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Compare 65 Vacation Homes in Chestnut Hill with updated reviews, rates, and availability.

Waters Edge
10.0 out of 10, Exceptional, (109)
"This is our 3rd year staying at this house and each year our stay gets better and better. Brian goes out of his way to ensure our stay is “perfect”. He goes to great lengths to make sure the property meets our needs. "
Waters Edge
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!
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
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
Amazing Waterfront Home on the Bush River
10.0 out of 10, Exceptional, (17)
"We stayed here for our wedding weekend leading up to the big day with our families and this couldn't have asked for a better location and place to relax."
Amazing Waterfront Home on the Bush River
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
10.0 out of 10, Exceptional, (217)
"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
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!
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (134)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is AED 1,319
AED 2,398 total
includes taxes & fees
11 Nov - 12 Nov
Top of the Chesapeake - Minutes from Historic Charlestown
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
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"
10.0 out of 10, Exceptional, (99)
"Absolutely gorgeous. Adam and Jodi make certain everything is perfect for your stay. Ideal for nature lovers and those who need to get away and relax. "
Historic Ox Bow House c.1800 "The Cabin at Muddy Creek"
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
9.6 out of 10, Exceptional, (4)
"Loved it here! Highly recommend. "
The price is AED 386
AED 1,129 total
includes taxes & fees
11 Nov - 12 Nov
This house is a 3 bedroom(s), 1.5 bathrooms, located in Port Deposit, MD.
Place to Stay In Airville
9.0 out of 10, Wonderful, (2)
"The property itself was great. Was very clean, the front and backyards were very well done. The only challenges we had were lack of towels and the check-in process. We had a group of seven stay, there were only four towels, and we were not informed to bring additional. The only other challenge was accessing the property - we did not have the access code upon arrival and had to wait longer than anticipated for the owner to respond. These challenges were minor in nature, and our group...
Place to Stay In Airville
A working horse farm in Southern Lanc Co., nestled in Amish country.
2.0 star property
10.0 out of 10, Exceptional, (2)
"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.
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
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
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
9.8 out of 10, Exceptional, (258)
"We had a wonderful stay and had ample space to provide escape when needed and gathering spaces for game time and fellowship. Brian was very attentive to a couple of minor situations and was able to fix them immediately. We all enjoyed the tranquility and view each morning and all the items needed to prepare meals was terrific. We only wished that the fire pit was cleaned out and had smaller logs to burn. Overall we truly enjoyed our stay."
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB
8-bedroom vacation home 28 minutes from Johns Hopkins University
10.0 out of 10, Exceptional, (11)
"This was an ideal and welcoming gathering spot for 12 college friends and spouses for a beautiful Maryland horse country wedding."
8-bedroom vacation home 28 minutes from Johns Hopkins University
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 AED 1,061
AED 2,015 total
includes taxes & fees
10 Nov - 11 Nov
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
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
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

Waters Edge
10.0 out of 10, Exceptional, (109)
"This is our 3rd year staying at this house and each year our stay gets better and better. Brian goes out of his way to ensure our stay is “perfect”. He goes to great lengths to make sure the property meets our needs. "
Waters Edge
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
10.0 out of 10, Exceptional, (217)
"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
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
10.0 out of 10, Exceptional, (234)
"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!
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.