Chelmsford Holidays

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Top Flight + Hotel Deals in Chelmsford

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 7 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Staff was extremely nice and accommodating. From the front desk, housekeeping, rooftop servers; everyone was nice and helpful. Rooms were small but had everything we needed. Clean and modern. The location was great too. Seaport is a charming part of Boston. Loved it :)

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
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per person
10 Sept - 13 Sept
found 7 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
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per person
10 Sept - 13 Sept
found 7 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 7 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great stay. Rooftop pool and easy access to multiple T stops for walking. Only complaint was the shower had water underneath the tub and it inpacted our ability to shower before dinner. However maintenance quickly resolved the issue, although with only a short term fix.

Reviewed on 27 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 7 hours ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
Everything was fantastic, luxurious, loved it all

Reviewed on 27 Jul 2025

Top hotels in Chelmsford

The Arcadian Hotel

The Arcadian Hotel

3.5 out of 5
1200 Beacon St, Brookline, MA
Fully refundableReserve now, pay when you stay
The price is €172 per night from 30 Jul to 31 Jul
€172
30 Jul - 31 Jul
includes taxes & fees
8/10 Very Good! (3,246 reviews)
"Hotel is 3 mile from downtown, tram stop right outside hotel very easy commute 25mins"

Reviewed on 25 Jul 2025

The Arcadian Hotel
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive, Cambridge, MA
The price is €153 per night from 10 Aug to 11 Aug
€153
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,038 reviews)
"It is next to MIT. However, there are no restaurants or shops within short walking distance of the hotel. Otherwise, the hotel is fine, but on the older side. There's a huge parking structure next to the hotel, which as great. The restaurant staff were great."

Reviewed on 27 Jul 2025

Hyatt Regency Boston/Cambridge
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway, Everett, MA
Fully refundableReserve now, pay when you stay
The price is €292 per night from 25 Aug to 26 Aug
€292
25 Aug - 26 Aug
includes taxes & fees
9.6/10 Exceptional! (3,145 reviews)
"Super nice property. Loved the shuttle and boat transportation. The staff was incredible. The rooms are fantastic."

Reviewed on 25 Jul 2025

Encore Boston Harbor
See all 1,484 properties in Chelmsford
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.

Frequently asked questions

How much does a Chelmsford holiday package cost?
Offering excellent value package deals from €546 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.