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.
Stylish 1BR Flat Next to Hockley

Stylish 1BR Flat Next to Hockley

3 out of 5
Nottingham City Centre
Price was CA $1,736, price is now CA $1,466 per person
CA $1,466
per person
Aug 1 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
6.8/10 (3 reviews)
Ringwood

Ringwood

2 out of 5
Price was CA $2,052, price is now CA $1,698 per person
CA $1,698
per person
Aug 1 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
No reviews
Comfy 3BR Flat on Quiet Street

Comfy 3BR Flat on Quiet Street

2 out of 5
Price was CA $1,990, price is now CA $1,654 per person
CA $1,654
per person
Aug 1 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
No reviews
Spacious & Luxury 2BR Flat in Calverton

Spacious & Luxury 2BR Flat in Calverton

2 out of 5
Price was CA $1,925, price is now CA $1,655 per person
CA $1,655
per person
Aug 1 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
No reviews
Bestwood Lodge

Bestwood Lodge

3 out of 5
Price was CA $1,804, price is now CA $1,591 per person
CA $1,591
per person
Aug 1 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to East Midlands (EMA)
7.6/10 Good! (406 reviews)
Atmospheric rooms and bar. Clean rooms and comfortable bed. Bathroom was unheated and cold. But if this was resolved I can recommend this hotel as a great base to explore Nottingham.

Reviewed on Dec 12, 2025

Rutland Hotel Deals

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 $226 per night from Jul 8 to Jul 9
CA $226
CA $271 total
Jul 8 - Jul 9
includes taxes & fees
9/10 Wonderful! (710 reviews)
"Staff were amazing my first room number 9 smelt of damp and they quickly moved me, food amazing, spa amazing will definitely be back x"

Reviewed on Jun 19, 2026

The Barnsdale, Rutland
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 $233 per night from Jun 28 to Jun 29
CA $233
CA $279 total
Jun 28 - Jun 29
includes taxes & fees
Rutland Hall Hotel & Spa
Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
The price is CA $68 per night from Jun 28 to Jun 29
CA $68
CA $82 total
Jun 28 - Jun 29
includes taxes & fees
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

Redwings Lodge Uppingham
See all 1,897 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
Beach Vacations
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Frequently asked questions

How much does a Rutland vacation package cost?
Starting from just CA $1,466, 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.