Chestnut Hill Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Chestnut Hill

Waters Edge

Pequea
10.0 out of 10, Exceptional, (140)
"For the third year in a row we enjoyed our family time in this beautiful and spacious home. The pool and hot tub are always a big hit. We rented a kayak one day which was fun. Due to some downpours of rain before and during our stay, the ground was a bit soggier than previous years where our grandkids liked to explore along the river. "
United States
Joyce M.
Waters Edge

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

Pequea
9.8 out of 10, Exceptional, (284)
"We loved the spacious rooms. We used the hot tub every night. The view from this property is so serene and relaxing. 100% recommend!"
United States
Carrie D.
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.0 out of 10, Very good, (5)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is NZ$1,477
includes taxes & fees
30 Nov - 1 Dec
Luxury Waterfront Home Built for Entertaining!

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

Port Deposit
10.0 out of 10, Exceptional, (30)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
The price is NZ$369
includes taxes & fees
6 Dec - 7 Dec
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

2.0 star property
Holtwood
10.0 out of 10, Exceptional, (26)
"Whole place was top notch! "
United States
Kelly P.
A working horse farm in Southern Lanc Co., nestled in Amish country.

Waterfront Oasis w/ Private Dock, 3BR/2BA

Middle River
9.4 out of 10, Exceptional, (39)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
United States
Vince E.
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

Havre de Grace
9.8 out of 10, Exceptional, (6)
"Beautiful home and property. The house was clean and welcoming and the pool was an absolute delight. Would definitely stay again! "
United States
Julia B.
The price is NZ$2,390
includes taxes & fees
28 Nov - 29 Nov
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

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

Drumore
10.0 out of 10, Exceptional, (261)
"Excellent property set out in the country. Second time we have stayed at this cottage and was amazing both times."
United States
Eric K.
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

Close to Hospital & White Marsh! Rosedale Townhome

2.0 star property
Nottingham
The price is NZ$942
includes taxes & fees
30 Nov - 1 Dec
Close to Hospital & White Marsh! Rosedale Townhome

Quarry Landing - Center of Town & River View - 3 Bedroom

Port Deposit
10.0 out of 10, Exceptional, (11)
"Very clean, spacious, comfortable house. Would stay there again. Great communication with the hosts."
United States
Courtney W.
The price is NZ$374
includes taxes & fees
1 Dec - 2 Dec
Quarry Landing - Center of Town & River View - 3 Bedroom

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

Airville
10.0 out of 10, Exceptional, (5)
"Great place to stay, very clean and freshly updated house. "
United States
Brad W.
The price is NZ$781
includes taxes & fees
9 Dec - 10 Dec
Waterview. Hot Tub. Gas Firepit. Lancaster 40 min.

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

Fawn Grove
9.6 out of 10, Exceptional, (12)
"Two night stay was very nice. Great living, kitchen and bedroom spaces. Very quiet area."
United States
Rene S.
The price is NZ$609
includes taxes & fees
9 Dec - 10 Dec
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

8-Bedroom Luxury Home in Baltimore County

Phoenix
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 "
United States
Michael F.
8-Bedroom Luxury Home in Baltimore County

Nature's Grove Cabin

Delta
10.0 out of 10, Exceptional, (5)
"Nice place. Peaceful. "
United States
Sherry S.
Nature's Grove Cabin

Restful Non-Shared Basement Suite In Harford MD

Bel Air
10.0 out of 10, Exceptional, (2)
"Check in was quick and easy, property was exactly as I thought it would be and amenities were great."
United States
Joseph N.
The price is NZ$198
includes taxes & fees
2 Dec - 3 Dec
Restful Non-Shared Basement Suite In Harford MD

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

Pequea
10.0 out of 10, Exceptional, (251)
"loved the view and bald eagles"
United States
Jim E. S.
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

Modern 3-bedroom cottage in Drumore, southern Lancaster County

Drumore
9.8 out of 10, Exceptional, (10)
"Great place - very clean and cozy. Beautiful farm next door, loved seeing the cows come right up to the property line. Appreciated the large dining table with comfy chairs and comfy beds"
United States
Anonymous traveller
Modern 3-bedroom cottage in Drumore, southern Lancaster County

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

White Marsh
10.0 out of 10, Exceptional, (16)
"Beautiful views and equipped with everything you could ever want! They were even kind of enough to build us a fire for smores. "
United States
Nusayba H.
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

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

Havre de Grace
9.6 out of 10, Exceptional, (34)
"This was our second stay and it was just as relaxing and peaceful as the first time. Highly recommend!"
United States
Kimberly D.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

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

Airville
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!"
United States
Rob H.
The River Shack *kayaks*hottub*fishing*quiet*family
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.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Chestnut Hill Hotel Reviews

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 favorite 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 depends 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 NZ$198 per night. Entering your travel dates in the search wizard you might find 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. 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.