Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

* Beautiful Oasis w/ No Detail Spared *
9.8 out of 10, Exceptional, (32)
"We were very comfortable staying here while our hardwoods floors were being refinished."
The price is NZ$308
per night
23 Jun - 24 Jun
* Beautiful Oasis w/ No Detail Spared *
Waters Edge
10.0 out of 10, Exceptional, (92)
"Really nice property."
Waters Edge
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
10.0 out of 10, Exceptional, (197)
"This property was wonderful. It was just as advertised. The home is very inviting including anything you need to cook with. The beds were comfortable. The cleaning crew did a wonderful job. We felt completely comfortable there. We’d rent again without hesitation."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
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Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
9.6 out of 10, Exceptional, (36)
"This location was perfect for the many colleges in the area. I was visiting my college athlete at Morgan State. The house is very cozy and had everything we needed. I was able to cook a few nice meals while I was there. Our Host was very attentive and responded very quickly to the few questions I had. We will definitely look to reserve this property again."
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
Gorgeous Eight Bedroom Luxury Estate Home in Baltimore County
10.0 out of 10, Exceptional, (6)
"The house is actually the same as the pictures. Beautiful property, spacious downstairs and basement and so many bedrooms! We stayed with a college team and every single player had space and their own bed to sleep in. If we ever make it back to USA lacrosse headquarters, we will definitely book again!"
Gorgeous Eight Bedroom Luxury Estate Home in Baltimore County
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
9.8 out of 10, Exceptional, (240)
"Getting to the property is a very scenic drive through the country and only gets better when you check in. The house is absolutely gorgeous with a breathtaking view. We watched eagles flying around every morning while eating breakfast on the porch. The view of the lake is unmatched anywhere. The house was very clean and well stocked with everything we needed. The lake was very peaceful with just a handful of boats and jetskis. We thoroughly enjoyed our time here and will be booking again."
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (20)
"The kids joined us for a weekend on our sailboat, this was the perfect spot to get together after a long day on the water. My one son set a new record on the PAC Man and the other caught a beautiful bass off the dock. The river view from the sunroom is spectacular! Everyone always migrated there. Great time had by all. We will be back in the fall."
Waterfront Oasis w/ Private Dock, 3BR/2BA
* Private Suite Full of Style & Comfort *
9.2 out of 10, Wonderful, (28)
"This place is just as advertised! Comfortable and well appointed. I enjoyed that there were all the appliances and utensils we needed, including a measuring cup! We also really appreciated the coffee and tea set up, including creamer, sugar and Splenda. It's so nice to be able to make coffee in the morning. The bed was very comfortable and even though it is a basement apartment, there are still a couple of windows, so it doesn't really feel subterranean. Good water pressure, and the linens...
The price is NZ$280
per night
16 Jun - 17 Jun
* Private Suite Full of Style & Comfort *
PERUSE OUR INCREDIBLE REVIEWS! Creekside Cottage Awaits Your Visit!
10.0 out of 10, Exceptional, (221)
"I would go back tomorrow if i could. No one could be a better hostess than Carol. Thank you so much"
PERUSE OUR INCREDIBLE REVIEWS! Creekside Cottage Awaits Your Visit!
Charming cottage overlooking pond and meadows
10.0 out of 10, Exceptional, (33)
"very peaceful and relaxing! Our kids loved playing in the pond and seeing the farm animals next door."
Charming cottage overlooking pond and meadows
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (11)
"This was my second time to the houseboat and it was wonderful! It is conveniently located and many small shops, restaurants, brewery/bars are walking distance, and a short drive to wineries. Also a park right across from the marina."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
River Haven with Hot Tub | 4 Bed, 3.5 Bath
9.8 out of 10, Exceptional, (17)
"The house was great and had a ton to do! Which was awesome for us because it rained while we were there. The foosball, ping pong and air hockey tables provided a ton of entertainment."
River Haven with Hot Tub | 4 Bed, 3.5 Bath
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
The price is NZ$531
per night
6 Jun - 7 Jun
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
* Stunning New Bungalow Perfect for Everyone *
9.8 out of 10, Exceptional, (81)
"Stayed here the weekend of our nephew's wedding. Great location. Convenient for Towson and northern Baltimore."
The price is NZ$448
per night
12 Jun - 13 Jun
* Stunning New Bungalow Perfect for Everyone *
Spacious Pequea Retreat w/ Dock & Hot Tub!
9.4 out of 10, Exceptional, (19)
"Space is great. Dock needed to be cleaned. Junk on ground in that area. The feral cats are a nuisance. All that being said, the furnishings are fine- kitchen is well stocked- and you can’t beat the outside space. The surrounding area is run down."
Spacious Pequea Retreat w/ Dock & Hot Tub!
Cozy and comfortable four bedroom home with all you need for a great stay
2.0 out of 10, (1)
"Dirty, inconvenience for people, appliances not working… furniture broke, late responses from owner"
Cozy and comfortable four bedroom home with all you need for a great stay
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (89)
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (34)
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
New Townhouse - 2 Car Garage by CCBC & Franklin Sq
10.0 out of 10, Exceptional, (18)
"Very nice place, great location, safe neighborhood, great communication with host. Would recommended!"
New Townhouse - 2 Car Garage by CCBC & Franklin Sq
Cozy Farm Apartment (A) surrounded by wooded private park
10.0 out of 10, Exceptional, (24)
"There were four adults who shared apartment A. It was a great place to just "hang out." We enjoyed sitting around the fire ring listening to the birds and walking over to see the horses and deer in the field. We only stayed two nights. The beds were comfortable and the showers had great water pressure. The kitchen was equipped with most of what you would need, although we could have used a grater for cheese and a baking dish. Overall, we had a very enjoyable time and would stay here again."
Cozy Farm Apartment (A) surrounded by wooded private park
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See all available properties in Chestnut 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.

Other types of properties in Chestnut Hill you may be interested in

Embassy Suites by Hilton Baltimore Hunt Valley
3.5 star property
8.2 out of 10, Very good, (1009)
"Fantastic venue with on site services including indoor pool and gym. Very friendly staff! "
The price is NZ$256
per night
24 Jun - 25 Jun
Embassy Suites by Hilton Baltimore Hunt Valley
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
7.4 out of 10, Good, (1008)
"The Quality Inn & Suites Bel Air in Edgewood, MD was the ideal spot to stay while preparing for a major writing assignment that required absolute uninterrupted attention. It was quiet, clean, affordable and quite spacious. In addition, it was accessible to several eateries as well as shopping spots. The front desk personnel was very helpful and professional."
The price is NZ$113
per night
16 Jun - 17 Jun
Quality Inn & Suites Bel Air I-95 Exit 77A
Holiday Inn Express Towson - Baltimore North, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1008)
"comfortable and clean?"
The price is NZ$189
per night
23 Jun - 24 Jun
Holiday Inn Express Towson - Baltimore North, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chestnut Hill holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chestnut Hill. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chestnut Hill. Seeing all the best attractions is bound to make you fall in love with Chestnut Hill. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chestnut Hill short-term rentals, that won’t be hard to do.

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?

LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK : This holiday home rental outside of Chestnut Hill is located on a lake, and has a balcony, a garden and a BBQ 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 holiday with amenities such as 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 Susquehanna State Park. Harford Community College and Liriodendron Mansion 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.

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