Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

9.6 out of 10, Exceptional, (59)
"Lovely location"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

10.0 out of 10, Exceptional, (239)
"House was clean and a very nice location. "
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, (12)
"Beautiful place , peaceful, just a breathe of fresh air . They were great and responsive "
A working horse farm in Southern Lanc Co., nestled in Amish country.

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

10.0 out of 10, Exceptional, (251)
"The pictures does no justice to this listing. It was absolutely beautiful and the stay was awesome. The hostbwas kind and generous. We had everything that we needed. Definitely would book again if I am going to be in the area. "
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

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

9.6 out of 10, Exceptional, (5)
"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 NZ$2,257
includes taxes & fees
13 Aug - 14 Aug
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

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

9.4 out of 10, Exceptional, (34)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Charming cottage overlooking pond and meadows

10.0 out of 10, Exceptional, (65)
"A quiet beautiful home in the heart of Amish country. Our whole family loved this place. "
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, (30)
"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.

The Chalet is located in the woods of a gated property with a covered porch.

9.4 out of 10, Exceptional, (22)
"Beautiful little house, great surroundings. We live every minute."
The Chalet is located in the woods of a gated property with a covered porch.

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (179)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

Waters Edge

10.0 out of 10, Exceptional, (131)
"Stunning views await you from every room, the minute you open the door! Such a picturesque setting. Our host was a pleasure to deal with. The home is immaculate and has every creature comfort you could want. We hope to stay again at Water's Edge."
Waters Edge

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (99)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake

Sailor's Sunrise Cottage - Chesapeake Bay

9.4 out of 10, Exceptional, (49)
"Landscaping was a little lacking. We're older so the low furnishings were a little challenging, but overall; very relaxing and pretty much what we expected. "
Sailor's Sunrise Cottage - Chesapeake Bay

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (142)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is NZ$1,060
includes taxes & fees
13 Aug - 14 Aug
5-bedroom vacation home 5 minutes from historic Charlestown

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (270)
"Beautiful home and setting!"
Captivating Chesapeake experience

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

9.0 out of 10, Wonderful, (2)
"Loved the rivershack! Great place with many extras. It doesn't get any better than paddling on the Susquehanna River!"
The price is NZ$760
includes taxes & fees
2 Sept - 3 Sept
The River Shack *kayaks*hottub*fishing*quiet*family

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

10.0 out of 10, Exceptional, (18)
"Was a charming place to stay close to everything"
The price is NZ$351
includes taxes & fees
13 Aug - 14 Aug
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Secluded Scenic Retreat, Amish Country, Vineyards

10.0 out of 10, Exceptional, (2)
"Nice house, very peaceful "
Secluded Scenic Retreat, Amish Country, Vineyards

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (100)
"This was our 2nd time staying at the property and everything was just perfect! The house is fully stocked, owners are very responsive, the home is very clean, and the beds are super comfy!"
The price is NZ$460
includes taxes & fees
18 Aug - 19 Aug
* Stunning New Bungalow Perfect for Everyone *

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

9.6 out of 10, Exceptional, (8)
"It was a quiet calm retreat for us to stay during our family time "
The price is NZ$575
includes taxes & fees
14 Aug - 15 Aug
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.
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

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?

Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!: This holiday home rental outside of Chestnut Hill is located on a river, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.