Rutland Trips (flight + hotel)

    deals illustration
    Better together
    Save up to P 3,118 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    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 P7,390 per night from Jul 2 to Jul 3
P7,390
P8,254 total
Jul 2 - Jul 3
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
Wonderful trip
"The stay was very nice, having access to washing machines was very helpful. And the pool was a life saver with the grandchildren."

Reviewed on Jun 26, 2025

DoubleTree by Hilton Hotel Boston - Westborough
Courtyard by Marriott Boston Marlborough
Courtyard by Marriott Boston Marlborough
3 out of 5
75 Felton St, Marlborough, MA
The price is P7,635 per night from Jul 3 to Jul 4
P7,635
P8,529 total
Jul 3 - Jul 4
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Great property!! Close to everything and very clean and modern"

Reviewed on Jun 26, 2025

Courtyard by Marriott Boston Marlborough
Wellsworth Hotel
Wellsworth Hotel
3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is P6,566 per night from Jul 2 to Jul 3
P6,566
P7,335 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,205 reviews)
"The hotel was very nice. Really impressed with facilities and a great rate."

Reviewed on Jun 25, 2025

Wellsworth Hotel
See all 309 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 vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 vacation 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," "Traveler 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 vacation as a package?
Expedia vacation 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 customized Rutland vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation 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 vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.