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Chestnut Hill Vacation Rentals

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Our top choices for Chestnut Hill vacation rentals

Charming 6BR Colonial Beach Retreat, Walk to the Beach

Charming 6BR Colonial Beach Retreat, Walk to the Beach
Colonial Beach
The price is CA $739
CA $1,435 total
includes taxes & fees
Jul 15 - Jul 16
Charming 6BR Colonial Beach Retreat, Walk to the Beach

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (67 reviews)
"Always a great stay! "
United States
Amy H.
The price is CA $207
CA $431 total
includes taxes & fees
Aug 3 - Aug 4
Rest & Recharge, A-frame Cabin on Winery Grounds

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is CA $354
CA $758 total
includes taxes & fees
Jul 16 - Jul 17
River Refresh - Waterfront with Spa on Placid Bay

Waterfront with spectacular view, close to restaurants and bars

Waterfront with spectacular view, close to restaurants and bars
Colonial Beach
9.8 out of 10, Exceptional, (73 reviews)
"We had a wonderful stay in this clean, beautiful waterfront property. The location was fantastic, and we loved watching the swan and osprey go about their days from the front porch. We were two couples (ages 45-75!), and the place and town were the perfect, relaxing getaway. "
United States
Alexis V.
Waterfront with spectacular view, close to restaurants and bars

The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA

The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA
Woodford
10.0 out of 10, Exceptional, (16 reviews)
"Amazing place, loved it!"
United States
Mike
The price is CA $309
CA $657 total
includes taxes & fees
Jul 27 - Jul 28
The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA

43 acre private retreat for the whole family within minutes of DC

43 acre private retreat for the whole family within minutes of DC
Nanjemoy
10.0 out of 10, Exceptional, (2 reviews)
"Great place, very private with expansive outdoor space. Host were very accommodating. Will definitely book again."
United States
Khanh N.
The price is CA $1,524
CA $2,355 total
includes taxes & fees
Jul 20 - Jul 21
43 acre private retreat for the whole family within minutes of DC

Sail Away To

Sail Away To
Colonial Beach
9.4 out of 10, Exceptional, (14 reviews)
"The apartment was beautiful. he location made it easy to get around. Being able up front to the bay was awesome. Had my morning coffee on the deck."
United States
Christina
The price is CA $292
CA $558 total
includes taxes & fees
Aug 11 - Aug 12
Sail Away To

The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.

The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.
King George
9.8 out of 10, Exceptional, (8 reviews)
"We had a great stay. We were there to see my son and grandson for the week. The property is in a quiet neighborhood. We enjoyed the local restaurant. Shelly was very responsive to our inquiries. We would definitely stay there again."
United States
Sean R.
The price is CA $282
CA $620 total
includes taxes & fees
Aug 9 - Aug 10
The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"This place is fantastic!!Great responsive owners! Fantastic location, perfectly stocked kitchen, comfy beds and bar none the cleanest place I’ve stayed!! The house is adorable and comfortable with a rocking fire pit. The location is walkable and yet quiet!Stay here!No notes!!"
United States
Amanda M.
The price is CA $269
CA $655 total
includes taxes & fees
Aug 12 - Aug 13
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly

The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly
Colonial Beach
10.0 out of 10, Exceptional, (16 reviews)
"House was amazing. we are staying out of town for work and have stayed in 5 other houses so far and this is the best one yet by far "
United States
Kyle M.
The price is CA $963
CA $1,645 total
includes taxes & fees
Jul 26 - Jul 27
The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly

Sail Away

Sail Away
Colonial Beach
10.0 out of 10, Exceptional, (12 reviews)
"we liked everything and location!!!"
United States
Shawn
The price is CA $313
CA $584 total
includes taxes & fees
Aug 2 - Aug 3
Sail Away
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

Find out more about Chestnut Hill

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chestnut Hill. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Chestnut Hill?

Yes, we give you a choice of vacation rentals near top attractions in Chestnut Hill, or you can go with a more secluded option if you want a relaxing place to stay.

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

The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.: This vacation home rental outside of Chestnut Hill offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

What can I see and do in Chestnut Hill?

While you're exploring the area, Colonial Beach and Westmoreland State Park are a couple of picturesque spots to get outside and enjoy nature. Bayside Marina and Colonial Beach Historical Society 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 reserve for a few days or a quick weekend in Chestnut Hill. Vacation rentals offer amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.