Chestnut Hill Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestnut Hill vacation rentals

Cheery, Peaceful Water Front Cabin on Winery Grounds

Cheery, Peaceful Water Front Cabin on Winery Grounds
Colonial Beach
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

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing
Newburg
9.8 out of 10, Exceptional, (155)
"Lovely place and location!"
United States
Christa W.
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown
Colonial Beach
9.8 out of 10, Exceptional, (19)
"So convenient to the beach and downtown Colonial Beach restaurants and shopping. We will definitely be back! "
United States
Marisa Z.
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Luxurious 3 Bedroom Riverfront Condo with Private Deck

Luxurious 3 Bedroom Riverfront Condo with Private Deck
2.0 star property
Colonial Beach
10.0 out of 10, Exceptional, (13)
"Beautiful place and very clean will be going back next uear"
United States
Connie S.
Luxurious 3 Bedroom Riverfront Condo with Private Deck

Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome

Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome
Stafford
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

Smallwood St Park, Groups, Fire Pit, Blackstone, large parking area

Smallwood St Park, Groups, Fire Pit, Blackstone, large parking area
Marbury
9.6 out of 10, Exceptional, (29)
"Great place to stay! Quiet neighborhood, very clean and spacious with lots of room for guests to have their own beds. Highly recommend!"
United States
Michelle H.
Smallwood St Park, Groups, Fire Pit, Blackstone, large parking area

Sunnyside Up - Small Dog Friendly Waterfront Cottage

Sunnyside Up - Small Dog Friendly Waterfront Cottage
Colonial Beach
10.0 out of 10, Exceptional, (23)
"Very comfortabe with excellent location."
United States
Ray W.
Sunnyside Up - Small Dog Friendly Waterfront Cottage

3-bedroom quiet countryside house in charming Fredericksburg 2 King Beds

3-bedroom quiet countryside house in charming Fredericksburg 2 King Beds
Fredericksburg
10.0 out of 10, Exceptional, (3)
"Such a perfect little house! We stayed for 3 weeks while moving and we really enjoyed our stay. "
United States
Laina J.
3-bedroom quiet countryside house in charming Fredericksburg 2 King Beds

Crab Shack in Town-Walk to beach and restaurants-Sleeps 6

Crab Shack in Town-Walk to beach and restaurants-Sleeps 6
Colonial Beach
9.6 out of 10, Exceptional, (17)
"Great location, super clean and cute decor! Appreciated the toothbrush holders in bathrooms. 10/10 would recommend Crab Shack! "
United States
Eve H.
Crab Shack in Town-Walk to beach and restaurants-Sleeps 6

Cozy one bedroom w/private bathroom with WiFi, pool, fitness room

Cozy one bedroom w/private bathroom with WiFi, pool, fitness room
King George
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

Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay
Colonial Beach
10.0 out of 10, Exceptional, (50)
"It was very nice. Second visit to this house. Very clean and well thought out for guests. "
United States
Patricia H.
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.
Maddox
10.0 out of 10, Exceptional, (16)
"Chris and his wife Lynda were absolutely amazing. They included us in their activities and showed us around a bit. We now consider them family! Super prompt with questions, activities, and information about the surrounding area! Loved every minute of our time at the cottage. "
United States
Kim K.
Waterfront Sunsets, Fishing, Boating, and Crabs! Paxs River, Budds Creek MIR.

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub
Colonial Beach
10.0 out of 10, Exceptional, (8)
"Our host was the absolute bestThis was our first time using a VRBO property! The host answered all our questions and even provided excellent recommendations for restaurants and other activities in the area.Overall a great experience, we are hooked on the VRBO experience."
United States
Buster H.
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach Cottage, 7 minutes walk to beach!
Colonial Beach
9.2 out of 10, Wonderful, (35)
"Easy check in, over all nice place with a very convenient location. Property owner VERY responsive and excellent. We had a great 3 night 4 day stay."
United States
Kye H.
Colonial Beach Cottage, 7 minutes walk to beach!

Peace & Tranquile waterfront home, Colonial Beach

Peace & Tranquile waterfront home, Colonial Beach
Colonial Beach
9.8 out of 10, Exceptional, (18)
"Great place.We really enjoyed our stay. Fishing was pretty good and we used the kayaks just about everyday.Thank you for the life jackets. Also a family of swans would visit us daily.Great communication.No complaints and we would definitely stay again in the future. "
United States
john y.
Peace & Tranquile waterfront home, Colonial Beach

Charming 2 Bedroom Downtown Vacation Rental: Stroll to Shops and River with Ease

Charming 2 Bedroom Downtown Vacation Rental: Stroll to Shops and River with Ease
Colonial Beach
10.0 out of 10, Exceptional, (18)
"Great stay and location."
United States
Peter T.
Charming 2 Bedroom Downtown Vacation Rental: Stroll to Shops and River with Ease

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, (60)
"Wonderful stay, house was great and close to to everything "
United States
Leigh D.
Waterfront with spectacular view, close to restaurants and bars

Sail Away

Sail Away
Colonial Beach
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

Blue Heron Cottage is cozy & convenient. Renovated March 2023!

Blue Heron Cottage is cozy & convenient. Renovated March 2023!
Colonial Beach
10.0 out of 10, Exceptional, (52)
"This is our second year staying in this beautiful cottage - just perfect for the three of us! Would highly recommend! "
United States
Kellie W.
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

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, (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
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.
Save an average of 15% on thousands of hotels when you're signed in

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.