Chesterfield Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Chesterfield

Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is S$156 per night from 3 Dec to 4 Dec
S$156
includes taxes & fees
3 Dec - 4 Dec
6.6/10 (1,000 reviews)
"The staff are nice"

Reviewed on 12 Nov,2024

Colonial Motel And Spa
Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is S$144 per night from 22 Dec to 23 Dec
S$144
includes taxes & fees
22 Dec - 23 Dec
8.2/10 Very Good! (1,001 reviews)
Rested
"Easiet and nicest place ive stayed in a while"

Reviewed on 16 Nov,2024

Hampton Inn Brattleboro
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 1 Dec to 2 Dec
S$108
includes taxes & fees
1 Dec - 2 Dec
8/10 Very Good! (1,000 reviews)
"The housekeeping services were excellent and the staff was friendly The facility is a bit old but incredibly clean"

Reviewed on 18 Nov,2024

The Covered Bridge Inn
See all 481 properties in Chesterfield
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 Chesterfield holiday package cost?
Our Chesterfield packages, which start from just , are the perfect way to save precious money. Choose your favourite hotels, flights and more to create a custom-built escape.
How do I get a cheap travel package to Chesterfield?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we’ve got them all. Choose the combination that best suits you and see your savings pile up. We know a package deal is never one-size-fits-all. That’s why we offer more than 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Chesterfield holiday.
Where should I stay in Chesterfield?
With interesting attractions like Spofford Lake and Madame Sherri Forest in this area, see if you can find a hotel near either one. Asbury United Methodist Church is another sight in Chesterfield that lures the crowds.
How far in advance should I book my Chesterfield holiday?
It depends on the air carrier, but you can generally look up international airfares on Expedia nearly a year in advance. While it’s generally recommended to book ahead of time, lucky travellers occasionally find a cheaper ticket just weeks prior to departure dates.
What does an Expedia Chesterfield travel package include?
With Expedia, you can choose any combination of flights, car rentals and hotels to create your perfect Chesterfield travel package. Once you’ve made your booking, you can add on all the fun stuff like sightseeing tours and activities. Remember — the more you bundle, the greater the savings!
What should I know before booking a Chesterfield travel package?
Whether it’s relaxation or adventure you’re after, a Chesterfield holiday package lets you organise your escape your way. Plus, you’ll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Chesterfield Expedia holiday package?
Expedia offers access to more than 550 airline partners worldwide, so you certainly can. Just pick the airline you want and craft your ideal Chesterfield trip.
If I'm not able to travel, can I cancel my Chesterfield holiday package?
We get that the universe can throw the odd curveball. If you’ve booked a Chesterfield holiday package and have to amend or cancel it, we’re here to help. It’s always worth looking up our Customer Service Portal first for information. But generally, if you’ve taken out your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it’s more than 24 hours, your airline, hotel or car rental company may impose a fee.

* 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.