Discover Jake Rosenberg's hotel shortlist

Tuscany, Italy

Monteverdi Tuscany

Style

Mellow mediaeval village

Setting

Colourful Castiglioncello

Price per night from (ex tax)$2,443.02

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)

Smith Extra
A glass of prosecco and a selection of local cheeses and meats at Enoteca
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Health & safety New safety measures are in place at this hotel. Read more here
St Barths, St. Barthélemy

Hotel Christopher

Style

Haute Caribbean

Setting

Ocean-view Pointe Milou

Price per night from (ex tax)$560.83

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)

Smith Extra
House-made treats from the chef
View hotel
Health & safety New safety measures are in place at this hotel. Read more here
Santorini, Greece

Kapari Natural Resort

Style

Neutral shades, cool caves

Setting

Volcanic viewpoint

Price per night from (ex tax)$465.29

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)

Smith Extra
Free pick-up from either the airport or seaport and a plate of fresh fruit on arrival
View hotel
Health & safety New safety measures are in place at this hotel. Read more here
New York, United States

The Bowery

Style

Retro glamour

Setting

Post-punk East Village

Price per night from (ex tax)$325.00

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)

Smith Extra
A bottle of wine
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STAY FLEXIBLE Cancel with 48 hours notice
Toronto, Canada

The Drake

Style

Cool, cultural cutting-edge

Setting

Art and Design District of Parkdale

Price per night from (ex tax)$172.18

Why book with us?

Best-price guarantee

Found your stay for less elsewhere? We'll match the price and give you a £50 voucher.

Free Smith Extras on arrival

From a bottle of champagne, to a spa treatment or a cookery class, you’ll get a little extra thank you with every booking

Here for you 24/7

Personal service from Smith24, our in-house travel specialists, 1 800 464 2040

Anonymously reviewed

Every hotel is reviewed by undercover tastemakers (and their partners)

Smith Extra
A bottle of Starving Artist house red or white wine in your room on arrival
View hotel