Rutland Holidays

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Your Rutland Holiday

Planning your next big escape is easy with a Rutland holiday package. The neighbourhood of Webster Square, which is good for cycling, makes an ideal starting point to uncover the treasures of this lively city. You'll want to do some exploring during your trip to Rutland. Swing by famous attractions like Moore State Park, Rutland State Park and Saint Josephs Abbey. Whoever you're travelling with and whatever you plan to spend, your dream Rutland holiday is only clicks away with Expedia.

Rutland Holiday

Rutland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
2,100
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Wachusett Mountain Ski Area, The Hanover Theatre for the Performing Arts and Worcester Art Museum

Our pick of the best Rutland Hotel Deals

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$153 per night from 26 Aug to 27 Aug
AU$153
26 Aug - 27 Aug
includes taxes & fees
8.8/10 Excellent! (1,466 reviews)
"Front desk staff were very friendly and helpful. Beautiful property. Wonderful bakery. Very comfortable and convenient in our travels. Have stayed here several times."

Reviewed on 17 Aug. 2025

Publick House Historic Inn and Country Motor Lodge
Courtyard by Marriott Boston Marlborough

Courtyard by Marriott Boston Marlborough

3 out of 5
75 Felton St, Marlborough, MA
The price is AU$218 per night from 24 Aug to 25 Aug
AU$218
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Property is really nice and rooms were really clean . Staff was amazing and love the fact that there is a bar/ restaurant down stairs if your in the mood for a drink and a bite"

Reviewed on 16 Aug. 2025

Courtyard by Marriott Boston Marlborough
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 AU$205 per night from 28 Aug to 29 Aug
AU$205
28 Aug - 29 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"In general, everything was fine. But breakfast, although it has options, is a little expensive for what they offer. Scrambled eggs and potatoes don't taste the best and French toasts are also a bit regular. The bacon was good but in general it looks like airplane food, so the breakfast is overpriced. ..."

Reviewed on 17 Aug. 2025

DoubleTree by Hilton Hotel Boston - Westborough
See all 313 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.
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 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.