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
Tallinn City Apartments Old Town Suites From US $161
         

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9.6 (372 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety
Heritage Brick Studio by Rotermann City Apts From US $62
         

10.0 (6 Reviews)
Apartment
  • TV
  • View
  • Wheelchair Accessible
Distillery Factory Loft by Rotermann City Apts From US $86
         

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

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

10.0 (2 Reviews)
Apartment
  • TV
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Toompea Castle Hideaway From US $164
         

10.0 (2 Reviews)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities

Luxury Places to Stay in Old Town

Over 358+ 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)
Apartment
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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)
Apartment
  • Air Conditioner
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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)
Apartment
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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 $182
         

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9.4 (1000 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hotel Telegraaf, Autograph Collection From US $258
         

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9.1 (880 Reviews)
Hotel
  • 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 $84
         

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8.4 (1001 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 (790 Reviews)
Hotel
  • Parking
  • Pool
  • TV
Quadruple room with shared facilities - Old Town From US $82
         

Pet-Friendly Vacation Rentals in Old Town

Over 56+ Pet-Friendly Vacation Rentals in or Near Old Town
Luxury apartment in the heart of Old Town From US $61
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
15th Century Flat with Parking, High Ceilings From US $139
         

10.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • TV
Luxury 2BD apartment in City Center From US $247
         

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9.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Bedding/Linens
Home cinema/2-bed, 2-bath/Free Private Parking From US $229
         

New
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Classy central flat/2-BR/private parking/Smart TV From US $215
         

New
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  • Pet Friendly
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  • Bedding/Linens
2BR/parking garage/Wi-Fi/next to Old Town From US $169
         

New
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  • Pet Friendly
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12 guests/70m2/center of Old Town/WiFi/Streaming From US $164
         

New
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Spacious luxury all inclusive old town flat From US $161
         

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

Large Vacation Homes & Villas in Old Town

Over 61+ Large Vacation Homes & Villas in or Near Old Town
The Knight House From US $48
         

7.1 (942 Reviews)
Hostel
  • Balcony/Terrace
  • Child Friendly
  • Internet
Prime Tallinn- Suur-Karja 4 From US $324
         

New
Apartment
  • TV
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Tallinn City Apartments Town Hall Square From US $88
         

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9.0 (234 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
Estonishing Stay Mere Residence From US $342
         

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

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8.6 (148 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety
12 guests, 70m2, center of Old Town, Wi-Fi, Streaming From US $112
         

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10.0 (1 Review)
Apartment
  • Security/Safety
  • Guest Services
  • Child Friendly
Tallinn City Apartments 4 bedroom Toompea Old Town From US $438
         

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9.9 (8 Reviews)
Apartment
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  • Guest Services
Tallinn Old Hanza Apartments From US $71
         

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9.8 (25 Reviews)
Apartment
  • Parking
  • View
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Old Town

Over 28+ Wheelchair Accessible Vacation Homes in or Near Old Town
Angleterre Apartments From US $52
         

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8.7 (1059 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Accessibility
Cozy 1-bedroom apartment in awesome Tallinn with WiFi From US $305
         

10.0 (1 Review)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Angleterre Apartments From US $73
         

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8.8 (492 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
DICTUMFACTUM RESIDENCE 2BedRoom From US $168
         

10.0 (1 Review)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
Nunne Boutique Hotel From US $69
         

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9.8 (1186 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
DICTUMFACTUM Old Town - Suur Karja with WiFi From US $172
         

New
Apartment
  • TV
  • 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 245+ Old Town Varoom and Airbnb Places to Stay Under $200
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 Toompea Old Town From US $89
         

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9.2 (217 Reviews)
Apartment
  • Parking
  • Bedding/Linens
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Luxury Apartment in Prime Area From US $190
         

New
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  • TV
  • Bedding/Linens
Vene 19 Heritage Residence with sauna
New
From US $189
         

New
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
DICTUMFACTUM Modern Apartment Viru Gates From US $180
         

Dictumfactum Love Nest on Pikk From US $145
         

New
Apartment
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  • Security/Safety
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Center of Old Town, historic view, open floorplan From US $142
         

New
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  • Pet Friendly
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Old Town

Over 26+ Instantly Bookable Vacation Homes in or Near Old Town
DictumFactum – Noble Old Town Tallinn From US $1,477
         

New
Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
DictumFactum – Noble Old Town Tallinn From US $219
         

New
Apartment
  • TV
  • Security/Safety
  • Bedding/Linens
Old Town design studio/3 min to Christmas market
New
From US $117
         

New
Apartment
  • Pet Friendly
  • Security/Safety
  • Bedding/Linens
Beyond Viru Gates- 1-bedroom apartment From US $89
         

New
Apartment
  • View
  • Ocean View
  • Security/Safety
Stay in a real medieval tower (lower floors) From US $85
         

New
Apartment
  • Parking
  • Security/Safety
  • Fireplace/Heating

About Old Town Vacation Rentals

With more than 367 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 540.73 ft² on average, with prices averaging $173 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 296
Hotels with Suites 46
Vacation Homes 15
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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