Chester Holidays from AU$2,846

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Your Chester Holiday

Book a Chester holiday package and get set to experience all this city has to offer. Think about staying in the neighbourhood of Downtown Manchester, which is great for cafes, history and bars and pubs. When it's time to get out and explore, be sure to include Zorvino Vineyards and Robert Frost Farm State Historic Site on the to-do list for your trip to Chester. A couple of clicks is all it takes to create your perfect Chester holiday on Expedia.

The Latest Chester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Beacon Hill Hotel

Beacon Hill Hotel

4 out of 5
Beacon Hill
Price was AU$4,000, price is now AU$2,846 per person
AU$2,846
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
8.8/10 Excellent! (235 reviews)
We enjoyed having the bistro on site.

Reviewed on 17 Jul. 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was AU$7,028, price is now AU$4,364 per person
AU$4,364
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
The staff were amazing, rooms were spotless and with wonderful amenities and special touches.

Reviewed on 22 Aug. 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was AU$6,212, price is now AU$3,972 per person
AU$3,972
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (147 reviews)
The Reffles Hotel is a fabulous place to stay. Hotel is amazing with a wonderful friendly staff.

Reviewed on 20 Aug. 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was AU$7,836, price is now AU$5,450 per person
AU$5,450
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
The Langham is a wonderful, luxurious family hotel. The staff were absolutely lovely and made a fuss over our young daughter which seems rare at hotels these days. The location of the hotel is also fantastic, as it's within walking distance to both the Boston Children’s Museum and the aquarium. The indoor pool was a fantastic added bonus that our family thoroughly enjoyed. We were so impressed with our experience that we will definitely be staying at The Langham again the next time we are in Boston.

Reviewed on 21 Aug. 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was AU$4,045, price is now AU$2,925 per person
AU$2,925
per person
12 Oct - 17 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Boston (BOS)
9.2/10 Wonderful! (1,108 reviews)
Heather was unbelievable in every way. Because of her past excellent service we returned!! She makes this hotel experience a true pleasure. Thank you Heather for your kind and gracious assistance.

Reviewed on 21 Aug. 2025

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Manchester-Boston Regional Airport (MHT)
Population
5,200
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Canobie Lake Park, Bear Brook State Park and Zorvino Vineyards

Our pick of the best Chester Hotel Deals

EVEN Hotels Manchester Airport by IHG

EVEN Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Fully refundable
The price is AU$177 per night from 31 Aug to 1 Sept
AU$177
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (884 reviews)
"It was great so good coming back"

Reviewed on 19 Aug. 2025

EVEN Hotels Manchester Airport by IHG
DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St., Manchester, NH
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 24 Aug to 25 Aug
AU$211
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"A great spot!"

Reviewed on 21 Aug. 2025

DoubleTree by Hilton Manchester Downtown
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd, Andover, MA
Fully refundableReserve now, pay when you stay
The price is AU$214 per night from 7 Sept to 8 Sept
AU$214
7 Sept - 8 Sept
includes taxes & fees
8/10 Very Good! (1,826 reviews)
"Good"

Reviewed on 16 Aug. 2025

La Quinta Inn & Suites by Wyndham Boston-Andover
See all 444 properties in Chester
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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Chester holiday package cost?
You'll find cheap prices from AU$2,846 on Expedia for your Chester escape. However, factors like the length of stay, hotel choice and season will determine how much your holiday to Chester costs.
What are the cheapest months to go to Chester?
If you're looking to score a cheap Chester holiday package, consider visiting in October, November and December. You'll typically find lower rates on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Chester?
The ideal duration of your Chester holiday depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the major sights and discover some hidden treasures along the way.
How to find the best Chester package deals?
Use Expedia's filter tool to help you find some great Chester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Chester package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Chester holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a customised Chester holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Chester?
If you've got your Chester holiday dates locked in, book as soon as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Chester?

  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the available activities will also help you decide when to escape to Chester.
  2. Set a budget: Consider expenses like flights, transportation and food when working out how much to save for your trip to Chester. Then, pick a hotel that matches your budget, whether that's an affordable stay or a deluxe getaway.
  3. Determine how many days away: Start by making a list of all the sights and activities you want to get to in Chester. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodation and airfare: Once you've nailed down your dates and duration, lock in the right Chester 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.