$532 Cheap flights to Rutland

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Cheap flights to Rutland from $532 One Way, $1,209 Round Trip

$1,209 return flights and $532 one-way flights to Rutland were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,209 Roundtrip, found 2 days ago
$1,209
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,209 found 2 days ago
Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,219 Roundtrip, found 2 days ago
$1,219
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,219 found 2 days ago
Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,222 Roundtrip, found 2 days ago
$1,222
Roundtrip
found 2 days ago
Select Iberia flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,222 found 2 days ago
Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,223 Roundtrip, found 2 days ago
$1,223
Roundtrip
found 2 days ago
Select Iberia flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,223 found 2 days ago
Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,226 Roundtrip, found 2 days ago
$1,226
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,226 found 2 days ago
Tue, Oct 20 - Wed, Oct 28
JFK
New York
EMA
East Midlands
$1,233 Roundtrip, found 2 days ago
$1,233
Roundtrip
found 2 days ago
Select Iberia flight, departing Tue, Oct 20 from New York to East Midlands, returning Wed, Oct 28, priced at $1,233 found 2 days ago
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Deals For This Weekend's Flights

Find The Perfect Hotel For After Your Flight

Score Epic Rutland Accommodation Deals

Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
$49 nightly
The price is $59 total per night from Jul 5 to Jul 6
$59 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (801 reviews)
"Lovely warm reception when I arrived, which was nice and the staff were very helpful throughout my stay. The outside area around the hotel was very neglected, which didn’t give a great impression but the rooms were very clean, if a little tired and in need of some re-furnishing. For the price paid, ..."

Reviewed on Jun 13, 2026

Opens in a new windowRedwings Lodge Uppingham
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
$137 nightly
The price is $165 total per night from Jun 21 to Jun 22
$165 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this spa hotel in Oakham. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (709 reviews)
"We had a fantastic stay at The Barnsdale, such a beautiful, relaxing and picturesque venue. We enjoyed use of the spa, which is beautifully done, small and intimate. Evening meal in the Brasserie was delicious with fabulous service and breakfast was just as delicious, with lots of choice and was ..."

Reviewed on Jun 14, 2026

Opens in a new windowThe Barnsdale, Rutland
The Wisteria Hotel

The Wisteria Hotel

3 out of 5
Catmose Street Oakham England
$112 nightly
The price is $134 total per night from Jul 13 to Jul 14
$134 total
Jul 13 - Jul 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakham. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (371 reviews)
"Comfortable rooms. Tasty meals. Very helpful staff. Parking is very tight and can get full quickly. Alternative overnight parking available in the long term museum car park next door. Free parking between 18.00 and 08.00"

Reviewed on Jun 8, 2026

Opens in a new windowThe Wisteria Hotel
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Brook Whipper-In Hotel

Brook Whipper-In Hotel

3 out of 5
Market Square Oakham England
Book a stay at this business-friendly hotel in Oakham. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Oakham Castle and Rutland ...
7.4/10 Good! (174 reviews)
Fishing Trip
"Good hotel just stayed one night food in the restaurant was good and better than the usual pub fayre Good value, only one fault was the shower in the room wasn't very good, poor water pressure and not very controllable either red hot or cold."

Reviewed on Sep 18, 2023

Get rates
Opens in a new windowBrook Whipper-In Hotel
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.

Score Epic Rutland Accommodation Deals

Rutland Hall Hotel & Spa

Rutland Hall Hotel & Spa

4 out of 5
North Oakham Oakham England
$150 nightly
The price is $180 total per night from Jul 5 to Jul 6
$180 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this spa hotel in Oakham. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Opens in a new windowRutland Hall Hotel & Spa
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
$137 nightly
The price is $165 total per night from Jun 21 to Jun 22
$165 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this spa hotel in Oakham. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (709 reviews)
"We had a fantastic stay at The Barnsdale, such a beautiful, relaxing and picturesque venue. We enjoyed use of the spa, which is beautifully done, small and intimate. Evening meal in the Brasserie was delicious with fabulous service and breakfast was just as delicious, with lots of choice and was ..."

Reviewed on Jun 14, 2026

Opens in a new windowThe Barnsdale, Rutland
Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
$49 nightly
The price is $59 total per night from Jul 5 to Jul 6
$59 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (801 reviews)
"Lovely warm reception when I arrived, which was nice and the staff were very helpful throughout my stay. The outside area around the hotel was very neglected, which didn’t give a great impression but the rooms were very clean, if a little tired and in need of some re-furnishing. For the price paid, ..."

Reviewed on Jun 13, 2026

Opens in a new windowRedwings Lodge Uppingham
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Burleigh Court Hotel

Burleigh Court Hotel

4 out of 5
Loughborough University Loughborough England
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $106 total per night from Jul 5 to Jul 6
$106 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this spa hotel in Loughborough. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,002 reviews)
"Good location for events and the airport. Good quality food, affordable spa on site and modern well designed on site bar and restaurant. Lovely helpful staff and clean rooms x"

Reviewed on Jun 15, 2026

Opens in a new windowBurleigh Court Hotel
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.

Family Friendly Hotels in Rutland

Rutland Hall Hotel & Spa

Rutland Hall Hotel & Spa

4 out of 5
North Oakham Oakham England
$150 nightly
The price is $180 total per night from Jul 5 to Jul 6
$180 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this spa hotel in Oakham. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
Opens in a new windowRutland Hall Hotel & Spa
The White Lion Inn

The White Lion Inn

3 out of 5
38 Main Street Oakham England
$113 nightly
The price is $136 total per night from Jun 28 to Jun 29
$136 total
Jun 28 - Jun 29
Total with taxes and fees
Stay at this inn in Oakham. Enjoy free parking, breakfast (surcharge), and a business center. Popular attractions Stapleford Park Golf Course and Oakham Castle ...
9.6/10 Exceptional! (419 reviews)
"Always like staying here. Not sure if the breakfast menu has been revised, but I did appreciate the poached egg and salmon"

Reviewed on Jun 15, 2026

Opens in a new windowThe White Lion Inn
Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
$49 nightly
The price is $59 total per night from Jul 5 to Jul 6
$59 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Oakham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (801 reviews)
"Lovely warm reception when I arrived, which was nice and the staff were very helpful throughout my stay. The outside area around the hotel was very neglected, which didn’t give a great impression but the rooms were very clean, if a little tired and in need of some re-furnishing. For the price paid, ..."

Reviewed on Jun 13, 2026

Opens in a new windowRedwings Lodge Uppingham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
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The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
$137 nightly
The price is $165 total per night from Jun 21 to Jun 22
$165 total
Jun 21 - Jun 22
Total with taxes and fees
Book a stay at this spa hotel in Oakham. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (709 reviews)
"We had a fantastic stay at The Barnsdale, such a beautiful, relaxing and picturesque venue. We enjoyed use of the spa, which is beautifully done, small and intimate. Evening meal in the Brasserie was delicious with fabulous service and breakfast was just as delicious, with lots of choice and was ..."

Reviewed on Jun 14, 2026

Opens in a new windowThe Barnsdale, 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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Rutland?
Lock in an airfare with one of the 12 airlines that jet into East Midlands Airport (EMA) and come prepared for new adventures. This airport is the jumping-off point for exploring Rutland. When it's time to check off this region, these quality carriers will take you there:

  • Ryanair - 208 flights to Rutland per month
  • Jet2 - 120 flights to Rutland per month
  • Flybe - 30 flights to Rutland per month

What is the best airport to fly to in Rutland?
There's one main entry point for this area — East Midlands Airport (EMA). Book your airfares for this popular gateway and explore all that Rutland has to offer.
How much is a flight to Rutland?
The cost for a round-trip flight to Rutland this week ranged between $1,209 and $1,233. If you were traveling one-way out of New York (JFK), you could have scored tickets from as low as $532.
How to book the cheapest flight to Rutland?
Scoring cheap flights to Rutland is as simple as booking with Orbitz. But if you'd like to make sure you're grabbing the best flight deals around, here are some suggestions to keep in mind:

  • Consider nearby airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list the available options.
  • If your travel plans aren't cast in stone, click on the 'Show flexible dates' link to compare flight deals for a variety of departure dates. You may find an amazing fare.
  • Select 'Show options' to fine tune your search results. You can pick your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you want to fly in the morning, afternoon or evening.
  • Once you've worked out your travel dates, lock in your flight. Airfares generally rise as the departure date gets closer.
  • Make even more savings on your getaway by bundling your flights, hotels and car rentals into an Orbitz package deal. Your travel budget will thank you for it.
  • If practical, avoid flying in high seasons. Airfares usually surge during school breaks, summer and other vacation periods like Thanksgiving and Christmas.

What is the best time to book a flight to Rutland?
Pick up a bargain and book your tickets to Rutland in January. If you've missed this month, you're still in luck. February and August often have low airfares available. Just be careful you don't sleep on a sale though — cheap flights appear and vanish in the click of a mouse!
What day of the week is the cheapest to book a flight to Rutland?
When it comes to cheap flights to Rutland, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A fabulous flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Rutland?
Look into flying early in the week to nab cheap flights to Rutland. Orbitz data from 2020 suggests Monday is typically the most inexpensive day to start your trip, followed by Tuesday. Saturday was found to have the highest airfares. Presumably, this is because most travelers choose to start their break on a weekend.
What is the cheapest month to fly to Rutland?
To pick up cheap flights to Rutland, you should pack your bags and travel in August. Orbitz data shows that this is generally an excellent month to save serious money on your fare. If you're thinking of flying to Rutland during June, it's worth remembering that this is the most expensive time of year to travel.
Which airlines allow free cancellation?
Life changes, and your ticket should be able to as well. That's why Orbitz makes it a cinch to search for airlines with free cancellation and no change fees. Just enter your departure and arrival points and then select "Filter by flexible change policies." That's what we call peace of mind!
What do I need for the flight to Rutland?
It's wise to be ready for anything when embarking on a trip. Keep in mind the following for a smooth flight:

  • Nothing is more important than having your travel documents. Which to bring and how many depend on whether you're flying international or domestic. It's best to check with your airline. In both cases, you'll need to present photo identification.
  • Have some extra entertainment for your long trip to Rutland. When you're done watching movies, give your eyes a much-needed break from all that screen time and listen to an audio book.
  • Cabin temperatures can get real chilly. Carry a sweater even if you're heading off during the peak of summer.

How many direct flights are there to Rutland?
Right now, there are 95 direct flights each month to Rutland. When it comes to airlines that will fly you there, you have plenty of options. Ryanair, Jet2 and TUI Airways are some of the most sought-after. Flybe, Blue Islands and Aurigny Air Services are some other dependable carriers that offer nonstop services.
How do I get cheap first-class/business deals to Rutland?
There are ways of booking first or business-class tickets to Rutland that won't burn through your budget. Bag a seat in the pointy end of the plane for less with these handy tips:

  • Flexibility is key. By being open to a few travel dates, you'll have more chances of finding a deal on business or first-class airfares.
  • Budget airlines offer business-class seats at a fraction of the normal price. Skip the full-service carriers and check out these cheaper options.
  • Make the most of your airline's loyalty program and use points to upgrade your seat. You can also bid for an upgrade in an online auction if available.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.