Middletown Springs Vacations from $291

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Your Middletown Springs Vacation

Our vacation packages to Middletown Springs give you the power to customize your own adventure. Tailor your journey to your interests and style and make every moment count in this wonderful city. Looking for some sightseeing tips for your trip to Middletown Springs? Lake Saint Catherine and Lake Saint Catherine State Park are two of the main attractions here. Don't delay exploring this city any longer. Your perfect Middletown Springs vacation is a few quick clicks away with Expedia.

The Latest Middletown Springs vacation packages

Price found within the past 48 hours. Click for updated prices.
The Vermont Inn

The Vermont Inn

3 out of 5
Price was $366, price is now $291 per person
$291
per person
Oct 31 - Nov 2
found 13 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9.2/10 Wonderful! (408 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $495, price is now $363 per person
$363
per person
Oct 31 - Nov 2
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.8/10 Excellent! (823 reviews)
Great little motel. Clean, well appointed, friendly staff and walkable location. We did not have good weather, but great fire pits and chairs near river.

Reviewed on Sep 25, 2025

The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $775, price is now $621 per person
$621
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Springfield (VSF)
7.8/10 Good! (1,003 reviews)
Clean, comfortable room. Modest continental breakfast.

Reviewed on Sep 26, 2025

The Vesper

The Vesper

3 out of 5
Price was $740, price is now $627 per person
$627
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
9.2/10 Wonderful! (32 reviews)
We enjoyed staying at the Vesper. We were on a front room which had continual road noise through the night. But it was kind of white noise and not really loud. The internet was terrible in the room, but it was very good when I went downstairs to the common area. Coffee and tea service and continental breakfast were very nice. And self check-in was very good.

Reviewed on Sep 2, 2025

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $592, price is now $510 per person
$510
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
9.4/10 Exceptional! (821 reviews)
Great location with beautiful views and activities on the lake.

Reviewed on Sep 23, 2025

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Middletown Springs Hotel Deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $145 total per night from Oct 20 to Oct 21
$145 total
Oct 20 - Oct 21
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
"The room was very clean and comfortable."

Reviewed on Sep 18, 2025

Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
7.2/10 Good! (1,000 reviews)
"Nice"

Reviewed on Sep 22, 2025

Get rates
Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Oct 19 to Oct 20
$172 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (898 reviews)
"Very easy check-in. Lovely staff, very friendly, and helpful. The only thing missing is a tea coffee maker in the room. Otherwise, everything else is excellent."

Reviewed on Sep 25, 2025

The Mountain Inn at Killington
See all 2,164 properties in Middletown Springs
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 Middletown Springs vacation package cost?
Offering great value package deals from $291 on Expedia, you'll be pleasantly surprised at how much a vacation to Middletown Springs costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middletown Springs?
You're likely to find lower prices and greater availability in April, May and October. Browse our cheap Middletown Springs vacation packages and you could score some excellent off-season deals.
How many days is enough for Middletown Springs?
Generally, a handful of days is enough to tick off the main sights during your Middletown Springs vacation. But if you want to have more time to unwind or go on day trips, think about extending your trip.
How to find the best Middletown Springs package deals?
Bagging a cheap Middletown Springs package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Middletown Springs package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Middletown Springs vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the flexibility to create a customized Middletown Springs vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Middletown Springs?
Score incredible discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Middletown Springs trip.
Does Expedia offer Book Now, Pay Later Middletown Springs vacation packages?
Secure your dream getaway to Middletown Springs with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up cheap 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.