Discover Jake Rosenberg's hotel shortlist

  1. 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
  2. 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
  3. 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
  4. 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
  5. 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