Estonia Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Luxury vacation packages in Estonia

Price found within the past 48 hours. Click for updated prices.
Oru Hub Hotel Tallinn - Handwritten Collection

Oru Hub Hotel Tallinn - Handwritten Collection

Kesklinn
$328
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
8.6/10 Excellent! (430 reviews)
Swissotel Tallinn

Swissotel Tallinn

City Center
$410
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,086 reviews)
Fantastic hotel with lovely modern and spacious rooms, large open gym and in a great location. The icing on the cake would be to include the spa/pool as standard to achieve god tier hotel status. But this is a tiny weakness in an otherwise fabulous hotel (and more non issue if you are just visiting for a short stay/city break). Would highly recommend!

Reviewed on Sep 28, 2026

Hotel Telegraaf, Autograph Collection

Hotel Telegraaf, Autograph Collection

Old Town Tallinn
$540
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,000 reviews)
When choosing between the telegraaf and the Schlossle we vote the Schlossle. The staff were very unhelpful at the telegraaf and the rooms were very mediocre – carpeting, tired, and old and Ruth were smaller.

Reviewed on Sep 20, 2026

Merchants House Hotel

Merchants House Hotel

Old Town Tallinn
$381
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
8.6/10 Excellent! (1,001 reviews)
I'll have to research to give any bad or negative feedback. From the staff welcoming us and making sure we were comfortable with our questions and need met. The only thing I can say is our experience was "SUPERB".

Reviewed on Sep 23, 2026

The von Stackelberg Hotel Tallinn

The von Stackelberg Hotel Tallinn

City Center
$411
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
8.8/10 Excellent! (1,002 reviews)
Great location just 10 mins walk from the old town ..... And " olde worlde " style of hotel which fits in brilliantly with Tallin itself ... An beautiful room used for breakfast with an excellent choice offered .... Friendly staff ... would return and recommend

Reviewed on Aug 31, 2026

Don't see what you're looking for?
See all available trips from Columbus to Estonia
View all trips

5* Luxury vacations in Estonia

Price found within the past 48 hours. Click for updated prices.
Swissotel Tallinn

Swissotel Tallinn

City Center
$410
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,086 reviews)
Fantastic hotel with lovely modern and spacious rooms, large open gym and in a great location. The icing on the cake would be to include the spa/pool as standard to achieve god tier hotel status. But this is a tiny weakness in an otherwise fabulous hotel (and more non issue if you are just visiting for a short stay/city break). Would highly recommend!

Reviewed on Sep 28, 2026

Hotel Telegraaf, Autograph Collection

Hotel Telegraaf, Autograph Collection

Old Town Tallinn
$540
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,000 reviews)
When choosing between the telegraaf and the Schlossle we vote the Schlossle. The staff were very unhelpful at the telegraaf and the rooms were very mediocre – carpeting, tired, and old and Ruth were smaller.

Reviewed on Sep 20, 2026

Radisson Collection Hotel, Tallinn

Radisson Collection Hotel, Tallinn

City Center
$551
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.6/10 Exceptional! (1,217 reviews)
Exceptional hotel - so glad I decided to stay here, everything was to an incredibly high standard. Wonderful breakfast, attentive and friendly staff, lovely spa and rooftop bar. Would highly recommend to anyone staying in Tallinn

Reviewed on Sep 27, 2026

Don't see what you're looking for?
See all available trips from Columbus to Estonia
View all trips

3 Night Luxury vacations in Estonia

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

Merchants House Hotel

Old Town Tallinn
$381
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
8.6/10 Excellent! (1,001 reviews)
I'll have to research to give any bad or negative feedback. From the staff welcoming us and making sure we were comfortable with our questions and need met. The only thing I can say is our experience was "SUPERB".

Reviewed on Sep 23, 2026

Swissotel Tallinn

Swissotel Tallinn

City Center
$410
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,086 reviews)
Fantastic hotel with lovely modern and spacious rooms, large open gym and in a great location. The icing on the cake would be to include the spa/pool as standard to achieve god tier hotel status. But this is a tiny weakness in an otherwise fabulous hotel (and more non issue if you are just visiting for a short stay/city break). Would highly recommend!

Reviewed on Sep 28, 2026

Hotel Telegraaf, Autograph Collection

Hotel Telegraaf, Autograph Collection

Old Town Tallinn
$540
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Amsterdam (AMS) to Tallinn (TLL)
9.4/10 Exceptional! (1,000 reviews)
When choosing between the telegraaf and the Schlossle we vote the Schlossle. The staff were very unhelpful at the telegraaf and the rooms were very mediocre – carpeting, tired, and old and Ruth were smaller.

Reviewed on Sep 20, 2026

Don't see what you're looking for?
See all available trips from Columbus to Estonia
View all trips

4 Night Luxury vacations in Estonia

Price found within the past 48 hours. Click for updated prices.
Oru Hub Hotel Tallinn - Handwritten Collection

Oru Hub Hotel Tallinn - Handwritten Collection

Kesklinn
$965
per person
Nov 6 - Nov 10
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tallinn (TLL)
8.6/10 Excellent! (430 reviews)
Hotel Telegraaf, Autograph Collection

Hotel Telegraaf, Autograph Collection

Old Town Tallinn
$2,266
per person
Nov 6 - Nov 10
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tallinn (TLL)
9.4/10 Exceptional! (1,000 reviews)
When choosing between the telegraaf and the Schlossle we vote the Schlossle. The staff were very unhelpful at the telegraaf and the rooms were very mediocre – carpeting, tired, and old and Ruth were smaller.

Reviewed on Sep 20, 2026

Schlössle Hotel - Small Luxury Hotels of the World

Schlössle Hotel - Small Luxury Hotels of the World

Old Town Tallinn
$1,265
per person
Nov 6 - Nov 10
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Tallinn (TLL)
9.8/10 Exceptional! (845 reviews)
The best hotel of our month long trip! From check in to check out, everything was exceptional. Greeted with champagne or NA champagne, always a roaring fire in the exceptionally cozy lobby, porters available all the time to help carry luggage to/from rooms (there is no elevator due to the age and twists and turns of the building), delivering new pillows from the "pillow menu" at 10 pm, the turn-down service....really everything was wonderful. It is well worth the money to stay here. Breakfast is beyond exceptional with buffet style and made-to-order served in the medieval underground cellar. Parking would have been very difficult (or even driving in Old Town), so we waited until our departure day to rent a car at the port, which worked perfectly. One very small suggestion for the hotel: In the lobby there is a shared ottoman in front of the fire. Since it is upholstered there is a tray to rest one's drink. However the tray is very small and can only be used by one side of the ottoman at a time, so when more than one party is enjoying a glass of wine by the fire there is an awkward need to stand up and lean to the other people's side to share their tray. So just get another tray or a much larger flat surface.

Reviewed on Sep 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Estonia
View all trips

All you need to know about luxury vacations in Estonia

What can I expect from a luxury Estonia vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Estonia vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Estonia?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Estonia luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $328. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Estonia?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Estonia with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Estonia?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Estonia with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Estonia with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Estonia Hotels

Hotel Telegraaf, Autograph Collection

Hotel Telegraaf, Autograph Collection

Vene 9 Tallinn
  • 21 min walk from Port of Tallinn
$126 nightly
$143 total
Oct 29 - Oct 30
Total with taxes and fees
Hotel Telegraaf, Autograph Collection is a Tallinn luxury 5-star boutique property where you can treat yourself to plush bedding, designer toiletries, and more. ...
9.4/10 Exceptional! (1,000 reviews)
"When choosing between the telegraaf and the Schlossle we vote the Schlossle. The staff were very unhelpful at the telegraaf and the rooms were very mediocre – carpeting, tired, and old and Ruth were smaller."

Reviewed on Sep 20, 2026

Hotel Telegraaf, Autograph Collection
Swissotel Tallinn

Swissotel Tallinn

Tornimae 3 Tallinn
  • 16 min walk from Port of Tallinn
$107 nightly
$121 total
Oct 18 - Oct 19
Total with taxes and fees
Be treated to luxurious accommodations at Swissotel Tallinn, where you can enjoy amenities like plush bedding, designer toiletries, and more. The spa, indoor ...
9.4/10 Exceptional! (1,101 reviews)
"Fantastic hotel with lovely modern and spacious rooms, large open gym and in a great location. The icing on the cake would be to include the spa/pool as standard to achieve god tier hotel status. But this is a tiny weakness in an otherwise fabulous hotel (and more non issue if you are just visiting ..."

Reviewed on Sep 28, 2026

Swissotel Tallinn
Hotel St Petersbourg

Hotel St Petersbourg

Rataskaevu Str 7 Tallinn
  • 27 min walk from Port of Tallinn
Hotel St Petersbourg is one of the Tallinn luxury 5-star boutique properties where you can treat yourself to 24-hour room service, plush bedding, and more. The ...
Hotel St Petersbourg
See all 560 properties in Estonia
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.