Search Vacation Homes in Chestnut Hill

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 77 Vacation Homes in Chestnut Hill with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (228)
"We rented the right half of house. Property was clean and right on the lake with hiking trails and boat launch just around each corner. Would definitely stay here again. Only downfall is nearby train goes through often and location is about 30 minutes from shopping and restaurants. Parking at house is only for one small car, others must park in a lot about two houses down the road."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Beautiful Colonial Style Home in Nottingham PA

9.8 out of 10, Exceptional, (11)
"Wonderful experience in a beautiful home. Could live there! Perfect for our entire family. Appreciate how well appointed it was with supplies, linens, etc. Could have used one more bathroom but it didn't cramp our style. Thanks to the host for a memorable vacation! "
Beautiful Colonial Style Home in Nottingham PA

Waters Edge

10.0 out of 10, Exceptional, (125)
"We gathered together children and grandchildren to celebrate Christmas as a family."
Waters Edge

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

9.8 out of 10, Exceptional, (272)
"Stayed here several times. Love it. "
LAKE HOUSE SOUTH Waterfront Retreat with DOCKAGE on Susquehanna River & HOT TUB

Dock & Hot Tub: Susquehanna River Retreat!

9.4 out of 10, Exceptional, (27)
"Wonderful space, beautiful view. Only one issue that was quickly resolved. Would definitely stay there again"
Dock & Hot Tub: Susquehanna River Retreat!

Family Friendly Home w/ Large 1 Acre Backyard & Decks

9.6 out of 10, Exceptional, (13)
"Rented house with our 2 grandkids 6 and 15 for Thanksgiving. They especially loved the yard and it’s an easy drive into Lancaster. Lots of space and great price per night. "
Family Friendly Home w/ Large 1 Acre Backyard & Decks

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (136)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is SARĀ 1,346
SARĀ 2,429 total
includes taxes & fees
8 May - 9 May
5-bedroom vacation home 5 minutes from historic Charlestown

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (98)
"Cute bungalow near Timonium/Lutherville and Towson, very nicely decorated. Comfortable accommodations for our group of 6. Everything we needed and very clean! "
The price is SARĀ 563
SARĀ 1,027 total
includes taxes & fees
15 May - 16 May
* Stunning New Bungalow Perfect for Everyone *

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

9.4 out of 10, Exceptional, (33)
"Clean with comfortable beds!"
Waterfront Oasis w/ Private Dock, 3BR/2BA

Amazing Waterfront Home on the Bush River

10.0 out of 10, Exceptional, (20)
"Wonderful place to stay!"
Amazing Waterfront Home on the Bush River

54 Mi to Dtwn DC: Spacious Family Home!

54 Mi to Dtwn DC: Spacious Family Home!

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

10.0 out of 10, Exceptional, (243)
"This was our second time staying at the property in Drumore. Everyone had a great time and enjoyed our stay. "
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!

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

9.6 out of 10, Exceptional, (56)
"Host was excellent making sure we had everything we needed and more for a comfortable stay. The home was very cozy and comfortable like being in your own home. We will definitely be returning! "
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!

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

9.4 out of 10, Exceptional, (171)
"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

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (96)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake

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

9.6 out of 10, Exceptional, (44)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. šŸ˜ŠšŸ‘ŒšŸ‘"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

Luxury Vacation Home in Towson

2.0 out of 10, (1)
"Stayed with my husband and 2 kids. The house is old, dirty, and the host clearly lied about number of bedrooms. It is 2 bedrooms, not 3. Furniture is old and broken. Pillows are stained. Carpet and entire house is dirty. There was no cleaning prior to our arrival. The kitchen had mops and cleaning supplies out, no trash bags in trashcan. The kitchen was not usable. Overall, it was a terrible stay, would not recommend, will never come back! "
The price is SARĀ 750
SARĀ 1,412 total
includes taxes & fees
4 May - 5 May
Luxury Vacation Home in Towson

Charming, spacious house with large outdoor area.

10.0 out of 10, Exceptional, (2)
"Me and my friends had a great stay at this house over the weekend. The house was clean and comfortable, I’d definitely stay here again!"
Charming, spacious house with large outdoor area.

* Lovely Gem w/ Perfect Combo of Flair & Class *

10.0 out of 10, Exceptional, (52)
"The house was very cozy and in a nice area. Close to all the fun stuff in baltimore we wanted to enjoy!"
The price is SARĀ 559
SARĀ 996 total
includes taxes & fees
4 May - 5 May
* Lovely Gem w/ Perfect Combo of Flair & Class *
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.
Don't see what you're looking for?
See all available properties in Chestnut Hill
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chestnut Hill

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

10.0 out of 10, Exceptional, (228)
"We rented the right half of house. Property was clean and right on the lake with hiking trails and boat launch just around each corner. Would definitely stay here again. Only downfall is nearby train goes through often and location is about 30 minutes from shopping and restaurants. Parking at house is only for one small car, others must park in a lot about two houses down the road."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK

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

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

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

9.8 out of 10, Exceptional, (8)
"Was a charming place to stay close to everything"
The price is SARĀ 731
SARĀ 867 total
includes taxes & fees
5 May - 6 May
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
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.