Top Winter Vacations - Vacation Rentals in Old Town

Stunning Old Town Getaway with Sauna! From US $139
         

10.0 (11 Reviews)
Apartment
  • TV
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Pagari Residence From US $50
         

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9.6 (34 Reviews)
Apartment
  • Parking
  • Child Friendly
  • Internet
Spacious luxury all inclusive old town flat From US $199
         

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Modern loft apartment right next to Old Town From US $86
         

10.0 (6 Reviews)
Apartment
  • TV
  • View
  • Wheelchair Accessible
Stylish Historic Loft - Your Comfy Old Town Stop! From US $87
         

10.0 (3 Reviews)
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  • Parking
  • TV
  • Security/Safety
Your Dream Flat in the City Centre + Free Parkingn From US $78
         

10.0 (3 Reviews)
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  • Parking
  • TV
  • Balcony/Terrace
Town Hall Square Apartment. Best Location in Town! From US $165
         

10.0 (2 Reviews)
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  • TV
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Tallinn City Apartment From US $91
         

10.0 (2 Reviews)
Apartment
  • Pet Friendly
  • TV
  • Security/Safety

Luxury Places to Stay in Old Town

Over 361+ Luxury Places to Stay in or Near Old Town
Stay in a real medieval tower, lower floors From US $1,599
         

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9.5 (2 Reviews)
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Luxury apartment Baron fon Fersen From US $989
         

10.0 (3 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Transportation/Shuttle
Old Town - Demini Apartment From US $817
         

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8.4 (126 Reviews)
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Old Town - Lai Apartment From US $790
         

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8.5 (167 Reviews)
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Dictumfactum Love Nest on Pikk From US $699
         

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8.8 (4 Reviews)
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Tallinn City Apartments 4 bedroom with sauna and 2 bathroom From US $686
         

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9.7 (101 Reviews)
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Tallinn City Apartments - Old Town Townhouse From US $620
         

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9.6 (66 Reviews)
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AirHome - Royal Family From US $592
         

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New
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  • Pet Friendly
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Top-Rated Vacation Rentals with a Pool in Old Town

Over 11+ Top-Rated Vacation Rentals with a Pool in or Near Old Town
Hotel Telegraaf, Autograph Collection From US $167
         

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9.4 (1002 Reviews)
Hotel
  • Air Conditioner
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  • Pool
Hotel Telegraaf, Autograph Collection From US $258
         

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9.1 (899 Reviews)
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  • Air Conditioner
  • Parking
  • Pet Friendly
Hotel Regent Tallinn From US $159
         

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8.9 (454 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Braavo Spa Hotel From US $99
         

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8.5 (1455 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Kalev Spa Hotel & Waterpark From US $111
         

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8.4 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Kalev Spa Hotel & Waterpark From US $173
         

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8.3 (4486 Reviews)
Hotel
  • Air Conditioner
  • Pet Friendly
  • Pool
Braavo Spa Hotel From US $358
         

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7.6 (787 Reviews)
Hotel
  • Parking
  • Pool
  • TV
Quadruple room with shared facilities - Old Town From US $82
         

Pet-Friendly Vacation Rentals in Old Town

Over 55+ Pet-Friendly Vacation Rentals in or Near Old Town
Luxury Villa style/best view/terrace/BBQ/2BR/2bath From US $292
         

New
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Luxury Suites in the Heart of Medieval Tallinn Old Town From US $555
         

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10.0 (1 Review)
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  • Pet Friendly
  • Security/Safety
  • Child Friendly
Luxury 2BD apartment in City Center From US $280
         

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9.0 (2 Reviews)
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  • Pet Friendly
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Home cinema/2-bed, 2-bath/Free Private Parking From US $208
         

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Spacious luxury all inclusive old town flat From US $162
         

New
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Classy central flat/2-BR/private parking/Smart TV From US $155
         

New
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  • Pet Friendly
  • Security/Safety
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2-bed, 1.5-bath Old Town Flat with Sauna and Bar From US $139
         

See More Pet-Friendly Vacation Rentals in Old Town on PetFriendly.io

Large Vacation Homes & Villas in Old Town

Over 63+ Large Vacation Homes & Villas in or Near Old Town
Prime Tallinn- Suur-Karja 4 From US $323
         

New
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The Knight House From US $48
         

7.1 (942 Reviews)
Hostel
  • Balcony/Terrace
  • Child Friendly
  • Internet
Tallinn City Apartments Town Hall Square From US $88
         

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9.0 (232 Reviews)
Apartment
  • Parking
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  • Balcony/Terrace
12 guests/70m2/center of Old Town/WiFi/Streaming From US $134
         

New
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Estonishing Stay Mere Residence From US $342
         

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8.0 (164 Reviews)
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  • Wheelchair Accessible
  • Internet
Tallinn City Apartments Harju Residence From US $105
         

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8.6 (146 Reviews)
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Tallinn City Apartments 4 bedroom Toompea Old Town From US $438
         

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9.9 (8 Reviews)
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Family Apartment From US $174
         

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9.7 (141 Reviews)
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  • Air Conditioner
  • Parking
  • Accessibility

Wheelchair Accessible Vacation Homes in Old Town

Over 27+ Wheelchair Accessible Vacation Homes in or Near Old Town
DICTUMFACTUM RESIDENCE 2BedRoom From US $217
         

10.0 (1 Review)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Angleterre Apartments From US $52
         

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8.8 (1103 Reviews)
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  • Parking
  • Wheelchair Accessible
  • Accessibility
Angleterre Apartments From US $79
         

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8.8 (490 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Two-level Loft Apartments in Swedish style 7 From US $119
         

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8.7 (122 Reviews)
Apartment
  • Wheelchair Accessible
  • Accessibility
  • Security/Safety
Nunne Boutique Hotel From US $79
         

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9.8 (1114 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
DICTUMFACTUM Old Town - Suur Karja with WiFi From US $197
         

New
Apartment
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  • Wheelchair Accessible
  • Accessibility
Amazing view in the heart of Tallinn From US $76
         

4.7 (3 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Balcony/Terrace

Old Town Varoom and Airbnb Places to Stay Under $200

Over 246+ Old Town Varoom and Airbnb Places to Stay Under $200
Toompea Castle Hideaway From US $164
         

10.0 (1 Review)
Apartment
  • Security/Safety
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Modern charm in old town From US $183
         

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10.0 (16 Reviews)
Apartment
  • Security/Safety
  • Sports/Activities
  • Fireplace/Heating
Tallinn City Apartments Old Town Suites From US $161
         

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9.6 (369 Reviews)
Apartment
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  • TV
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Luxury Apartment in Prime Area From US $188
         

New
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Beyond Viru Gates- 1-bedroom apartment From US $139
         

New
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  • View
  • Ocean View
  • Security/Safety
2BR/Balcony/parking garage/Wi-Fi/next to Old Town From US $133
         

New
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  • Pet Friendly
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Instantly Bookable Vacation Homes in Old Town

Over 18+ Instantly Bookable Vacation Homes in or Near Old Town
DictumFactum – Noble Old Town Tallinn From US $1,477
         

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DictumFactum – Noble Old Town Tallinn From US $245
         

New
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DICTUMFACTUM Modern Apartment Viru Gates From US $232
         

1-bedroom Old Town apartment From US $116
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Stay in a real medieval tower (lower floors) From US $90
         

New
Apartment
  • Parking
  • Security/Safety
  • Fireplace/Heating
Family Room with shared facilities - Old town From US $83
         

New
House
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1-Bedroom apartment in the historic Old Town From US $76
         

New
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  • TV
  • Security/Safety
  • Wellness Facilities

About Old Town Vacation Rentals

With more than 370 Old Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Topwintervacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Old Town.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Topwintervacations Old Town, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Old Town. Places to stay near Old Town are 549.7 ft² on average, with prices averaging $174 a night.

Topwintervacations makes it easy and safe to find and compare vacation rentals in Old Town with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Old Town

Type Count
Holiday Apartments 297
Hotels with Suites 47
Vacation Homes 16
Hostels 9

Use these Quick Filters to Find a Vacation Rental in Old Town

Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Old Town.

Weather in Old Town

View the weather forecast for Old Town before booking your Old Town Vacation Rentals to confirm your best time to go.

December - February
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March - May
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June - August
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September - November
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