Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

Waters Edge
10.0 out of 10, Exceptional, (111)
"Beautiful home. We all had plenty of room, 12 total. Very clean. Accurate to pictures on site. Very easy check in, and Brian was very helpful showing us the house. We all loved our stay. The sunrise and sunsets were gorgeous over the lake view. "
Waters Edge
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
10.0 out of 10, Exceptional, (218)
"The lake house was perfect for two couples here for a wedding. Brian was fabulous. We loved the view and the trains. Thank you so much. "
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Charming cottage overlooking pond and meadows
10.0 out of 10, Exceptional, (50)
"The house was clean and cozy. The coffee cake that was left for us to enjoy was delicious. Would definitely recommend this place."
Charming cottage overlooking pond and meadows
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
10.0 out of 10, Exceptional, (236)
"Creekside Cottage was exactly as described. The property was clean, comfortable and the perfect location for our annual golf getaway. We really enjoyed our stay."
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Waterfront Oasis w/ Private Dock, 3BR/2BA
9.8 out of 10, Exceptional, (26)
"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...
Waterfront Oasis w/ Private Dock, 3BR/2BA
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (94)
"Cute, up-to-date house, peaceful location, beautiful views. Well supplied kitchen, including sharp knives! Excellent communication with owner – prompt and helpful. Fast internet. Could use more bathroom surface areas; a few more hooks to hang clothes and towels; and an additional umbrella or two outside for shade. My mom, sister, and I thoroughly enjoyed our stay."
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, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
River Haven with Hot Tub | 4 Bed, 3.5 Bath
9.8 out of 10, Exceptional, (22)
"Very secluded and a great house for a family reunion."
River Haven with Hot Tub | 4 Bed, 3.5 Bath
Pet-Friendly Delta Cabin w/ Private Hot Tub!
10.0 out of 10, Exceptional, (22)
"My husband and I wanted a private location we could relax at and were not disappointed. The cabin was very clean, nicely furnished, and was everything we were looking for. The coffee bar was a very nice addition. The hot tub was clean and extremely relaxing as well. We had never played pickle ball but how can you say no to a private court! We would definitely stay again and would highly recommend!!"
Pet-Friendly Delta Cabin w/ Private Hot Tub!
Beautiful Colonial Style Home in Nottingham PA
9.8 out of 10, Exceptional, (6)
"Loved the preserved historic quality of the property. So tastefully furnished and lovely. Nice and quiet neighborhood. The exposed beams certainly let you know when someone was in the room over your head but so worth it for the character."
Beautiful Colonial Style Home in Nottingham PA
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (18)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
9.8 out of 10, Exceptional, (260)
"Karen and Brian really, really care about their guests. They are very courteous, prompt and accommodating. So far, we've stayed there 3 times, and we will be staying at The Lake House every year, guaranteed! God Bless Karen, Brian, and Pequea, PA!"
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (55)
"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Towson Elite Apartment
9.4 out of 10, Exceptional, (3)
"Staying at this property was great ! Everything was as pictured. My sister, neice and I really enjoyed. Convenient location."
The price is AU$278
includes taxes & fees
25 Nov - 26 Nov
Towson Elite Apartment
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
9.2 out of 10, Wonderful, (44)
"The stay was good. The guest bedroom mattress was not to comfortable and the pool was closed but everything was fine."
Lovely colonial-style home with pool access, firepit & large yard - dog-friendly
* Lovely Gem w/ Perfect Combo of Flair & Class *
10.0 out of 10, Exceptional, (47)
"This place suited our needs, clean and roomy!"
The price is AU$412
includes taxes & fees
26 Nov - 27 Nov
* Lovely Gem w/ Perfect Combo of Flair & Class *
8-bedroom vacation home 28 minutes from Johns Hopkins University
10.0 out of 10, Exceptional, (12)
"A group of us had a great long-weekend visit! The house is absolutely beautiful. We had a group of 10, and the house could have easily accommodated twice as many. The property was spotless and very well maintained. Highly recommended!"
8-bedroom vacation home 28 minutes from Johns Hopkins University
Spacious Pequea Retreat w/ Dock & Hot Tub!
9.4 out of 10, Exceptional, (23)
"We had a great time celebrating my wife's 60th birthday. Perfect setting to relax."
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"
The price is AU$844
includes taxes & fees
24 Nov - 25 Nov
Cozy and comfortable four bedroom home with all you need for a great stay
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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Other types of properties in Chestnut Hill you may be interested in

Holiday Inn Express Towson - Baltimore North, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (1005)
"Property was very clean and staff very friendly. It’s close to where I was visiting and near major roads. Very convenient. "
The price is AU$191
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express Towson - Baltimore North, an IHG Hotel
Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
7.2 out of 10, Good, (1001)
"The breakfast was very basic, no meat, eggs juice or danish etc."
The price is AU$87
includes taxes & fees
1 Dec - 2 Dec
Quality Inn & Suites Bel Air I-95 Exit 77A
Embassy Suites by Hilton Baltimore Hunt Valley
3.5 star property
8.2 out of 10, Very good, (1008)
" Clean and comfortable"
The price is AU$189
includes taxes & fees
22 Dec - 23 Dec
Embassy Suites by Hilton Baltimore Hunt Valley
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Maize Quest Fun Park, 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.