Chestnut Hill Vacation Rentals

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Our top choices for Chestnut Hill vacation rentals

9.8 out of 10, Exceptional, (56)
"Very quiet and great location."
United States
Cindy B.
$172 nightly
The price is $187
Dec 14 - Dec 15
Total with taxes and fees
Cheery, Peaceful Water Front Cabin on Winery Grounds
9.2 out of 10, Wonderful, (10)
"We had a wonderful stay at this home. It is very well kept and taken care of. Beautiful property and the owners are very responsive. Thank you for a wonderful visit!!! We look forward to staying again!!!"
United States
Kristin R.
$269 nightly
The price is $299
Dec 14 - Dec 15
Total with taxes and fees
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
10.0 out of 10, Exceptional, (1)
$121 nightly
The price is $134
Dec 14 - Dec 15
Total with taxes and fees
Cozy one bedroom w/private bathroom with WiFi, pool, fitness room

Apartment in Colonial Beach

Sail Away
9.8 out of 10, Exceptional, (9)
"Very clean and well kept. Pictures were accurate. I would stay here again. "
United States
Anne
$285 nightly
The price is $289
Dec 14 - Dec 15
Total with taxes and fees
Sail Away
$149 nightly
The price is $164
Dec 14 - Dec 15
Total with taxes and fees
Enjoyable 3-bedroom house in King George. 5 mins to Dahlgren Naval Base
$421 nightly
The price is $446
Dec 19 - Dec 20
Total with taxes and fees
Charming 2-bedroom cottage in wonderful Newburg with WiFi, AC
10.0 out of 10, Exceptional, (12)
"We really enjoyed our stay. The property is ao nice with the firepit and pond. House was clean and neatly decorated. "
United States
Brian W.
$418 nightly
The price is $461
Dec 14 - Dec 15
Total with taxes and fees
The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA
10.0 out of 10, Exceptional, (20)
"Spectacular place, fenomenal view, peaceful and quiet on fall season. We’re definitely coming back. Highly recommend. "
United States
Joyce
$470 nightly
The price is $511
Dec 14 - Dec 15
Total with taxes and fees
River Refresh - Waterfront with Spa on Placid Bay

Apartment in Colonial Beach

Sail Away To
9.4 out of 10, Exceptional, (12)
"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.
$286 nightly
The price is $290
Dec 15 - Dec 16
Total with taxes and fees
Sail Away To
9.8 out of 10, Exceptional, (15)
"We love going to Colonial Beach. This house offered everything we were looking for in a mini vacation."
United States
Anonymous traveler
$404 nightly
The price is $450
Jan 4 - Jan 5, 2026
Total with taxes and fees
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
9.8 out of 10, Exceptional, (93)
"Ricky is a great and friendly host. The stay very relaxing and fun. "
United States
Cody B.
$361 nightly
The price is $420
Dec 14 - Dec 15
Total with taxes and fees
Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome
10.0 out of 10, Exceptional, (14)
"This house is lovely with the host being amazing. All of our questions were answered with a friendly response.The location to the water, shops, and restaurants is perfect. "
United States
LaVerne P.
$713 nightly
The price is $794
Dec 22 - Dec 23
Total with taxes and fees
The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly

Vacation Home in Caret

Stunning 90-Acre Home with Pond
$519 nightly
The price is $578
Jan 1 - Jan 2, 2026
Total with taxes and fees
Stunning 90-Acre Home with Pond

Vacation Home in Colonial Beach

4-bedroom house in wonderful Colonial Beach
$547 nightly
The price is $609
Jan 13 - Jan 14, 2026
Total with taxes and fees
4-bedroom house in wonderful Colonial Beach
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 $134 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?

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown: This vacation home rental outside of Chestnut Hill is on a river and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Chestnut Hill?

While you're exploring the area, Colonial Beach and Crow's Nest Natural Area Preserve are a couple of picturesque spots to get outside and enjoy nature. Caledon State Park and Bayside Marina 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.