Rutland Vacations from $284

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The Latest Rutland vacation packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $644, price is now $284 per person
$284
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (3,229 reviews)
Room was clean, comfortable, and quiet. Staff was very friendly and even let us check in early. Would stay there again.

Reviewed on Nov 18, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $761, price is now $312 per person
$312
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (1,367 reviews)
from the staff to the clean rooms and all the fun things in the resort... WAS GREAT!!!!

Reviewed on Nov 18, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,818, price is now $846 per person
$846
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $751, price is now $353 per person
$353
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (2,232 reviews)
Couldn't check untill 4pm. One small bottle of soap for 3 people and it was never replaced.

Reviewed on Nov 17, 2025

Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Save 100% on your flight
Price was $731, price is now $360 per person
$360
per person
Jan 28 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.2/10 Exceptional! (1,549 reviews)
Overall, the service was excellent. Our stay at the hotel was a fantastic experience.

Reviewed on Nov 18, 2025

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Rutland Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$124 nightly
The price is $133 total per night from Dec 2 to Dec 3
$133 total
Dec 2 - Dec 3
Total with taxes and fees
9/10 Wonderful! (1,248 reviews)
Nice staff

Reviewed on Nov 10, 2025

The Waterfront Inn
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $181 total per night from Nov 30 to Dec 1
$181 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (1,048 reviews)
Very nice new hotel. Staff was excellent!

Reviewed on Nov 11, 2025

Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44 Wildwood FL
Fully refundable
$103 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
My husband and I stayed at the Holiday Inn Express during a little mini vacation, and it was a wonderful experience from start to finish. The staff was incredibly friendly and welcoming. Our room was updated, spotless, and very quiet, which made for a relaxing stay. The breakfast offered a large ...

Reviewed on Nov 18, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,290 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.

Find the Best Rutland Vacation Packages

Rutland Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Rutland vacation package cost?
You'll find cheap prices from $284 on Expedia for your Rutland getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Rutland costs.
What are the cheapest months to go to Rutland?
June, July and October are great times to search for cheap Rutland vacation packages. Traveling in less busy periods means you can generally find reduced prices on hotels and flights.
How many days is enough for Rutland?
Typically, a handful of days is enough to explore the main attractions during your Rutland vacation. However, if you want to have more time to relax or take day tours, consider extending your itinerary.
How to find the best Rutland package deals?
Use Expedia's handy filters to help you find some terrific Rutland package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Rutland package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Rutland vacation as a package?
You can enjoy significant savings on your next Rutland retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Rutland?
Secure amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Rutland trip.
Does Expedia offer Book Now, Pay Later Rutland vacation packages?
Set off on your perfect escape to Rutland with our Book Now, Pay Later vacations. No need to save up or wait for payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's a breeze to stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.