Great — here are boutique-to-luxury hotels in Singapore that are especially good if you want cultural immersion and heritage-forward dining. For each I note what makes it a strong pick (history, neighbourhood, hotel restaurants or heritage dining collaborations) and which nearby cultural areas you can explore on foot.

1. Raffles Hotel Singapore — colonial landmark, classic heritage dining

• Why: Singapore’s most famous colonial “grand dame,” declared a national monument; historic venues include the Long Bar (home of the Singapore Sling) and the Tiffin Room (longstanding Indian dining tradition). Staying here is as much about history and stories as it is about service and opulence. (en.wikipedia.org)

2. The Fullerton Hotel Singapore / The Fullerton Bay Hotel — waterfront heritage buildings with local dining links

• Why: Housed in conserved civic buildings beside Marina Bay, the Fullerton properties foreground Singapore’s maritime and trading history. Their restaurants (Clifford Pier / Town Restaurant / Lighthouse collaborations) often stage “heritage” menus and hawker collaborations that spotlight local hawker classics in a historic setting. Great for easy walking access to the Civic District, Boat Quay and the full museum circuit. (en.wikipedia.org)

3. Grand Hyatt Singapore — established hotel that celebrates local flavours (Straits Cafe)

• Why: The Grand Hyatt’s Straits Cafe is known for heritage-style buffets and “Straits” (Peranakan / local) dishes; staying here puts you in the Orchard / Museum corridor with good access to Peranakan and colonial sites. Good if you want a big-hotel base with a strong local-food offering. (looneypalace.com)

4. Hotel Fort Canning — history-rich conservation hotel with park setting and local-inspired menus

• Why: Built on historic Fort Canning Hill (site of colonial administration and much older heritage), the hotel integrates archaeological displays and offers The Salon and Tisettanta lounge with locally influenced dishes and themed dining. Excellent if you want quieter, history-focused immersion near the civic and arts districts. (scribd.com)

5. The Clan Hotel (Keong Saik / Telok Ayer area) — shophouse heritage, intimate boutique stays near Chinatown/Keong Saik dining scene

• Why: Keong Saik and nearby shophouse districts are among Singapore’s conserved heritage quarters; boutique hotels here (shophouse conversions and clan-house areas) put you right in the middle of Chinatown, clan associations, and an eclectic mix of heritage restaurants and innovative modern dining outposts. Great for walking food/heritage trails. (scarletscribs.wordpress.com)

6. Naumi / Keong Saik–area boutique hotels (heritage townhouse conversions) — intimate, design-forward stays in conserved buildings

• Why: Naumi and similar boutique properties are often conversions of heritage townhouses/shophouses and sit within culturally rich neighbourhoods (Little India, Chinatown, Kampong Glam depending on property). They offer a boutique, local-neighbourhood feel and quick access to hawker centres and heritage eateries. (en.wikipedia.org)

Practical notes and tips

• Best neighbourhoods for heritage dining and immersion: Chinatown / Keong Saik (Chinese clan-house, Peranakan touches, Michelin hawker stalls nearby), Kampong Glam / Arab Street (Malay-Arab heritage, Middle Eastern cuisine), Katong / Joo Chiat (Peranakan food), and the Civic District / Boat Quay / Clarke Quay (historic piers, colonial-era buildings, Fullerton area). (scarletscribs.wordpress.com)
• Look for hotels that run “heritage” dining pop-ups, hawker collaborations, or museum/historic tours — those programs rotate by date/season, so check the hotel’s current events and dining pages before booking. (Hotel pages and recent press releases will show current collaborations.) (ordinarypatrons.com)

Want me to:

• Narrow this to a specific budget (luxury vs boutique vs midrange)?
• Suggest exact neighbourhood walking itineraries (e.g., where to eat for Peranakan, where to find historic clan houses) with map-based walking distances from a chosen hotel?

If you want I can also check current availability, menus, or any heritage dining events for specific dates — I’ll look those up.