Rutland Vacations & Trips from $795

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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.

The Latest Rutland Vacation Packages

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

Silk Hotel

2 out of 5
Price was $887, price is now $795 per person
$795
per person
Sep 18 - Sep 22
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to East Midlands (EMA)
No reviews

OYO Diamond Apartments Skegness

OYO Diamond Apartments Skegness

2.5 out of 5
Price was $1,181, price is now $1,025 per person
$1,025
per person
Aug 24 - Aug 29
found 15 hours ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
5.6/10 (119 reviews)
Close to the front and shops.

Reviewed on Jul 4, 2026

Quorn Grange Hotel

Quorn Grange Hotel

3 out of 5
Price was $939, price is now $826 per person
$826
per person
Sep 18 - Sep 22
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to East Midlands (EMA)
8.2/10 Very Good! (421 reviews)
We travelled very far and when we arrived it was early for check-in however, although check-in was at 3pm we were told our room was not ready still and had to wait. The shower in the room wasn't working which no one told us about when we tried to change rooms this was not possible and we were told there is a bath to use this. The bath had no shower attachment making it very difficult to use and with 4 of us sharing this made washing very long. We were very disappointed that despite all these issues there was no gesture of goodwill.

Reviewed on Jul 8, 2026

Holywell Guest House

Holywell Guest House

4 out of 5
Price was $1,108, price is now $977 per person
$977
per person
Sep 18 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to East Midlands (EMA)
10/10 Exceptional! (78 reviews)
We booked a family room as we had a family party nearby. The room was beautiful and clean, the owners were welcoming and friendly and it was all made better with a lovely breakfast to set us up for a long journey home. Would definitely recommend 5*

Reviewed on Jul 6, 2026

The Old Pheasant Hotel

The Old Pheasant Hotel

3 out of 5
Price was $937, price is now $829 per person
$829
per person
Sep 18 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
New York (NYC) to East Midlands (EMA)
9.2/10 Wonderful! (122 reviews)
A great place and easy to find. Staff were friendly and helpful. Nice breakfast.

Reviewed on Jul 10, 2026

Find the Best Rutland Vacation Packages

Rutland Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
East Midlands Airport (EMA)

Rutland Hotel Deals

Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
$53 nightly
The price is $63 total per night from Aug 2 to Aug 3
$63 total
Aug 2 - Aug 3
Total with taxes and fees
8/10 Very Good! (807 reviews)
"Good value accommodation When the cafe next door is reopened it would be ideal"

Reviewed on Jul 9, 2026

Redwings Lodge Uppingham
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $177 total per night from Aug 4 to Aug 5
$177 total
Aug 4 - Aug 5
Total with taxes and fees
9/10 Wonderful! (714 reviews)
"The Barnsdale hotel is in a lovely and convenient setting with ample parking. The Sydnet spa is great and the pool was wonderful for an afternoon cool down. Plus super cute Highland cows! Breakfast and dinner is wonderful in the beautiful courtyard. The Barnsdale is an old building which means the ..."

Reviewed on Jul 10, 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
$150 nightly
The price is $180 total per night from Jul 27 to Jul 28
$180 total
Jul 27 - Jul 28
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Overall the property and grounds are lovely, although I was there for a wedding so didn't have much time to explore and enjoy them properly. I also didn't use the spa so can't comment on that. The weekend was hot (but not heatwave) and the rooms were incredibly hot. There is no AC in the bedrooms ..."

Reviewed on Jul 3, 2026

Rutland Hall Hotel & Spa
See all 1,935 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.
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Frequently asked questions

How much does a Rutland vacation package cost?
Starting from just $795, a package is your passport to low-priced travel. Create your own Rutland getaway by picking from our wide range of hotels, flights and rental cars.
How do I get a cheap travel package to Rutland?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all covered. Select a combination that best fits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties globally, which lets you customize your Rutland adventure.
What are the top hotels in Rutland?
For properties in Oakham with comfy beds and friendly service, you can't beat Brook Whipper-In Hotel and Old White Hart. If you're visiting Stamford as well, you can look forward to a great night's sleep at Holiday Inn Peterborough West, an IHG Hotel or Delta Hotels by Marriott Peterborough.
How far in advance should I book my Rutland vacation?
Reserving your seat early with Expedia means one less thing to worry about. Most carriers display prices up to 12 months prior to departure dates. This is generally the cheapest time to book. If circumstances have left you booking late, low prices to Rutland sometimes occur just a few weeks before departure.
What does an Expedia Rutland travel package include?
Hotels, flights and rental cars — we have them well covered. With Expedia, you can create your Rutland travel package the way you want. All you have to do is work out exactly what you need. Once you've made your booking, you can add extras like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Rutland travel package?
A package can be easier on the wallet than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever sort of vacation you're planning, there's sure to be a package that best suits your budget.
Can I choose my airline with a Rutland Expedia vacation package?
With a vacation package, you're in charge. Whether you'd like to fly to Rutland in first class or coach, simply select from the available airline options. Expedia has access to more than 550 partner airlines throughout the world.
Does Expedia offer Book Now, Pay Later Rutland vacation packages?
If your need to travel has arisen unexpectedly, Expedia can help take the financial strain off your shoulders. Working with online lender Affirm, we provide a Book Now, Pay Later option for all package bookings. It's easy to set up a payment plan for your vacation that works for you.
If I'm not able to travel, can I cancel my Rutland vacation package?
Yes, you can. We get that life happens, so we're happy to help if you need to make changes to your Rutland vacation package. It may be possible to amend or cancel your itinerary at no cost if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Look up our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Stay near popular Rutland attractions

A historic building on an island in a body of water, with a seagull flying overhead.
Photo by Tony Hicks
Open Photo by Tony Hicks

Rutland Water Nature Reserve

9.2/10 (240 reviews)
Commune with nature and explore the great outdoors at Rutland Water Nature Reserve during your travels in Oakham. Check out the lively bars or top-notch restaurants in this relaxing area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.