Rutland Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Rutland

DoubleTree by Hilton Hotel Boston - Westborough
DoubleTree by Hilton Hotel Boston - Westborough
4 out of 5
5400 Computer Dr, Westborough, MA
Fully refundableReserve now, pay when you stay
The price is S$160 per night from 1 Jul to 2 Jul
S$160
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"The room was small, but clean. The overall facility was clean and the staff was friendly."

Reviewed on 18 Jun, 2025

DoubleTree by Hilton Hotel Boston - Westborough
Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$167 per night from 6 Jul to 7 Jul
S$167
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,190 reviews)
"Loved it. Will return soon and often!"

Reviewed on 17 Jun, 2025

Wellsworth Hotel
Courtyard by Marriott Boston Marlborough
Courtyard by Marriott Boston Marlborough
3 out of 5
75 Felton St, Marlborough, MA
Fully refundableReserve now, pay when you stay
The price is S$194 per night from 29 Jun to 30 Jun
S$194
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Welcoming staff, easy check in/ out, dining options, quiet/safe, comfortable bed and pillows, updated bathroom."

Reviewed on 15 Jun, 2025

Courtyard by Marriott Boston Marlborough
See all 306 properties in Rutland
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 Rutland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Rutland costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Rutland?
To score cheap Rutland holiday packages, plan your getaway outside of busy periods like public holidays and major festivals. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Rutland?
With a well-planned schedule, you can easily visit the top Rutland sights in a few days. But if you'd like to discover hidden gems or go on day tours, think about booking your Rutland holiday for longer.
How to find the best Rutland package deals?
Landing a cheap Rutland package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Rutland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Rutland holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component separately. And you'll still enjoy the freedom to create a customised Rutland holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Rutland?
If you've got your Rutland travel dates finalized, book as early as you can to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Rutland?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Rutland.
  2. Set your budget: Factor in expenses like flights, meals and transportation when calculating how much to put aside for your trip to Rutland. Then, select a hotel that fits your budget, whether that's a low-cost stay or a swankier retreat.
  3. Decide your trip length: Think about how much time you want to spend exploring Rutland. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Rutland holiday package.

* 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.