Chelmsford Holidays
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Chelmsford Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
West End
S$1,924
per person
16 Oct - 18 Oct
found 11 hours ago
Return direct flight included
Stillwater (SWO) to Boston (BOS)
8.8/10 Excellent! (1,566 reviews)
Charming small hotel close to the North End : an 8 minute walk from great food and MBTA the train station. Rooms are small but very comfortable and well-appointed. Staff was welcoming and helpful. Excellent breakfast.
Reviewed on 27 Aug, 2026
Omni Parker House
Downtown Boston
S$2,000
per person
16 Oct - 18 Oct
found 11 hours ago
Return direct flight included
Stillwater (SWO) to Boston (BOS)
9/10 Wonderful! (3,711 reviews)
The hotel has real charm to it. The rooms have been updated and are spacious. I love the location as we were able to walk to places like Fanueil Hall/Quincy Market Place, the North End, the Boston Common, Public Gardens and Copley Square. Enjoyed spending time in the historic Last Hurrah.
Reviewed on 27 Aug, 2026
Top hotels in Chelmsford
Holiday Inn Express Chelmsford by IHG
8 Independence Drive Chelmsford MA
Fully refundableReserve now, pay when you stay
S$156
30 Aug - 31 Aug
includes taxes & fees
Encore Boston Harbor
1 Broadway Everett MA
S$407
21 Sept - 22 Sept
includes taxes & fees
9.6/10 Exceptional! (4,113 reviews)
"We had 3 rooms booked under a reservation and the hotel messed up and only checked in 2 even though it clearly said 3. One guy was very helpful, made a note on the account that things were fixed and when we arrived at night The front desk staff(specifically the manager) were rude in trying to get ..."
Reviewed on 27 Aug, 2026
Arcadian Hotel
1200 Beacon St Brookline MA
Fully refundableReserve now, pay when you stay
S$313
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (4,408 reviews)
"Would be nice if they can make the bathtub less slippery"
Reviewed on 28 Aug, 2026
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.
What to do in Chelmsford
Battle of Lexington and Concord Self-Guided Driving Audio Tour
S$19
per traveller
94% of travellers recommend
Lexington, Massachusetts - Liberty Ride Trolley Tour
S$52
per adult
90% of travellers recommend
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
S$65
per adult
Frequently asked questions
How much does a Chelmsford holiday package cost?
Offering excellent value package deals from S$1,924 on Expedia, you'll be pleasantly surprised at how much a holiday to Chelmsford costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Chelmsford?
January, February and November are great times to look for cheap Chelmsford holiday packages. Opting to travel in less busy months means you can usually find reduced prices on flights and hotels.
How many days is enough for Chelmsford?
Usually, a handful of days is enough to check out the top attractions during your Chelmsford holiday. But if you want to have some time to kick back or take day trips, think about extending your trip.
How to find the best Chelmsford package deals?
Begin your search for a Chelmsford package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Chelmsford package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chelmsford escape underway.
Is it cheaper to book a Chelmsford holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging stays and flights separately. Better still, you can personalise your Chelmsford trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chelmsford?
If you're considering a spontaneous Chelmsford getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Chelmsford?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chelmsford.
- Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Chelmsford. Then, select a property that matches your budget, whether that's a low-cost stay or a high-end getaway.
- Decide how many days away: Start by making a list of all the activities and attractions you'd like to get to in Chelmsford. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, lock in the ideal Chelmsford holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
