Orwell Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 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

Orwell Holiday

Our pick of the best Orwell Hotel Deals

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is NZ$295 per night from 2 July to 3 July
NZ$295
2 July - 3 July
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Wonderful place to stay in quaint Middlebury. Historic inn and very nice, clean rooms. Love the rocking chairs on the front porch."

Reviewed on 18 Jun. 2025

Middlebury Inn
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is NZ$230 per night from 29 June to 30 June
NZ$230
29 June - 30 June
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"Great service"

Reviewed on 22 Jun. 2025

Comfort Inn Rutland - Killington
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
3 out of 5
87 Silver Bay Rd, Silver Bay, NY
Fully refundableReserve now, pay when you stay
The price is NZ$165 per night from 25 June to 26 June
NZ$165
25 June - 26 June
includes taxes & fees
8.4/10 Very Good! (90 reviews)
"Nice , serene place with a lot of attractions within the property . I really liked the place and my family as well"

Reviewed on 19 May 2025

Silver Bay YMCA Inn and Conference Center
See all 550 properties in Orwell
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 an Orwell holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Orwell costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Orwell?
January, February and March are great times to search for cheap Orwell holiday packages. Travelling in less busy periods means you can usually find lower prices on accommodation and flights.
How many days is enough for Orwell?
The ideal length for your Orwell holiday depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to visit all the main attractions and explore some hidden spots along the way.
How to find the best Orwell package deals?
Start your search for an Orwell package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Orwell package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Orwell adventure underway.
Is it cheaper to book an Orwell holiday as a package?
You can enjoy significant savings on your next Orwell break by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Orwell?
If you're considering a spontaneous Orwell getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Orwell?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Orwell.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to save for your trip to Orwell. Then, choose a hotel that fits your budget, whether that's an economical option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you'd like to experience in Orwell. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find an Orwell holiday package that brings all your bookings together.

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