Holiday Rentals in Chestnut Hill

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Holiday Rentals in Chestnut Hill

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (51)
"Great stay and peaceful spot. "
The price is €200
includes taxes & fees
8 Sept - 9 Sept
Cheery, Peaceful Water Front Cabin on Winery Grounds

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

9.8 out of 10, Exceptional, (144)
"We enjoyed our stay at the waterfront cottage with yoga on the dock in the morning, afternoon kayaking and dinner at Captain Billy’s Seafood restaurant. Down time spent reading and nature watching made the for the perfect weekend."
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Sail Away

10.0 out of 10, Exceptional, (4)
"Loved the View from inside the condo and on the balcony. Has everything you need and is new and clean. Right on the boardwalk with beach and res"
The price is €265
includes taxes & fees
3 Sept - 4 Sept
Sail Away

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

9.8 out of 10, Exceptional, (19)
"Very clean, great location, and comfortable beds, we had a great time. Walking distance to bars, restaurants, and coffee shops. Very convenient, and the owner was easy to work with. "
Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown

Charming 3-bedroom house with WiFi, AC in delightful Colonial Beach

10.0 out of 10, Exceptional, (7)
"Host provided everything needed and very responsive. Truly enjoyed our stay and the area. "
Charming 3-bedroom house with WiFi, AC in delightful Colonial Beach

Waterfront with spectacular view, close to restaurants and bars

10.0 out of 10, Exceptional, (44)
"Everything was great. "
Waterfront with spectacular view, close to restaurants and bars

This cabin is a 3 bedroom(s), 3 bathrooms, located in Fredericksburg, VA.

9.4 out of 10, Exceptional, (36)
"The property was as advertised and clean. Had an issue with air conditioning. Need to supply soap and shampoo. Overall good place."
This cabin is a 3 bedroom(s), 3 bathrooms, located in Fredericksburg, VA.

3-bedroom house in charming Colonial Beach with AC, WiFi

10.0 out of 10, Exceptional, (4)
"- house was great!- AC worked great!- our kids loved the crayons and all the kids toys!- highly recommend to stay here!"
3-bedroom house in charming Colonial Beach with AC, WiFi

An upscale retreat across from the beach

An upscale retreat across from the beach

Charming 1-bedroom house with AC and WiFi in quaint Montross

10.0 out of 10, Exceptional, (10)
"Great time in the home! Pat was lovely and very helpful. Whenever I am back in the area, I will stay here again!"
The price is €228
includes taxes & fees
15 Sept - 16 Sept
Charming 1-bedroom house with AC and WiFi in quaint Montross

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (77)
"We enjoyed our stay at this lovely property. The house is very well appointed, incredibly clean and designed for groups to enjoy their time together. Owner was very responsive and kind. "
Inviting and Serene Home on Monroe Bay Creek

Colonial Beach Cottage, 7 minutes walk to beach!

9.2 out of 10, Wonderful, (32)
"We can me in town for our daughter’s graduation and chose this home bc it was more space, provided a cozy/updated feel and right next to restaurants, the beach and hiking trails! We would definitely stay here again for our next visit! "
Colonial Beach Cottage, 7 minutes walk to beach!

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (16)
"Great place! "
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Downtown Residential Suite across from the Beach

10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay. Well decorated, peaceful, adjacent to the beach and dining. "
Downtown Residential Suite across from the Beach

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

10.0 out of 10, Exceptional, (52)
"As advertised, had a great time!"
Blue Heron Cottage is cozy & convenient. Renovated March 2023!

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

9.8 out of 10, Exceptional, (93)
"Ricky is a great and friendly host. The stay very relaxing and fun. "
The price is €434
includes taxes & fees
28 Aug - 29 Aug
Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome

Cottage on The Point! Bring your bikes & golf cart, and your pets!

10.0 out of 10, Exceptional, (30)
"Nice little beach cottage with a great host. Just a few blocks from the beach. Would stay again!"
Cottage on The Point! Bring your bikes & golf cart, and your pets!

Sunnyside Up - Small Dog Friendly Waterfront Cottage

9.8 out of 10, Exceptional, (20)
"My wife and I truly enjoyed our stay in colonial Beach! The cabin was very nicely decorated and furnished a well equipped kitchen, and we had great conversation via messaging in person with the owners of the property. We would definitely stay there again."
Sunnyside Up - Small Dog Friendly Waterfront Cottage

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

10.0 out of 10, Exceptional, (12)
"An absolutely beautiful stay, Jennifer was easy to communicate with. Enjoyed every bit of it. It is a bit tucked away from main roads but nothing too crazy."
5 BR King Beds Game Room Yard Family Home Explore DC Quantico Stafford

Luxurious 3 Bedroom Riverfront Condo with Private Deck

2.0 star property
10.0 out of 10, Exceptional, (12)
"this lovely condo was right in the middle of everything. Very nice and really clean! thoroughly enjoyed our stay!"
Luxurious 3 Bedroom Riverfront Condo with Private Deck
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

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, apart-hotels, 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 €200 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. 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.