Chestnut Hill Holidays from £1,973

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    Packages with flights are ATOL protected

Top Chestnut Hill Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

2.5 out of 5
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Property in secluded area. Nice landscape

Reviewed on 5 Aug 2025

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,009 reviews)
Everything was top notch. You don’t find this service and attention to detail anymore,

Reviewed on 7 Aug 2025

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9/10 Wonderful! (1,824 reviews)
Excellent location for downtown and Acadamy access. Really enjoyed the history of the location and the displays. Staff was wonderful!

Reviewed on 7 Aug 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,002 reviews)
We had a wonderful stay at THE GRADUATE. We will definitely return when we visit Annapolis.

Reviewed on 6 Aug 2025

The Ivy Hotel

The Ivy Hotel

5 out of 5
Midtown
per person
30 Oct - 6 Nov
found 1 day ago
Return direct flight included
London (LON) to Baltimore (BWI)
10/10 Exceptional! (181 reviews)
My husband and I travel all around the world. We decided to celebrate his milestone birthday and retirement at The Ivy, which had been on our bucket list for a while. My goodness! It's the best hotel we've ever visited. If there were such a thing as a six star hotel, this would be it. The rooms, the luxurious touches, the service, the thoughtful design, the food, the ammenities--all perfection. No detail was overlooked. Everyone on the staff greeted us by name. Their car service was able to take us anywhere witinin a 3-mile radius, so we were able to valet park on arrival and not have to drive anywhere ourselves until we left. They have a no tipping policy. The room is stocked with wine, coffee, tea, local beers, sparkling water, etc. (all complimentary). They anticipated our needs and made our stay magical. We hope to return soon. Shout out to our servers, Anthony, April, and Jackie; our driver Chris; our consierge James. Well done one and all.

Reviewed on 7 Jul 2025

Chestnut Hill Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
4ºC
Max Temp Summer
27ºC

Top hotels in Chestnut Hill

Holiday Inn Express Towson - Baltimore North by IHG

Holiday Inn Express Towson - Baltimore North by IHG

2.5 out of 5
1100 Cromwell Bridge Rd, Towson, MD
Fully refundable
The price is £105 per night from 31 Aug to 1 Sept
£105
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,034 reviews)
"Nice location, clean and quiet."

Reviewed on 3 Aug 2025

Holiday Inn Express Towson - Baltimore North by IHG
Comfort Inn Baltimore East Towson

Comfort Inn Baltimore East Towson

2.5 out of 5
8801 Loch Raven Blvd, Parkville, MD
Fully refundableReserve now, pay when you stay
The price is £61 per night from 14 Aug to 15 Aug
£61
14 Aug - 15 Aug
includes taxes & fees
6/10 (1,000 reviews)
"It was great for me and my wife"

Reviewed on 22 Jul 2025

Comfort Inn Baltimore East Towson
Embassy Suites by Hilton Baltimore Hunt Valley

Embassy Suites by Hilton Baltimore Hunt Valley

3.5 out of 5
213 International Cir, Cockeysville, MD
Fully refundableReserve now, pay when you stay
The price is £123 per night from 5 Sept to 6 Sept
£123
5 Sept - 6 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"The property was in a quiet area and it was across from a shopping center that really came in handy."

Reviewed on 1 Aug 2025

Embassy Suites by Hilton Baltimore Hunt Valley
See all 282 properties in Chestnut Hill
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.
All Inclusive Holidays
All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Chestnut Hill travel package cost?
We make it simple to see the world, with Chestnut Hill travel packages starting from as little as £1,973. You'll have the flexibility to combine your favourite airlines, hotels and car rental. For the ultimate escape, why not add some experiences and tours to your itinerary?
If I'm not able to travel, can I cancel my Chestnut Hill travel package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Chestnut Hill travel package in the last 24 hours? You may be able to make any changes for free. For bookings older than that, you may incur a charge from your airline, hotel or car rental company. For more information, take a look at our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to Chestnut Hill?
You'll save big if you combine your car rentals, hotels and flights into a Chestnut Hill travel package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 properties worldwide, which means you'll always have plenty of variety to choose from. Want to save even more? Add some popular activities to your package deal and unlock even more discounts! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Chestnut Hill holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Don't forget to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: If you'd like to pay off your getaway across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this payment option. Simply put down a small deposit on your holiday and then get on your way.

How far in advance should I book my Chestnut Hill holiday?
Earlier is always better. Airlines generally advertise flights up to 12 months prior to departure, and this is a great opportunity to pick up some rock-bottom prices. Just been told you should take all your holiday days next month? No need to worry. Expedia are never short on fantastic deals to whisk you away on the getaway of your dreams, at an affordable price.
What does an Expedia Chestnut Hill travel package include?
From flights and hotels to rental cars, Expedia can help you create a Chestnut Hill package that's ideal for you. Holidaying for a few weeks? Consider a hotel, rental car and flight bundle. If you're taking a short break, an airfare and hotel deal could suit you better. Tours and activities can be added once you've made your booking. Our travel packages make it a breeze to plan and save.
What should I know before booking a Chestnut Hill travel package?
You'll land terrific savings when you combine your flights, hotels and rental cars into a travel package. Plus, booking everything together makes trip planning easier. So why waste your money or time? Whether you're organising a ritzy romantic getaway or a low-cost family road trip, check out our travel packages today.
Can I choose my airline with a Chestnut Hill Expedia travel package?
With a travel package, you're in charge. Whether you're eager to fly to Chestnut Hill in business or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines across the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.