Clarendon Square Inn

South End, just steps from Downtown and the Back Bay, is Boston’s trendy heart of brownstones, pretty squares, and a buzzing arts and restaurant scene. Favoured by a young, hip crowd, it’s perfect for experiencing the city like a local. Hotels here range from charming B&Bs to stylish boutique stays, many offering excellent value. Our experts have handpicked the best for design, service, and amenities—ideal for couples, families, or business travellers. Browse the collection to plan your stay.

For a boutique

The Revolution Hotel

  • The Revolution Hotel- Urban-chic loft vibes define this boutique stay, with airy rooms featuring wooden floors and striking cityscape wallpapers. Its buzzing restaurant draws a lively crowd, making it ideal for guests who enjoy contemporary design, social spaces, and a vibrant city atmosphere.
  • An intimate hideaway with just four rooms, Clarendon Square Inn is a boutique inn that exudes classic New England charm. Guests can unwind in the rooftop hot tub or sip from the honesty bar, making it perfect for couples seeking a quiet, romantic escape with stylish, understated interiors.

For great value

Staypineapple Boston

  • Staypineapple Boston is a playful retreat in Boston’s South End, featuring bold, colourful interiors and a lively on-site bar and restaurant. Rooms are snug yet inviting, with plush duvets and soft bathrobes. Guests can pedal around the city on provided bikes, making exploration effortless and fun. An affordable choice.

Still not sure?

The Best Hotels in South End, Boston

Clarendon Square Inn

Boston (South End)

A sophisticated spot, close to ‘restaurant row’ & the SoWa arts district. Tucked down a quiet street, this boutique hotel offers tranquility away from the city’s hustle and bustle and New England style in abundance. Great for culture seekers, food lovers and couples in search of a romantic weekend.

  • Sights nearby - Boston Common, the SoWa arts district, Tremont Street restaurants, Prudential Center’s Skywalk Observatory
  • Views - From the roof terrace over Boston's skyline
  • Romantic
  • Short break
from CA$174 for 1 room, 1 night including taxes & fees
Check availability on Expedia

The Revolution Hotel

Boston (South End)

This city bolt-hole sits at the intersection of Berkeley St and Appleton St in Boston’s South End. Inside, the modern guestrooms have a loft feel, with authentic wooden floors and cityscape wallpapers. The hotel hosts Cósmica, a stylish neighbourhood spot serving Cal-Mex specialities.

  • Local exploring - Set within easy walking distance of the best shops, bars and restaurants, this hotel is great for city exploring
  • Romantic Break - With stylish suites, a romantic restaurant and attentive staff, book this hotel for a chic couples' city break
  • City Style - With boutique interiors and a central city location, book this hotel for revolutionary Boston charm
  • Great walks - Walk the Freedom Trail, a 2.5-mile-long path through downtown Boston that passes by 16 locations significant to USA history
from CA$293 for 1 room, 1 night including taxes & fees
Check availability on Expedia

Staypineapple Boston

Boston (South End)

Quirky and fun hotel located in Boston's South End with a bar and restaurant. 55 rooms are compact but comfortable with cosy duvets and fluffy bathrobes. As well as dog-friendly and pineapple-themed, there are nice touches like complimentary morning coffee & afternoon treats, plus free bikes.

  • Local exploring - Enjoy South End's charming vibe, complete with Victorian Brownstones & local restaurants, or venture easily into the city centre
  • Restaurant - The restaurant is not open for breakfast, but there are great cafes and other options in the neighbourhood
  • Local markets - Head to SoWa Open Market to search for antiques and wares created by local artists
  • Great walks
from CA$215 for 1 room, 1 night including taxes & fees
Check availability on Expedia

Written by Katie Harris

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