Chestnut Hill Holiday Rentals

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Our top choices for Chestnut Hill holiday rentals

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (60 reviews)
"Very quiet and great location."
United States
Cindy B.
The price is NZ$468
includes taxes & fees
28 Apr - 29 Apr
Rest & Recharge, A-frame Cabin on Winery Grounds

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, (14 reviews)
"Amazing place, loved it!"
United States
Mike
The price is NZ$786
includes taxes & fees
14 Apr - 15 Apr
The Horseshoe Pond Cabin--15 min to historic Fredericksburg or Kings Dominion VA

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.
The price is NZ$913
includes taxes & fees
13 Apr - 14 Apr
River Refresh - Waterfront with Spa on Placid Bay

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (9 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is NZ$492
includes taxes & fees
15 Apr - 16 Apr
Sail Away

Stunning 90-Acre Home with Pond

Stunning 90-Acre Home with Pond
Caret
The price is NZ$967
includes taxes & fees
13 Apr - 14 Apr
Stunning 90-Acre Home with Pond

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, (12 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.
The price is NZ$571
includes taxes & fees
14 Apr - 15 Apr
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

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

The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.
King George
10.0 out of 10, Exceptional, (2 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 NZ$659
includes taxes & fees
13 Apr - 14 Apr
The ShellHunter getaway at Fairview Beach. The perfect place to disconnect.

Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
10.0 out of 10, Exceptional, (9 reviews)
"Our stay was lovely. Property , location and host were excellent Would definitely book again"
United States
Guðmundur Þór J.
Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Sail Away To

Sail Away To
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"Perfect location and perfect property! The condo was great for our anniversary! The furnishings and amenities were top notch! We would go back again 100%. Recommend renting a golf cart. All of the places to eat are locally owned supporting small business in this community is a great feeling! The owner was so great to communicate with, so very helpful! "
United States
Katherine C.
The price is NZ$496
includes taxes & fees
20 Apr - 21 Apr
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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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 favorite 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 depends 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 NZ$468 per night. Entering your travel dates in the search wizard you might find 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?

Waterfront with spectacular view, close to restaurants and bars: This holiday home rental outside of Chestnut Hill is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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. Monrovia and James Monroe Birthplace 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.