Chestnut Hill Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Chestnut Hill

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

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

Pequea
9.8 out of 10, Exceptional, (284)
"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"
United States
Vance N.
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
Fridge, microwave, oven, stovetop
Waters Edge

Waters Edge

Pequea
10.0 out of 10, Exceptional, (139)
"Our stay was cut short but Brian and his wife were amazing host. We will definitely be returning "
United States
Daniel and Cara R.
Waters Edge
Beach
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

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

Pequea
10.0 out of 10, Exceptional, (251)
"Great place to get away for a quiet stay. Beautiful views of the water and especially at sunset. Lancaster is accessible for fun outings or activities."
United States
Kimberly L.
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Exterior
A working horse farm in Southern Lanc Co., nestled in Amish country.

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

2.0 star property
Holtwood
10.0 out of 10, Exceptional, (24)
"Beautiful place , peaceful, just a breathe of fresh air . They were great and responsive "
United States
julian s.
A working horse farm in Southern Lanc Co., nestled in Amish country.
Terrace/patio
Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake

Perryville
10.0 out of 10, Exceptional, (102)
"Great accommodation overall - would visit again! Calm, great view, perfect spot for a private getaway."
United States
Jörg
Waterfront house with amazing views. Top of the Chesapeake
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
United States
Ashlee S.
The price is ￥49,806
￥92,664 total
includes taxes & fees
Nov 12 - Nov 13
5-bedroom vacation home 5 minutes from historic Charlestown
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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

Port Deposit
10.0 out of 10, Exceptional, (29)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
The price is ￥26,925
￥32,281 total
includes taxes & fees
Nov 19 - Nov 20
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Marina
Waterfront Oasis w/ Private Dock, 3BR/2BA

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

Middle River
9.4 out of 10, Exceptional, (38)
"Quick stay so I could visit family in Abingdon and DC. So awesome. Beautiful property even with the raging wind and snow storm."
United States
Sky S.
Waterfront Oasis w/ Private Dock, 3BR/2BA
Outdoor dining
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

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

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

Perryville
9.2 out of 10, Wonderful, (181)
"Perfect spot for a relaxing weekend on the water, even if the kids are playing in a sports tournament."
United States
Donald R.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Fridge, microwave, oven, stovetop
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.

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

Fawn Grove
9.6 out of 10, Exceptional, (12)
"It was a quiet calm retreat for us to stay during our family time "
United States
Mary R.
The price is ￥34,520
￥52,524 total
includes taxes & fees
Nov 12 - Nov 13
Cozy 2-bedroom cabin in charming Fawn Grove with AC, WIFI & walking trail.
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!

Abingdon
7.6 out of 10, Good, (4)
"We had such a wonderful stay! The house was spotless, comfortable, and beautifully maintained. The surrounding area was peaceful and welcoming, and perfect for a relaxing weekend. Highly recommend!"
United States
Oluwaseyi E.
The price is ￥76,304
￥128,105 total
includes taxes & fees
Nov 13 - Nov 14
Luxury Waterfront Home Built for Entertaining!
Exterior
Chic Towson Retreat: 4BR Getaway Near Baltimore

Chic Towson Retreat: 4BR Getaway Near Baltimore

Towson
9.0 out of 10, Wonderful, (2)
"The place was good , l saw some hair in the second floor bathroom, but otherwise everything was clean. The house very comfortable, they offered complimentary water but was none, I recommend this place but some little things that make the stay better. The address should be sent with more days of anticipation, we stopped at the liquor and we didn’t feel safe."
United States
Elisa M.
Chic Towson Retreat: 4BR Getaway Near Baltimore
Fridge, microwave, oven, stovetop
The River Shack *kayaks*hottub*fishing*quiet*family

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

Airville
9.0 out of 10, Wonderful, (4)
"The gun shots were a little alarming every night."
United States
David W.
The price is ￥20,880
￥64,424 total
includes taxes & fees
Nov 12 - Nov 13
The River Shack *kayaks*hottub*fishing*quiet*family
Interior
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses

2.0 star property
Nottingham
9.6 out of 10, Exceptional, (10)
"It's a rustic but very cozy place. It was very clean and was stocked with so many niceties. Very classy and just lovely. The stairs are kind of steep so you might want to take that into consideration. We walked up to the barn area and met some of the animals - the turkeys and donkeys are quite sociable and very cute! The surrounding area is bucolic. All in all, a really nice place to get away from it all."
United States
LISA L.
The price is ￥24,302
￥36,312 total
includes taxes & fees
Nov 12 - Nov 13
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Fridge, microwave, oven, stovetop
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.

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 house with lots of space for a family gathering. After a couple very hot days at Ripken (only 15 minute drive) the kids enjoyed cooling off in the pool and playing in the large yard. Would definitely stay again! "
United States
melissa d.
The price is ￥124,270
￥206,209 total
includes taxes & fees
Nov 24 - Nov 25
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Terrace/patio
Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome

2.0 star property
Nottingham
The price is ￥26,051
￥81,126 total
includes taxes & fees
Nov 12 - Nov 13
Close to Hospital & White Marsh! Rosedale Townhome
Indoor pool
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

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

White Marsh
10.0 out of 10, Exceptional, (16)
"The host was very nice & accommodating. The house was clean with a beautiful view of the water. I would highly recommend "
United States
Jennifer C.
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

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

Port Deposit
9.8 out of 10, Exceptional, (10)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
The price is ￥20,533
￥32,712 total
includes taxes & fees
Nov 13 - Nov 14
Quarry Landing - Center of Town & River View - 3 Bedroom
Microwave, oven, stovetop
Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC

Aberdeen
9.0 out of 10, Wonderful, (6)
"This was only my second VRBO and I was nervous. The host made it super easy gave me all the details I needed for check in and check out smoothly. Fenced in yard, super nice neighbor and very quiet neighborhood. Gas stove, air fyer and microwave for cooking. Air conditioning will freeze you out, which was wonderful for the 107 degree heat index after a long day on the feild. Very close to Ripken Stadium and lots of food choices! Walmart right next door!"
United States
Sharlee C.
Charming 2-bedroom house in Aberdeen with WiFi and AC
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

Holiday Inn Express Towson - Baltimore North by IHG

Holiday Inn Express Towson - Baltimore North by IHG

10/10 Excellent
"Easy friendly check-in and clean rooms. "
Stephen 1-night trip
Posted 2 days ago
Holiday Inn Express Towson - Baltimore North by IHG

Find out more about Chestnut Hill

Search for holiday rentals in Chestnut Hill on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestnut Hill using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Chestnut Hill?

Yes, you can find vacation rentals close to the most popular sights in Chestnut Hill, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Chestnut Hill?

LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB: This vacation home rental outside of Chestnut Hill is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area.

What are vacation rentals like in Chestnut Hill?

Vacation rentals are private accommodations you can book for a couple days or more in Chestnut Hill. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family trip.