Chestnut Hill Holiday Rentals

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Holiday Rentals in Chestnut Hill

Our top choices for Chestnut Hill holiday rentals

Waterfront with spectacular view, close to restaurants and bars

9.8 out of 10, Exceptional, (49)
"Would definitely stay again"
Waterfront with spectacular view, close to restaurants and bars

Cheery, Peaceful Water Front Cabin on Winery Grounds

9.8 out of 10, Exceptional, (52)
"Quiet, cozy and private cabin stocked with everything you need!We enjoyed fishing in the pond and dining at High Tides in Colonial Beach.Also visited Westmoreland State Park for hiking & more fishing!We definitely hope to return!"
The price is AU$398
includes taxes & fees
14 Sept - 15 Sept
Cheery, Peaceful Water Front Cabin on Winery Grounds

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

9.8 out of 10, Exceptional, (146)
"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

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

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

10.0 out of 10, Exceptional, (49)
"It was a great place. We enjoyed it."
Large Luxury 4 bed/3 bath Beach House-2 Blocks to beach, 1 Block to Bay

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

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.

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!

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

9.8 out of 10, Exceptional, (13)
"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

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 AU$600
includes taxes & fees
11 Sept - 12 Sept
Large Heated Pool & Hot Tub, Near Quantico DAY Parties and Cookouts Welcome

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

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!

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

Inviting and Serene Home on Monroe Bay Creek

10.0 out of 10, Exceptional, (78)
"This was a fantastic property, well-provisioned, the host was AMAZINGLY responsive and kind after our trip got off to a bit of a rough start. We really enjoyed our stay here!"
Inviting and Serene Home on Monroe Bay Creek

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

10.0 out of 10, Exceptional, (42)
"Very nice, clean and comfortable home. The interior was better than the pictures depicted. Our favorite place was the deck where we watched the ducks and swans. We would definitely come back. "
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

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

10.0 out of 10, Exceptional, (5)
"It was an absolute delight staying at this Colonial Beach rental! From the moment we arrived, we were charmed by its cozy and inviting atmosphere. The house was clean, beautifully decorated, and had everything we needed for a comfortable and relaxing getaway."
Modern 3-bedroom house in Colonial Beach with access to pool and private hot tub

Sail Away

10.0 out of 10, Exceptional, (5)
"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 AU$457
includes taxes & fees
17 Sept - 18 Sept
Sail Away

Peace & Tranquile waterfront home, Colonial Beach

9.8 out of 10, Exceptional, (17)
"Great location"
Peace & Tranquile waterfront home, Colonial Beach

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

10.0 out of 10, Exceptional, (17)
"Great place close to the beach-comfortably fit our family of four. Had some beach stuff we could use as well. Would definitely stay again! "
Charming 2 Bedroom Downtown Vacation Rental: Stroll to Shops and River with Ease

Sunnyside Up - Small Dog Friendly Waterfront Cottage

9.8 out of 10, Exceptional, (20)
"Loved our visit and will definitely be returning!"
Sunnyside Up - Small Dog Friendly Waterfront Cottage
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, 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$398 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?

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.