Chestnut Hill Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chestnut Hill holiday rentals

A wooden cabin with a balcony, surrounded by lush greenery and trees.

1. Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (76 reviews)
"Always a great stay! "
United States
Amy H.
The price is AU$356
includes taxes & fees
1 Dec - 2 Dec
Rest & Recharge, A-frame Cabin on Winery Grounds
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

2. 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, (17 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is AU$459
includes taxes & fees
18 Nov - 19 Nov
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A two-story house with a front deck and a garage.

3. 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, (17 reviews)
"The cottage was so clean and decorated so perfect for the location- easy walk to river - would stay again"
United States
Debra W.
The price is AU$531
includes taxes & fees
19 Nov - 20 Nov
The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.
A small, single-story house with a red door, a porch with white railings, and a brick pathway leading to the entrance.

4. 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
8.4 out of 10, Very good, (5 reviews)
"Charming cottage with updated decor. The host was very comucative during a power outage due to storms. The kitchen was nicly stocked with snacks and drinks. The pool was nice, but the backyard was not very usable due to some leftovers from repair work taking up the grassy area."
United States
Kelley M.
The price is AU$344
includes taxes & fees
15 Nov - 16 Nov
Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD
A waterfront hotel with a dock extending into the water, a large building with multiple floors, and a clear sky.

5. Sail Away To

Sail Away To
Colonial Beach
9.6 out of 10, Exceptional, (18 reviews)
"Easy check-in, great location. The place was very comfortable and a short walk to everything. Great view from the balcony."
United States
Tina S.
The price is AU$395
includes taxes & fees
13 Nov - 14 Nov
Sail Away To
A beach with a palm tree, a pier, and the sun in the sky.

6. The Sugar Shack - charming, fully renovated 1930s cottage with AC

The Sugar Shack - charming, fully renovated 1930s cottage with AC
Colonial Beach
The price is AU$464
includes taxes & fees
7 Dec - 8 Dec
The Sugar Shack - charming, fully renovated 1930s cottage with AC
A wooden gazebo with benches, a yellow-painted floor, and a view of the ocean.

7. Available for Winter Festival/Firepit/Grill/One Level

Available for Winter Festival/Firepit/Grill/One Level
Colonial Beach
10.0 out of 10, Exceptional, (7 reviews)
"This was such a lovely place with lots of room and it was close to the beach too. I plan to come back soon."
United States
Cynthia H.
The price is AU$681
includes taxes & fees
12 Nov - 13 Nov
Available for Winter Festival/Firepit/Grill/One Level
A balcony with a white railing, outdoor furniture, and a view of the sea.

8. Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (14 reviews)
"we liked everything and location!!!"
United States
Shawn
The price is AU$397
includes taxes & fees
30 Nov - 1 Dec
Sail Away
A modern living room with a large flat-screen TV mounted on a wooden wall with a chevron pattern. There is a fireplace below the TV, a console table with decorative items, and two potted plants.

9. Modern Private Lowerlevel Suite Free Parking + Wi-Fi, close to Quantico

Modern Private Lowerlevel Suite Free Parking + Wi-Fi, close to Quantico
Stafford
10.0 out of 10, Exceptional, (2 reviews)
"Great stay! Very clean, comfortable, and has everything you could need."
United States
Tara S.
The price is AU$346
includes taxes & fees
29 Nov - 30 Nov
Modern Private Lowerlevel Suite Free Parking + Wi-Fi, close to Quantico
A deck with outdoor furniture overlooking a lake.

10. River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is AU$725
includes taxes & fees
21 Nov - 22 Nov
River Refresh - Waterfront with Spa on Placid Bay
A spacious living room with a beige sofa, a patterned ottoman, and a dining area with a table and chairs.

11. 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, (11 reviews)
"The host was communicative and helpful. Amenities were great and lay out of the space was inviting. "
United States
Bili M.
The price is AU$552
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom bungalow in Quantico Town 2 King Beds Game Room Entire Home!
A spacious living room with a green sofa, glass coffee tables, and a fireplace. A staircase with a railing leads to an upper level.

12. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
10.0 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay at this property and will definitely be back again!"
United States
Jeff and Nancy B.
The price is AU$815
includes taxes & fees
16 Nov - 17 Nov
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
A kitchen with white cabinets, a stainless steel refrigerator, a checkered island, and a two-tiered serving tray.

13. 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 AU$1,797
includes taxes & fees
16 Nov - 17 Nov
43 acre private retreat for the whole family within minutes of DC
A modern kitchen with a large island, white cabinetry, and a teal accent wall.

14. 5 BR King Beds Game Room Yard Family Home Explore DC Quantico Stafford

5 BR King Beds Game Room Yard Family Home Explore DC Quantico Stafford
Stafford
9.8 out of 10, Exceptional, (29 reviews)
"Great location for our family of 6 to visit our Marine. The house fit us so comfortably, it was very clean and located conveniently to so many stores, restaurants, base and museum with reasonable drive to DCA. Would definitely recommend."
United States
Julie d.
The price is AU$915
includes taxes & fees
30 Nov - 1 Dec
5 BR King Beds Game Room Yard Family Home Explore DC Quantico Stafford
A hallway with a wooden floor, a white wall, and a ceiling with a central light fixture. There is a door on the left and a mirror on the right.

15. Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
La Plata
9.6 out of 10, Exceptional, (4 reviews)
"Cane for a weekend of Faith and Fun and this is exactly what we needed. Comfortably suited our 10 needs and so much more. Peaceful, serene, beautiful animals, game room, so much to say. Hostess with the mostest!!!! Charity is a gem! My church family will be back!!!!!"
United States
Wadiya D.
The price is AU$1,171
includes taxes & fees
18 Nov - 19 Nov
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
A two-story log cabin with a covered garage, a large driveway, and a scenic view of trees and sky.

16. The Black Log Cabin - Hot Tub & Game Room

The Black Log Cabin - Hot Tub & Game Room
Fredericksburg
8.0 out of 10, Very good, (2 reviews)
"Fun, lots to do with kids!"
United States
Cecilia P.
The Black Log Cabin - Hot Tub & Game Room
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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Find out more about Chestnut Hill

Everything you need to know about Chestnut Hill holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestnut Hill holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Chestnut Hill holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestnut Hill holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestnut Hill holiday rentals we have selected for you start as low as AU$343 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chestnut Hill rentals

At Expedia, we put the best Chestnut Hill holiday 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 holiday.

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 holiday rental in Chestnut Hill?

Yes, there are holiday rentals close to the most popular sights in Chestnut Hill, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chestnut Hill has to offer?

Private Retreat Bungalow-One Level, 2 blocks from Beach w/Porch & Deck: This holiday 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 that you can cook with friends or family. Make the most 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. Caledon State Park and Bayside Marina are a couple of places you'll find in the wider area.

What are holiday rentals like in Chestnut Hill?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chestnut Hill. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.