Chestnut Hill Vacation Rentals

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Our top choices for Chestnut Hill vacation rentals

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
$327 nightly
The price is $364
May 28 - May 29
Total with taxes and fees
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (62 reviews)
"Always a great stay! "
United States
Amy H.
$239 nightly
The price is $260
May 26 - May 27
Total with taxes and fees
Rest & Recharge, A-frame Cabin on Winery Grounds

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

The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.
King George
9.6 out of 10, Exceptional, (4 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.
$376 nightly
The price is $415
May 26 - May 27
Total with taxes and fees
The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.

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
$421 nightly
The price is $464
May 25 - May 26
Total with taxes and fees
The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA

Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD
King George
$255 nightly
The price is $281
May 31 - Jun 1
Total with taxes and fees
Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

Charming 3-bedroom bungalow in Quantico Town 2 King Beds Game Room Entire Home!

Charming 3-bedroom bungalow in Quantico Town 2 King Beds Game Room Entire Home!
Quantico
10.0 out of 10, Exceptional, (6 reviews)
"The host was communicative and helpful. Amenities were great and lay out of the space was inviting. "
United States
Bili M.
$287 nightly
The price is $327
Jun 15 - Jun 16
Total with taxes and fees
Charming 3-bedroom bungalow in Quantico Town 2 King Beds Game Room Entire Home!

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (22 reviews)
"Fantastic amenities, beautiful view, cosy yet spacious!"
United States
Aaron M.
$488 nightly
The price is $531
May 27 - May 28
Total with taxes and fees
River Refresh - Waterfront with Spa on Placid Bay

Stunning 90-Acre Home with Pond

Stunning 90-Acre Home with Pond
Caret
$519 nightly
The price is $578
May 23 - May 24
Total with taxes and fees
Stunning 90-Acre Home with Pond

Private Waterfront Retreat w/ dock on 7+ acre

Private Waterfront Retreat w/ dock on 7+ acre
Colonial Beach
$713 nightly
The price is $776
May 28 - May 29
Total with taxes and fees
Private Waterfront Retreat w/ dock on 7+ acre

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (10 reviews)
"Stay was wonderful!"
United States
Karen H.
$309 nightly
The price is $313
May 27 - May 28
Total with taxes and fees
Sail Away

Sail Away To

Sail Away To
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"We stayed two nights June 11-13 and it is an excellent VRBO, clean, great location, great views, good parking space, with washer and dryer. The hosts are super, welcoming, and responsive. Highly recommended."
United States
James T.
$312 nightly
The price is $316
May 26 - May 27
Total with taxes and fees
Sail Away To
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

Everything you need to know about Chestnut Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestnut Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestnut Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestnut Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chestnut Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $260 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chestnut Hill rentals

At Expedia, we put the best Chestnut Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestnut Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestnut Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestnut Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck: This vacation home rental outside of Chestnut Hill is located on the beach and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.