Anna Vacations from $926

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The Latest Anna vacation packages

Price found within the past 48 hours. Click for updated prices.
Blacksmith Old Town Apartments

Blacksmith Old Town Apartments

3.5 out of 5
Old Town Tallinn
Price was $1,020, price is now $926 per person
$926
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tallinn (TLL)
8.4/10 Very Good! (15 reviews)
It is located in the bottom area of the old town and is a short walk to many bars and restaurants located there. It bigger than a hotel room and the small kitchen allows you to make small meals. There is cutlery, plates, bowls and cooking utensils. An ideal base camp to explore the city but not a place to sit in comfort

Reviewed on Sep 7, 2024

The Burman Hotel

The Burman Hotel

5 out of 5
Old Town Tallinn
Price was $1,753, price is now $1,384 per person
$1,384
per person
Dec 15 - Dec 20
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Tallinn (TLL)
9.8/10 Exceptional! (11 reviews)
When we go back to Tallin we definitely will stay in this beautiful hotel again. Very happy. As it was only new there were a couple of hiccups but all was fabulous.

Reviewed on Sep 13, 2025

Schlössle Hotel - Small Luxury Hotels of the World

Schlössle Hotel - Small Luxury Hotels of the World

5 out of 5
Old Town Tallinn
Price was $1,990, price is now $1,731 per person
$1,731
per person
Dec 15 - Dec 20
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Tallinn (TLL)
9.6/10 Exceptional! (756 reviews)
hotel needs to inform gets that there is no elevator. i was on the 3rd floor and had difficulty navigating but staff was quick to change me next day!

Reviewed on Sep 17, 2025

Nunne Boutique Hotel

Nunne Boutique Hotel

4 out of 5
Old Town Tallinn
Price was $1,342, price is now $1,184 per person
$1,184
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tallinn (TLL)
9.8/10 Exceptional! (973 reviews)
Great small hotel with great staff !

Reviewed on Oct 6, 2025

8ERA Business Executive Rotermanni Apts

8ERA Business Executive Rotermanni Apts

3.5 out of 5
City Center
Price was $1,029, price is now $929 per person
$929
per person
Dec 15 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tallinn (TLL)
9.2/10 Wonderful! (55 reviews)
Katja was very helpful on WhatsApp before and during the trip with requests and queries. We loved having access to the rooftop terrace and the view of the old town. Size of the apartment was great and the kitchen was well equipped. My only suggestion would be that, for rooms with access to the rooftop through a skylight, it would be good to offer in advance the possibility of covering the skylight for light sleepers like me. The solution to cover it was offered straight away when I asked if anything could be done. Great stay in a great area of Tallinn. Tänan

Reviewed on Aug 19, 2025

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Anna Hotel Deals

SagaCamp ehf

SagaCamp ehf

2 out of 5
Vio Austurveg, Laane, Harju County
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SagaCamp ehf
Paide Old Town Suite Sophia

Paide Old Town Suite Sophia

Paide
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Paide Old Town Suite Sophia
See all 2 properties in Anna
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.

Anna Essential Information

Language
Estonian
Currency
Euros
Top Sights
Ajakeskus Wittenstein, Sargvere Manor and Holy Cross Church

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Frequently asked questions

How much does an Anna vacation package cost?
Offering great value package deals from $926 on Expedia, you'll be surprised at how little a vacation to Anna costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Anna?
November, December and January are great times to search for cheap Anna vacation packages. Traveling in quieter months means you can generally find lower prices on hotels and flights.
How many days is enough for Anna?
Typically, a handful of days is enough to go to the major sights during your Anna vacation. However, if you'd like to have some time to unwind or take day tours, think about extending your trip.
How to find the best Anna package deals?
Bagging a cheap Anna package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Anna package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Anna vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can tailor your Anna getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Anna?
If you've got your Anna travel dates locked in, book early to grab some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for setting off on a whim.
Does Expedia offer Book Now, Pay Later Anna vacation packages?
Your Anna break should be an escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.