Search Vacation Homes in Chestnut Hill

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Chestnut Hill

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (261)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Beach

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

10.0 out of 10, Exceptional, (234)
"My wife and I had a wonderful time the house was beautiful and the view of the water was incredible. We would definitely stay there again."
LAKE HOUSE, Waterfront Retreat, Eagles, Sunsets on Susquehanna with DOCK
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
Property grounds

Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio

10.0 out of 10, Exceptional, (2)
Serene 3-bedroom waterfront newly renovated house, AC, Fast WiFi, Patio
Luxury Waterfront Home Built for Entertaining!
6 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury Waterfront Home Built for Entertaining!

2.0 out of 10, (1)
The price is AED 2,020
AED 3,293 total
includes taxes & fees
23 Jun - 24 Jun
Luxury Waterfront Home Built for Entertaining!
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

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

9.2 out of 10, Wonderful, (174)
"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
Creekside Cottage is your spacious retreat to enjoy a relaxing getaway!
Property grounds

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

10.0 out of 10, Exceptional, (246)
"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!
5-bedroom vacation home 5 minutes from historic Charlestown
View from property

5-bedroom vacation home 5 minutes from historic Charlestown

9.8 out of 10, Exceptional, (138)
"Can’t wait to come back during warmer weather. It was a perfect over night stay. "
The price is AED 1,318
AED 2,398 total
includes taxes & fees
17 Jul - 18 Jul
5-bedroom vacation home 5 minutes from historic Charlestown
* Beautiful Oasis w/ No Detail Spared *
Smart TV

* Beautiful Oasis w/ No Detail Spared *

9.8 out of 10, Exceptional, (41)
"Amazing location, nice clean place, and a great host.Would recommend "
The price is AED 349
AED 700 total
includes taxes & fees
17 Jul - 18 Jul
* Beautiful Oasis w/ No Detail Spared *
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Smart TV, fireplace

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

The price is AED 863
AED 1,191 total
includes taxes & fees
23 Jul - 24 Jul
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Dock & Hot Tub: Susquehanna River Retreat!
TV, fireplace, books, stereo

Dock & Hot Tub: Susquehanna River Retreat!

9.4 out of 10, Exceptional, (29)
"Wonderful space, beautiful view. Only one issue that was quickly resolved. Would definitely stay there again"
Dock & Hot Tub: Susquehanna River Retreat!
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Property grounds

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

9.4 out of 10, Exceptional, (46)
"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
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
Outdoor dining

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

9.6 out of 10, Exceptional, (56)
"Great place. Accurately depicted in photos. Nice quiet neighborhood. Super dog friendly!"
Cozy home with fenced in yard-Dog Friendly . 2 block walk to historic downtown!
* Stunning New Bungalow Perfect for Everyone *
TV, fireplace, DVD player, books

* Stunning New Bungalow Perfect for Everyone *

9.8 out of 10, Exceptional, (99)
"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 AED 551
AED 1,005 total
includes taxes & fees
13 Jul - 14 Jul
* Stunning New Bungalow Perfect for Everyone *
Your ultimate luxur vacation home
Private kitchen

Your ultimate luxur vacation home

Your ultimate luxur vacation home
The Chalet is located in the woods of a gated property with a covered porch.
Beach

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.
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
" "
Relax in the woods with your own private pool - 4 BR house that sleeps up to 12.
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Smart TV, books, video library

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had an excellent stay"
The price is AED 870
AED 1,232 total
includes taxes & fees
18 Jul - 19 Jul
Winery & Vineyard Mill with 1000+ acres of hiking. Farm with Goats & Horses
Small House on Gentleman’s Farm
Fridge, microwave, oven, stovetop

Small House on Gentleman’s Farm

10.0 out of 10, Exceptional, (11)
"Great little getaway, very clean, and the bedding was so comfy! "
Small House on Gentleman’s Farm
Charming, spacious house with large outdoor area.
Fridge, microwave, oven, stovetop

Charming, spacious house with large outdoor area.

9.6 out of 10, Exceptional, (4)
"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.
Waterfront Retreat with Private Beach and Amazing View on Chesapeake Bay
Outdoor dining

Waterfront Retreat with Private Beach and Amazing View on Chesapeake Bay

9.6 out of 10, Exceptional, (7)
"The home was amazing Had everything we could possibly need for a wonderful stay! Thanks so much "
Waterfront Retreat with Private Beach and Amazing View on 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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