Chestnut Hill Vacation Rentals

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Browse Select Chestnut Hill Vacation Homes

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

9.8 out of 10, Exceptional, (262)
"Amazing place folks. Could not be any better. Thanks again !!!"
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

* 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 CA $214
CA $385 total
includes taxes & fees
Jan 19 - Jan 20, 2025
* Lovely Gem w/ Perfect Combo of Flair & Class *

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (90)
"Owners were responsive. House was immaculate and beds were so comfortable!"
The price is CA $215
CA $393 total
includes taxes & fees
Jan 7 - Jan 8, 2025
* Stunning New Bungalow Perfect for Everyone *

Waters Edge

10.0 out of 10, Exceptional, (114)
"Great!!!"
Waters Edge

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!

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (43)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

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

9.6 out of 10, Exceptional, (29)
"We stayed here over the weekend and had a great time. The home is located about twenty mins from lots of great restaurants and things to do for kids! The arcade machine was a huge hit with my kids. The view of the river was amazing. We sat in the house and watched the sunset and sunrise every day. The host was also very responsive. "
Waterfront Oasis w/ Private Dock, 3BR/2BA

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (19)
"We live in FL and host a small family gathering for Thanksgiving every year. The house was perfect for us and received tons of compliments for location, size and amenities. Thanks for helping us make some wonderful memories!"
Amazing Waterfront Home on the Bush River

Baseball Lovers Paradise!

9.4 out of 10, Exceptional, (6)
"Difficult getting in touch with and not timely responses with host. The house was clean….but the bedspreads and throw pillows need washing. They smell and are very dirty. There were no wash clothes to shower with. The house was not dirty itself. Bathrooms, bedrooms, and kitchen were clean. The location was great for our needs and very close to Ripken. Directions and address to the location need to be better communicated. Overall, I would stay there again and we do travel there a lot. I would...
Baseball Lovers Paradise!

Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"

10.0 out of 10, Exceptional, (100)
"House was great, directions were clear and host provided excellent info, property was absolutely beautiful."
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"

Quiet Bird River Bungalow and Nature Retreat Pet Friendly

10.0 out of 10, Exceptional, (10)
"This was the perfect escape from the city. I was in town for medical appointments and after a long day away, it was nice to come back to a cozy place. The yard was full of beautiful flowers and fun little surprises (we saw frogs, turtles, birds and a groundhog!). The house came fully equipped for anything you might need. Will was very responsive and communicated well. We will definitely put this cute vintage house on the list for our next visit to Maryland."
Quiet Bird River Bungalow and Nature Retreat Pet Friendly

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (13)
"This home is beautifully decorated, making it most inviting and pleasant. The view of the bay was magical! Sitting on the sun porch was so wonderful! The kitchen was the most well equipped kitchen I’ve had the pleasure to use! Thank you for an amazing stay!!"
Upper Chesapeake Getaway - Newly Renovated

A Spacious Haven For Ultimate Comfort 3 Bedroom Home by RedAwning

3.0 star property
A Spacious Haven For Ultimate Comfort 3 Bedroom Home by RedAwning

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

River Haven with Hot Tub | 4 Bed, 3.5 Bath

9.8 out of 10, Exceptional, (23)
"My family stayed here during the week of Thanksgiving. The property is in a very lovely setting, especially in the fall. The size of the house is perfect for a family gathering. Thank you for a lovely stay."
River Haven with Hot Tub | 4 Bed, 3.5 Bath

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!

8-Bedroom Luxury Home in Baltimore County

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 Luxury Home in Baltimore County

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 CA $415
CA $781 total
includes taxes & fees
Dec 29 - Dec 30
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, (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

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (135)
"we had a short stay but wished it was longer, the views from the house and peacefulness of the location were incredible"
The price is CA $286
CA $656 total
includes taxes & fees
Jan 23 - Jan 24, 2025
5-bedroom vacation home 5 minutes from historic Charlestown
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 property types in Chestnut Hill

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

9.8 out of 10, Exceptional, (262)
"Amazing place folks. Could not be any better. Thanks again !!!"
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

Charming cottage overlooking pond and meadows

10.0 out of 10, Exceptional, (53)
"Very cleaned and well designed place, out in the country. We stayed in the winter, but I bet this is a great spot during the warm months as well. Will book again if I’m coming back to the area!"
Charming cottage overlooking pond and meadows

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

10.0 out of 10, Exceptional, (238)
"During Thanksgiving, we walked into a warm house and was greeted with a very well decorated home. Spacious and scenic and remote. My parents are in their 70s so the master bedroom was well placed on the main level. No steps involved. So much stuff to look at in the home. Nice big dining room table for thanksgiving dinner and nice living room for game night. I liked the handwritten notes in the welcome book and the family photos was a nice touch. Nice mix of modern and traditional 30...
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
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.