most popular sights in Chestnut Hill, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chestnut Hill has to offer?

Waters Edge: This holiday home rental outside of Chestnut Hill is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Rocks State Park and Harford Community College are a couple of places you'll find in the wider area.

What are holiday rentals like in Chestnut Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.