Dream Stay – Five Bedroom Penthouse in Old Town

Dream Stay – Five Bedroom Penthouse in Old Town Overview

First Impressions

Walking up to Dream Stay – Five Bedroom Penthouse in Old Town, you immediately realize this isn’t your typical hotel experience. Located right on Suur-Karja street, you’re literally stepping into medieval Tallinn — I mean, the cobblestones are right outside your door. This four-star penthouse sits in what locals consider the absolute sweet spot of the Old Town, and honestly, that location score of 9.5 makes perfect sense once you’re here.

The Space Itself

The penthouse sprawls across the top floor with five separate bedrooms, which sounds massive until you actually walk through it — then it feels even bigger. Each room has its own character, some with those thick medieval walls you’d expect, others surprisingly modern. The main living area opens up beautifully, and you know what really struck me? The way they’ve managed to blend contemporary comfort with the building’s historic bones. There’s a full kitchen that actually works for cooking real meals, not just reheating leftovers.

Location Perks

Being right in the heart of Old Town means you’re maybe a two-minute walk from Town Hall Square — seriously, you can hear the street musicians from some of the windows. Raekoja Plats is where all the action happens, but here’s the thing locals know: Suur-Karja is just far enough off the main tourist drag that you get some peace at night. The medieval city wall is practically next door, and those morning walks along the ramparts before the crowds arrive? That’s when Tallinn really shows off.

What Works for Couples

I get why couples rate this place so highly — there’s something romantic about having an entire penthouse in a medieval city. The master bedroom has these amazing views over the red-tiled rooftops, and honestly, watching the sunrise over the Baltic from up there is pretty special. You’ve got space to spread out but also intimate corners where you can just sit with coffee and plan your day. The fact that you can walk to Toompea Castle or down to the harbor without dealing with trams or taxis… well, that’s the kind of convenience that makes a trip feel effortless.

Why Guests Love It

What really sets this place apart is how it lets you live like a local while staying in the most touristy part of town. You can grab groceries at the small shops nearby, cook dinner while looking out over medieval spires, then step outside for drinks at one of the cellar bars that have been serving people for centuries. The space works whether you’re traveling as a large group or just want plenty of room to breathe. Plus, there’s parking available, which — trust me — is gold in Old Town Tallinn where most streets barely fit a horse cart, let alone a rental car.

Apartments in Tallinn provide travelers with authentic local experiences, allowing them to explore traditional Estonian markets and cook with fresh Nordic specialties.

Dream Stay – Five Bedroom Penthouse in Old Town Accommodations

Reviews of Dream Stay – Five Bedroom Penthouse in Old Town

• Very Good – Karolina from Finland – June 23, 2025 (8/10)

  Location is great, there is only a short walk to museums, restaurants etc. Apartment was just as described and beds were comfortable. The noise in the street below couldn't be heard inside at all.
  
  What could be improved: There was no microwave oven, which was surprising but it wasn't listed in the amenities so I should have understood there won't be one.
  There was also only 2 dish washing tablets, not enough toilet paper and no kitchen paper or dishrag to clean table. Little things but annoying when they are missing.

• Wonderful – Vuorikoski from Finland – May 27, 2025 (9/10)

  We were quite pleased with the apartment. 5 bedrooms and spacious dining & relaxation area. We were a group of four so more space than we actually needed, this loft would accomodate e.g. 4 couples easily! Location 200m from Town Hall Square was perfect. Good value for the money and will definitely consider booking again for next trips.

• Wonderful – Danny from Sweden – March 17, 2025 (9/10)

  Location is perfect.
  Good price.
  Easy to get information about checkin and checkout
  Its old and perfect for shorter stays.
  
  What could be improved: Many stairs.

• Despite quality issues, this was still a great stay. Just certainly could do with some work – Breanna from Australia – January 16, 2025 (7/10)

  Location and size
  
  What could be improved: We couldn’t use the TV for the entirety of our stay despite people coming to fix it. We paid extra for a Christmas tree, but found bunches of it and old packaging in a cupboard. The kitchen facilities were very limited making it hard to cook. There was also doors missing on 2 bedrooms.

• Comfy flat in the heart of Old Town – Noelle from Switzerland – January 11, 2025 (7/10)

  The flat is within a nice walking distance from everything you want to see and do in Old Town. Even the views from the windows were nice, which came in handy for the New Year’s Eve fireworks. 🙂 The shared spaces were very comfortable and homey, and our people had plenty of living area to spread out into and not sit on top of each other. The hosts were super friendly and quick to support, and very sweet to decorate a small christmas tree for the season. We plan to come and stay again very soon, but definitely with a smaller group.
  
  What could be improved: Large groups beware! Yes, there are five beds in five rooms and an extra foldout is available, but not all ‘bedrooms‘ have doors. Those who did have doors slept very well, but the two couples who only had curtains (located directly off the kitchen/dining area) found it impossible to sleep if anyone was awake, not to mention privacy concerns. The flat is really cool! But if you‘re travelling with more than 6 people, it might not be as comfortable as you want/need/expect.

• Wonderful – Bgreta from Lithuania – November 21, 2024 (9/10)

  clean sheets and towels included.
  the place had space heaters so it was a savior on cold days, and heated floors in the toilet.
  
  What could be improved: the coffee machine didn't work properly, got charged from my deposit for using it. but the kettle worked so it wasn't too bad.
  two of the rooms are without doors, just curtains. one of them is almost inside the kichen.
  downstairs toilet is accessible by going through one of the bedrooms.
  there was not enough toilet paper for a three night stay.

• Very Good – Danah from United States – September 2, 2024 (8/10)

  Location!
  
  What could be improved: No A/C, they ask for deposit and bathroom need updates

• Great, spacious apartment on an excellent location – Kaj from Netherlands – November 16, 2023 (9/10)

  Great location in the city center and a nice spacious place. The kitchen and dining areas are great spots to play some cards and enjoy some beers with friends!
  
  What could be improved: Depending on which apartment I guess, but the 4 staircases were quite exhausting to climb up.

• Good – Felice from Italy – February 6, 2023 (7/10)

  What could be improved: Troppe scale!

• great location – Egle from Lithuania – November 21, 2022 (7/10)

  great location, spacious apartment for group of people traveling together
  
  What could be improved: one room was without any windows, two others are without doors so if you like privacy this would not be suitable for you. one of the bathrooms was in room so its not that comfortable when people are sleeping.

Surroundings