Rutland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Rutland Vacation

When the travel bug bites, book a vacation package to Rutland. Get ready to experience walking trails, camping, nature, and more in this vibrant destination. Can't decide what should come first? Oakham is one of the most well-known cities to explore during a trip to Rutland. Expedia is your one-stop shop for planning your Rutland vacation. From flights and accommodations, to rental cars and activities, we're here to help you create a travel experience like no other.

Top Rutland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Urban Hotel Grantham

Urban Hotel Grantham

2 out of 5
Price was CA $1,307, price is now CA $1,192 per person
CA $1,192
per person
Jun 10 - Jun 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
8/10 Very Good! (155 reviews)
Staff very friendly and helpful

Reviewed on Apr 30, 2026

The Collyweston Slater

The Collyweston Slater

3.5 out of 5
Price was CA $2,102, price is now CA $1,755 per person
CA $1,755
per person
Jun 10 - Jun 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
8.6/10 Excellent! (22 reviews)
Friendly, helpful. Fantastic room. Excellent food. Really super. Thank You

Reviewed on Jun 21, 2025

Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
Price was CA $1,407, price is now CA $1,218 per person
CA $1,218
per person
Jun 10 - Jun 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
8/10 Very Good! (789 reviews)
Very decent for the price!

Reviewed on Apr 30, 2026

The Three Swans Hotel, Market Harborough, Leicestershire

The Three Swans Hotel, Market Harborough, Leicestershire

4 out of 5
Price was CA $1,965, price is now CA $1,712 per person
CA $1,712
per person
Jun 10 - Jun 20
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
8.8/10 Excellent! (891 reviews)
Breakfast was delicious

Reviewed on Apr 13, 2026

Rutland Hotel Deals

Rutland Hall Hotel & Spa

Rutland Hall Hotel & Spa

4 out of 5
North Oakham Oakham England
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from May 11 to May 12
CA $207
CA $248 total
May 11 - May 12
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
The “hotel” is really a series of separate buildings spread out across a large site. There is no central location to meet for drinks/ coffee. The only restaurant is at the top of a hill (accessed by steep stairways/roads ). There appeared to be some golf buggies but it was not clear how these could ...

Reviewed on May 4, 2026

Rutland Hall Hotel & Spa
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 11 to May 12
CA $231
CA $278 total
May 11 - May 12
includes taxes & fees
9/10 Wonderful! (690 reviews)
Nice place with a great steak dinner

Reviewed on May 6, 2026

The Barnsdale, Rutland
Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
The price is CA $68 per night from May 10 to May 11
CA $68
CA $81 total
May 10 - May 11
includes taxes & fees
8/10 Very Good! (792 reviews)
We booked a room for 2 adults and 2 children. We have previously stayed at the hotel a few years ago and had no problems. Yet this time when we went in the sofa bed was not set up. We spoke to the lady in reception who came back to the room with covers and we were told it was normal that guests set ...

Reviewed on May 5, 2026

Redwings Lodge Uppingham
See all 1,867 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 Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Rutland vacation package cost?
Starting from just CA $1,192, a package is your passport to cheap travel. Put together your Rutland escape by picking from our great range of hotels, airfares and rental cars.
How do I get a cheap travel package to Rutland?
You'll save tons of cash if you combine your flights, hotels and car rentals into a Rutland vacation package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer over 550 airlines and 1,000,000 hotels throughout the world, so you'll always have plenty of variety to choose from. Want to save even more? Add some popular activities to your package deal and unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
What are the top hotels in Rutland?
When it comes to properties in Oakham, Rutland Hall Hotel and The Wisteria Hotel are two fantastic options. If you're visiting Stamford, Delta Hotels by Marriott Peterborough and Crown Hotel Stamford will make you feel right at home.
How far in advance should I book my Rutland vacation?
It's difficult to pick the perfect time for airfares, but we generally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to a year in advance. If you're booking last minute, don't fret. Discounted prices occasionally appear just weeks before departure dates.
What does an Expedia Rutland travel package include?
Hotels, flights and rental cars, or any combination of them — it's your pick! Whether you're headed to Rutland with the entire family or traveling by yourself, there's a bundle to match every style and budget. Once you've made your booking, why not add on some tours or activities?
What should I know before booking a Rutland travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've made your booking, you can add on things like activities or tours. Your next awesome vacation is only a few clicks away.
Can I choose my airline with a Rutland Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you certainly can. Just pick your preferred carrier and craft your ideal Rutland getaway.
If I'm not able to travel, can I cancel my Rutland vacation package?
Your situation can change unexpectedly, so yes, you can. You may be able to cancel and rebook your Rutland vacation package for free if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, airline or hotel may charge a fee. Want more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.