Pessine Vacations from $1,495

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The Latest Pessine vacation packages

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

Hotel Brunelleschi

4 out of 5
Milan Centre
Price was $2,222, price is now $1,495 per person
$1,495
per person
Jan 17 - Jan 24
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milan (MXP)
8.8/10 Excellent! (1,440 reviews)

Magna Pars- L'Hotel à Parfum Small Luxury Hotels of the World

Magna Pars- L'Hotel à Parfum Small Luxury Hotels of the World

5 out of 5
Porta Genova
Price was $2,264, price is now $1,539 per person
$1,539
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milan (MXP)
9.4/10 Exceptional! (657 reviews)

Clerici Boutique Hotel

Clerici Boutique Hotel

4 out of 5
Milan Centre
Price was $2,899, price is now $2,030 per person
$2,030
per person
Dec 10 - Dec 17
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Milan (MXP)
9/10 Wonderful! (426 reviews)
Small boutique hotel with spacious clean rooms, helpful and attentive staff and very convenient location in the heart of old Milan.

Reviewed on Oct 20, 2026

Grand Hotel Royal e Golf

Grand Hotel Royal e Golf

5 out of 5
Courmayeur City Center
Price was $2,851, price is now $2,019 per person
$2,019
per person
Jan 13 - Jan 17
found 19 hours ago
Roundtrip flight included
New York (JFK) to Milan (MXP)
9.2/10 Wonderful! (168 reviews)
Location Breakfast

Reviewed on Sep 19, 2026

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

Palazzo Cordusio Gran Meliá – The Leading Hotels of the World

5 out of 5
Milan Centre
Price was $4,014, price is now $2,854 per person
$2,854
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milan (MXP)
9.4/10 Exceptional! (79 reviews)
Friendly staff, great location near high-end shopping and extremely well-maintained rooms. Food selection is awesome and restaurants have great selections.

Reviewed on Oct 31, 2026

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Pessine Hotel Deals

Phi Hotel Palio

Phi Hotel Palio

4 out of 5
Via Cavour 106 Asti AT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $114 total per night from Nov 19 to Nov 20
$114 total
Nov 19 - Nov 20
Total with taxes and fees
Phi Hotel Palio
Hotel Cavour Asti

Hotel Cavour Asti

2 out of 5
Piazza Marconi 18 Asti AT
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $72 total per night from Nov 8 to Nov 9
$72 total
Nov 8 - Nov 9
Total with taxes and fees
9/10 Wonderful! (140 reviews)
"Very nice staff. We checked out early in the morning and the staff even gave us a to go breakfast. Thank you so much"

Reviewed on Oct 3, 2026

Hotel Cavour Asti
Hotel Europa

Hotel Europa

3 out of 5
Piazza D Armi 5 Chivasso TO
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $106 total per night from Nov 6 to Nov 7
$106 total
Nov 6 - Nov 7
Total with taxes and fees
8.6/10 Excellent! (91 reviews)
"Great Hotel with very welcoming staff , Well looked after from checking in through to the lovely restaurant. Great Breakfast selection."

Reviewed on Oct 26, 2026

Hotel Europa
See all 688 properties in Pessine
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 Pessine Vacation Packages

Pessine Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao

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Frequently asked questions

How much does a Pessine vacation package cost?
Offering great value package deals from $1,495 on Expedia, you'll be surprised at how little a vacation to Pessine costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pessine?
You can typically find reduced prices and greater availability in November, December and January. Explore our cheap Pessine vacation packages and you could get some great off-season discounts.
How many days is enough for Pessine?
The ideal length for your Pessine vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you time to go to all the top sights and explore some hidden spots along the way.
How to find the best Pessine package deals?
Use Expedia's filter tool to help you find some of the best Pessine package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Pessine package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Pessine vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights individually. Better still, you can customize your Pessine escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Pessine?
If you're planning an impromptu Pessine vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Pessine vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Pessine trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.